#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:07:58 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294409 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/34/7133432.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_7133432
loop_
_publ_author_name
'Zhang, Jinhui'
'Mao, Lihua'
'Liu, Chao'
'Tan, Xiangwen'
'Wu, Jiahao'
'Wei, Xuefeng'
'Wu, Wanqing'
'Jiang, Huanfeng'
_publ_section_title
;
 Palladium-catalyzed 1,1-aminoxylation of 3-butenoic acid with
 2-alkynylanilines.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9404
_journal_page_last               9407
_journal_paper_doi               10.1039/d4cc03099k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 F N O2'
_chemical_formula_sum            'C18 H14 F N O2'
_chemical_formula_weight         295.30
_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     dual
_audit_creation_date             2022-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-03-01 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                104.289(2)
_cell_angle_beta                 110.312(2)
_cell_angle_gamma                107.388(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2770(6)
_cell_length_b                   9.5602(6)
_cell_length_c                   9.7665(6)
_cell_measurement_reflns_used    2054
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.185
_cell_measurement_theta_min      2.584
_cell_volume                     713.26(8)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8815
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.584
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1628 before and 0.0604 after correction. The Ratio of minimum to maximum transmission is 0.7868. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0529
_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)+(0.0358P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1888
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03099k2.cif
_cod_data_source_block           zj1018_0m
_cod_depositor_comments          'Adding full bibliography for 7133432.cif.'
_cod_database_code               7133432
_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   0.995
_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 Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C18(H18), C8(H8), C12(H12), C6(H6), C14(H14), C16(H16),
 C15(H15)
;
_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
O1 O 0.63346(18) 0.58846(16) 0.23119(16) 0.0371(4) Uani 1 1 d . . . . .
F1 F 0.22074(17) -0.23241(16) 0.18325(17) 0.0620(4) Uani 1 1 d . . . . .
O2 O 0.6319(2) 0.71645(18) 0.06985(18) 0.0573(5) Uani 1 1 d . . . . .
N1 N 0.7491(2) 0.5042(2) 0.43343(19) 0.0340(4) Uani 1 1 d . . . . .
C4 C 0.6896(3) 0.4681(2) 0.2669(2) 0.0340(5) Uani 1 1 d . . . . .
H4 H 0.591093 0.361021 0.206145 0.041 Uiso 1 1 calc R . . . .
C17 C 0.8653(3) 0.6548(2) 0.5531(2) 0.0343(5) Uani 1 1 d . . . . .
C9 C 0.4189(3) 0.1817(3) 0.4470(3) 0.0415(6) Uani 1 1 d . . . . .
H9 H 0.404155 0.250464 0.524421 0.050 Uiso 1 1 calc R . . . .
C10 C 0.5511(3) 0.2433(2) 0.4118(2) 0.0344(5) Uani 1 1 d . . . . .
C5 C 0.5706(3) 0.1393(3) 0.2991(3) 0.0393(5) Uani 1 1 d . . . . .
H5 H 0.661295 0.178939 0.274571 0.047 Uiso 1 1 calc R . . . .
C1 C 0.6785(3) 0.6285(3) 0.1238(2) 0.0415(6) Uani 1 1 d . . . . .
C11 C 0.6702(3) 0.4120(2) 0.5001(2) 0.0352(5) Uani 1 1 d . . . . .
C13 C 0.8575(3) 0.6553(3) 0.6938(2) 0.0407(6) Uani 1 1 d . . . . .
C18 C 0.9709(3) 0.7881(3) 0.5463(3) 0.0417(6) Uani 1 1 d . . . . .
H18 H 0.971968 0.787445 0.449207 0.050 Uiso 1 1 calc R . . . .
C3 C 0.8213(3) 0.4717(3) 0.2069(3) 0.0452(6) Uani 1 1 d . . . . .
H3A H 0.937683 0.537147 0.294497 0.054 Uiso 1 1 calc R . . . .
H3B H 0.809703 0.362778 0.156858 0.054 Uiso 1 1 calc R . . . .
C8 C 0.3080(3) 0.0213(3) 0.3708(3) 0.0468(6) Uani 1 1 d . . . . .
H8 H 0.218376 -0.020661 0.395828 0.056 Uiso 1 1 calc R . . . .
C7 C 0.3310(3) -0.0748(3) 0.2590(3) 0.0444(6) Uani 1 1 d . . . . .
C12 C 0.7353(3) 0.5018(3) 0.6576(2) 0.0435(6) Uani 1 1 d . . . . .
H12 H 0.704440 0.467690 0.730901 0.052 Uiso 1 1 calc R . . . .
C6 C 0.4599(3) -0.0212(3) 0.2217(3) 0.0440(6) Uani 1 1 d . . . . .
H6 H 0.473833 -0.091742 0.144984 0.053 Uiso 1 1 calc R . . . .
C14 C 0.9646(3) 0.7927(3) 0.8335(3) 0.0524(7) Uani 1 1 d . . . . .
H14 H 0.962638 0.795068 0.930667 0.063 Uiso 1 1 calc R . . . .
C2 C 0.7817(3) 0.5458(3) 0.0863(3) 0.0545(7) Uani 1 1 d . . . . .
H2A H 0.887459 0.622700 0.096168 0.065 Uiso 1 1 calc R . . . .
H2B H 0.716765 0.462919 -0.022925 0.065 Uiso 1 1 calc R . . . .
C16 C 1.0747(3) 0.9220(3) 0.6863(3) 0.0479(6) Uani 1 1 d . . . . .
H16 H 1.149006 1.014491 0.685206 0.058 Uiso 1 1 calc R . . . .
C15 C 1.0724(3) 0.9238(3) 0.8284(3) 0.0529(7) Uani 1 1 d . . . . .
H15 H 1.146214 1.016633 0.922896 0.063 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'
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
C1 O1 C4 110.60(16) . . ?
C17 N1 C4 124.35(17) . . ?
C11 N1 C4 125.20(17) . . ?
C11 N1 C17 108.42(16) . . ?
O1 C4 C3 105.51(16) . . ?
N1 C4 O1 108.48(15) . . ?
N1 C4 C3 115.48(17) . . ?
C13 C17 N1 107.54(19) . . ?
C18 C17 N1 130.41(19) . . ?
C18 C17 C13 122.03(19) . . ?
C8 C9 C10 121.0(2) . . ?
C9 C10 C5 118.2(2) . . ?
C9 C10 C11 119.3(2) . . ?
C5 C10 C11 122.4(2) . . ?
C6 C5 C10 121.2(2) . . ?
O1 C1 C2 110.36(19) . . ?
O2 C1 O1 120.5(2) . . ?
O2 C1 C2 129.2(2) . . ?
N1 C11 C10 123.27(18) . . ?
C12 C11 N1 108.33(19) . . ?
C12 C11 C10 128.2(2) . . ?
C17 C13 C12 107.13(18) . . ?
C17 C13 C14 119.0(2) . . ?
C14 C13 C12 133.9(2) . . ?
C16 C18 C17 117.5(2) . . ?
C2 C3 C4 103.75(18) . . ?
C7 C8 C9 118.4(2) . . ?
C8 C7 F1 118.2(2) . . ?
C6 C7 F1 118.7(2) . . ?
C6 C7 C8 123.0(2) . . ?
C11 C12 C13 108.6(2) . . ?
C7 C6 C5 118.2(2) . . ?
C15 C14 C13 119.3(2) . . ?
C1 C2 C3 105.14(18) . . ?
C18 C16 C15 121.4(2) . . ?
C14 C15 C16 120.8(2) . . ?
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
O1 C4 1.465(2) . ?
O1 C1 1.352(3) . ?
F1 C7 1.366(2) . ?
O2 C1 1.204(3) . ?
N1 C4 1.434(2) . ?
N1 C17 1.403(3) . ?
N1 C11 1.401(3) . ?
C4 C3 1.523(3) . ?
C17 C13 1.399(3) . ?
C17 C18 1.389(3) . ?
C9 C10 1.390(3) . ?
C9 C8 1.388(3) . ?
C10 C5 1.392(3) . ?
C10 C11 1.467(3) . ?
C5 C6 1.388(3) . ?
C1 C2 1.493(3) . ?
C11 C12 1.364(3) . ?
C13 C12 1.427(3) . ?
C13 C14 1.403(3) . ?
C18 C16 1.386(3) . ?
C3 C2 1.514(3) . ?
C8 C7 1.366(3) . ?
C7 C6 1.361(3) . ?
C14 C15 1.375(3) . ?
C16 C15 1.391(3) . ?
