#------------------------------------------------------------------------------
#$Date: 2023-05-05 02:19:08 +0200 (Fri 05 de May de 2023) $
#$Revision: 283065 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/11/7131160.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_7131160
loop_
_publ_author_name
'Su, Jingwen'
'Guo, Wenbin'
'Liu, Yi'
'Kong, Lichun'
'Zheng, Hanliang'
'Zhu, Gangguo'
_publ_section_title
;
 Cu-catalyzed cascade difluoroalkylation/5-endo
 cyclization/β-fluorine cleavage of ynones.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1821
_journal_page_last               1824
_journal_paper_doi               10.1039/d2cc06068j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C19 H24 F N O2'
_chemical_formula_sum            'C19 H24 F N O2'
_chemical_formula_weight         317.39
_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             2022-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-26 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                98.240(2)
_cell_angle_beta                 98.468(2)
_cell_angle_gamma                91.823(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2396(2)
_cell_length_b                   9.9099(4)
_cell_length_c                   14.5635(6)
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      68.028
_cell_measurement_theta_min      5.854
_cell_volume                     880.22(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1314
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10704
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.196
_diffrn_reflns_theta_min         5.854
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.057(7)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0682
_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)+(0.0974P)²+0.2087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1828
_refine_ls_wR_factor_ref         0.2032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2453
_reflns_number_total             3199
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc06068j2.cif
_cod_data_source_block           20221019s_0m
_cod_depositor_comments
'Adding full bibliography for 7131160--7131161.cif.'
_cod_database_code               7131160
_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   0.843
_shelx_estimated_absorpt_t_min   0.811
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00C), C00G(H00F,H00G), C00K(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00I(H00K), C00J(H00L)
2.d Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J), C00L(H00O,H00P,H00Q), C00M(H00R,H00S,H00T), C00N(H00U,
 H00V,H00W)
;
_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
F001 F 0.2560(3) 0.65240(14) 0.38811(10) 0.0726(5) Uani 1 1 d . . . . .
O002 O 0.2644(3) 0.50537(19) 0.54035(12) 0.0679(5) Uani 1 1 d . . . . .
O003 O -0.0028(3) 0.4850(2) 0.18837(13) 0.0703(6) Uani 1 1 d . . . . .
N004 N 0.3173(3) 0.6009(2) 0.19268(14) 0.0626(6) Uani 1 1 d . . . . .
C005 C 0.1662(3) 0.2710(2) 0.32146(15) 0.0519(6) Uani 1 1 d . . . . .
H005 H 0.009206 0.258193 0.300742 0.062 Uiso 1 1 calc R U . . .
C006 C 0.2111(3) 0.4159(2) 0.37403(15) 0.0515(6) Uani 1 1 d . . . . .
C007 C 0.2751(3) 0.2351(2) 0.23565(15) 0.0519(6) Uani 1 1 d . . . . .
C008 C 0.2193(4) 0.5272(2) 0.33505(16) 0.0543(6) Uani 1 1 d . . . . .
C009 C 0.2217(4) 0.4110(2) 0.47674(16) 0.0567(6) Uani 1 1 d . . . . .
C00A C 0.1706(4) 0.5361(2) 0.23182(16) 0.0546(6) Uani 1 1 d . . . . .
C00B C 0.4810(4) 0.2879(2) 0.23030(18) 0.0569(6) Uani 1 1 d . . . . .
H00B H 0.555775 0.347409 0.280912 0.068 Uiso 1 1 calc R U . . .
C00C C 0.2256(4) 0.1790(2) 0.39986(17) 0.0588(6) Uani 1 1 d . . . . .
C00D C 0.1686(4) 0.1448(3) 0.15953(18) 0.0626(6) Uani 1 1 d . . . . .
H00D H 0.030751 0.107932 0.161596 0.075 Uiso 1 1 calc R U . . .
C00E C 0.5765(4) 0.2535(3) 0.15092(19) 0.0661(7) Uani 1 1 d . . . . .
H00E H 0.713561 0.290891 0.148093 0.079 Uiso 1 1 calc R U . . .
C00F C 0.5386(4) 0.6418(3) 0.2384(2) 0.0693(7) Uani 1 1 d . . . . .
H00A H 0.639329 0.595431 0.201611 0.083 Uiso 1 1 calc R U . . .
H00C H 0.560628 0.612593 0.299747 0.083 Uiso 1 1 calc R U . . .
C00G C 0.1611(5) 0.2661(3) 0.48598(18) 0.0678(7) Uani 1 1 d . . . . .
H00F H 0.006455 0.254200 0.486724 0.081 Uiso 1 1 calc R U . . .
H00G H 0.238795 0.241270 0.543339 0.081 Uiso 1 1 calc R U . . .
C00H C 0.4674(4) 0.1575(3) 0.4180(2) 0.0693(7) Uani 1 1 d . . . . .
H00H H 0.509464 0.104773 0.363529 0.104 Uiso 1 1 calc R U . . .
H00I H 0.498744 0.109584 0.470814 0.104 Uiso 1 1 calc R U . . .
H00J H 0.546682 0.244405 0.431036 0.104 Uiso 1 1 calc R U . . .
C00I C 0.4689(5) 0.1637(3) 0.0758(2) 0.0722(7) Uani 1 1 d . . . . .
H00K H 0.533159 0.140309 0.022464 0.087 Uiso 1 1 calc R U . . .
C00J C 0.2663(5) 0.1091(3) 0.0805(2) 0.0724(7) Uani 1 1 d . . . . .
H00L H 0.194084 0.047868 0.030263 0.087 Uiso 1 1 calc R U . . .
C00K C 0.2637(5) 0.6090(4) 0.0914(2) 0.0840(9) Uani 1 1 d . . . . .
H00M H 0.396269 0.630359 0.067787 0.101 Uiso 1 1 calc R U . . .
H00N H 0.205902 0.520129 0.058787 0.101 Uiso 1 1 calc R U . . .
C00L C 0.0978(5) 0.0411(3) 0.3752(2) 0.0780(8) Uani 1 1 d . . . . .
H00O H -0.054828 0.055515 0.366508 0.117 Uiso 1 1 calc R U . . .
H00P H 0.132254 -0.011582 0.425367 0.117 Uiso 1 1 calc R U . . .
H00Q H 0.135659 -0.007249 0.318408 0.117 Uiso 1 1 calc R U . . .
C00M C 0.5893(7) 0.7937(4) 0.2502(3) 0.1092(13) Uani 1 1 d . . . . .
H00R H 0.567494 0.823537 0.189769 0.164 Uiso 1 1 calc R U . . .
H00S H 0.737519 0.813965 0.278961 0.164 Uiso 1 1 calc R U . . .
H00T H 0.495123 0.840159 0.289217 0.164 Uiso 1 1 calc R U . . .
C00N C 0.1068(7) 0.7109(5) 0.0694(3) 0.1181(14) Uani 1 1 d . . . . .
H00U H 0.077999 0.709248 0.002627 0.177 Uiso 1 1 calc R U . . .
H00V H 0.165178 0.799884 0.099068 0.177 Uiso 1 1 calc R U . . .
H00W H -0.025612 0.690255 0.091995 0.177 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
C00A N004 C00F 124.3(2) . . ?
C00A N004 C00K 117.2(2) . . ?
C00F N004 C00K 117.6(2) . . ?
C006 C005 H005 107.3 . . ?
C006 C005 C00C 103.63(17) . . ?
C007 C005 H005 107.3 . . ?
C007 C005 C006 116.64(18) . . ?
C007 C005 C00C 114.29(18) . . ?
C00C C005 H005 107.3 . . ?
C008 C006 C005 125.6(2) . . ?
C008 C006 C009 125.8(2) . . ?
C009 C006 C005 108.37(19) . . ?
C00B C007 C005 122.25(19) . . ?
C00B C007 C00D 118.2(2) . . ?
C00D C007 C005 119.5(2) . . ?
F001 C008 C00A 112.04(19) . . ?
C006 C008 F001 121.2(2) . . ?
C006 C008 C00A 126.5(2) . . ?
O002 C009 C006 127.1(2) . . ?
O002 C009 C00G 126.3(2) . . ?
C006 C009 C00G 106.55(19) . . ?
O003 C00A N004 123.5(2) . . ?
O003 C00A C008 117.9(2) . . ?
N004 C00A C008 118.51(19) . . ?
C007 C00B H00B 119.5 . . ?
C00E C00B C007 121.0(2) . . ?
C00E C00B H00B 119.5 . . ?
C00G C00C C005 101.88(19) . . ?
C00H C00C C005 112.2(2) . . ?
C00H C00C C00G 109.1(2) . . ?
C00H C00C C00L 110.0(2) . . ?
C00L C00C C005 111.1(2) . . ?
C00L C00C C00G 112.3(2) . . ?
C007 C00D H00D 119.7 . . ?
C00J C00D C007 120.5(2) . . ?
C00J C00D H00D 119.7 . . ?
C00B C00E H00E 119.9 . . ?
C00I C00E C00B 120.1(2) . . ?
C00I C00E H00E 119.9 . . ?
N004 C00F H00A 108.9 . . ?
N004 C00F H00C 108.9 . . ?
N004 C00F C00M 113.3(3) . . ?
H00A C00F H00C 107.7 . . ?
C00M C00F H00A 108.9 . . ?
C00M C00F H00C 108.9 . . ?
C009 C00G C00C 105.3(2) . . ?
C009 C00G H00F 110.7 . . ?
C009 C00G H00G 110.7 . . ?
C00C C00G H00F 110.7 . . ?
C00C C00G H00G 110.7 . . ?
H00F C00G H00G 108.8 . . ?
C00C C00H H00H 109.5 . . ?
C00C C00H H00I 109.5 . . ?
C00C C00H H00J 109.5 . . ?
H00H C00H H00I 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?
C00E C00I H00K 120.2 . . ?
C00J C00I C00E 119.6(2) . . ?
C00J C00I H00K 120.2 . . ?
C00D C00J H00L 119.8 . . ?
C00I C00J C00D 120.5(2) . . ?
C00I C00J H00L 119.8 . . ?
N004 C00K H00M 108.7 . . ?
N004 C00K H00N 108.7 . . ?
H00M C00K H00N 107.6 . . ?
C00N C00K N004 114.1(3) . . ?
C00N C00K H00M 108.7 . . ?
C00N C00K H00N 108.7 . . ?
C00C C00L H00O 109.5 . . ?
C00C C00L H00P 109.5 . . ?
C00C C00L H00Q 109.5 . . ?
H00O C00L H00P 109.5 . . ?
H00O C00L H00Q 109.5 . . ?
H00P C00L H00Q 109.5 . . ?
C00F C00M H00R 109.5 . . ?
C00F C00M H00S 109.5 . . ?
C00F C00M H00T 109.5 . . ?
H00R C00M H00S 109.5 . . ?
H00R C00M H00T 109.5 . . ?
H00S C00M H00T 109.5 . . ?
C00K C00N H00U 109.5 . . ?
C00K C00N H00V 109.5 . . ?
C00K C00N H00W 109.5 . . ?
H00U C00N H00V 109.5 . . ?
H00U C00N H00W 109.5 . . ?
H00V C00N H00W 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
F001 C008 1.358(3) . ?
O002 C009 1.211(3) . ?
O003 C00A 1.225(3) . ?
N004 C00A 1.340(3) . ?
N004 C00F 1.460(3) . ?
N004 C00K 1.477(3) . ?
C005 H005 0.9800 . ?
C005 C006 1.524(3) . ?
C005 C007 1.513(3) . ?
C005 C00C 1.571(3) . ?
C006 C008 1.313(3) . ?
C006 C009 1.495(3) . ?
C007 C00B 1.389(3) . ?
C007 C00D 1.390(3) . ?
C008 C00A 1.505(3) . ?
C009 C00G 1.503(4) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.382(3) . ?
C00C C00G 1.530(4) . ?
C00C C00H 1.520(4) . ?
C00C C00L 1.529(3) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.388(4) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.380(4) . ?
C00F H00A 0.9700 . ?
C00F H00C 0.9700 . ?
C00F C00M 1.508(4) . ?
C00G H00F 0.9700 . ?
C00G H00G 0.9700 . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00I H00K 0.9300 . ?
C00I C00J 1.374(4) . ?
C00J H00L 0.9300 . ?
C00K H00M 0.9700 . ?
C00K H00N 0.9700 . ?
C00K C00N 1.464(5) . ?
C00L H00O 0.9600 . ?
C00L H00P 0.9600 . ?
C00L H00Q 0.9600 . ?
C00M H00R 0.9600 . ?
C00M H00S 0.9600 . ?
C00M H00T 0.9600 . ?
C00N H00U 0.9600 . ?
C00N H00V 0.9600 . ?
C00N H00W 0.9600 . ?
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 C008 C00A O003 -121.6(2) . . . . ?
F001 C008 C00A N004 57.5(3) . . . . ?
O002 C009 C00G C00C -154.5(2) . . . . ?
C005 C006 C008 F001 178.60(19) . . . . ?
C005 C006 C008 C00A 4.7(4) . . . . ?
C005 C006 C009 O002 176.3(2) . . . . ?
C005 C006 C009 C00G -5.6(2) . . . . ?
C005 C007 C00B C00E -179.9(2) . . . . ?
C005 C007 C00D C00J -179.3(2) . . . . ?
C005 C00C C00G C009 -37.6(2) . . . . ?
C006 C005 C007 C00B 34.9(3) . . . . ?
C006 C005 C007 C00D -146.0(2) . . . . ?
C006 C005 C00C C00G 33.4(2) . . . . ?
C006 C005 C00C C00H -83.2(2) . . . . ?
C006 C005 C00C C00L 153.2(2) . . . . ?
C006 C008 C00A O003 52.7(3) . . . . ?
C006 C008 C00A N004 -128.2(3) . . . . ?
C006 C009 C00G C00C 27.5(3) . . . . ?
C007 C005 C006 C008 41.5(3) . . . . ?
C007 C005 C006 C009 -144.14(19) . . . . ?
C007 C005 C00C C00G 161.39(19) . . . . ?
C007 C005 C00C C00H 44.8(3) . . . . ?
C007 C005 C00C C00L -78.8(3) . . . . ?
C007 C00B C00E C00I -1.0(4) . . . . ?
C007 C00D C00J C00I -0.7(4) . . . . ?
C008 C006 C009 O002 -9.3(4) . . . . ?
C008 C006 C009 C00G 168.7(2) . . . . ?
C009 C006 C008 F001 5.2(4) . . . . ?
C009 C006 C008 C00A -168.7(2) . . . . ?
C00A N004 C00F C00M -120.1(3) . . . . ?
C00A N004 C00K C00N 76.7(4) . . . . ?
C00B C007 C00D C00J -0.2(4) . . . . ?
C00B C00E C00I C00J 0.1(4) . . . . ?
C00C C005 C006 C008 168.0(2) . . . . ?
C00C C005 C006 C009 -17.6(2) . . . . ?
C00C C005 C007 C00B -86.1(3) . . . . ?
C00C C005 C007 C00D 92.9(3) . . . . ?
C00D C007 C00B C00E 1.0(4) . . . . ?
C00E C00I C00J C00D 0.7(5) . . . . ?
C00F N004 C00A O003 -169.1(2) . . . . ?
C00F N004 C00A C008 11.9(4) . . . . ?
C00F N004 C00K C00N -113.9(3) . . . . ?
C00H C00C C00G C009 81.2(2) . . . . ?
C00K N004 C00A O003 -0.4(4) . . . . ?
C00K N004 C00A C008 -179.4(2) . . . . ?
C00K N004 C00F C00M 71.3(3) . . . . ?
C00L C00C C00G C009 -156.5(2) . . . . ?
