#------------------------------------------------------------------------------
#$Date: 2021-11-02 23:57:54 +0100 (Tue 02 de Nov de 2021) $
#$Revision: 270213 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/91/7129184.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_7129184
loop_
_publ_author_name
'Dong, Jinhuan'
'Feng, Wanzhong'
'Wang, Lei'
'Li, Mei'
'Chen, Zhe'
'Xu, Xianxiu'
_publ_section_title
;
 Cu/Base Co-catalyzed [3 + 3] Cycloaddition for the Synthesis of Highly
 Functionalized 4-Fluoropyridines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05412K
_journal_year                    2021
_chemical_formula_moiety         'C14 H11 Cl F N O2'
_chemical_formula_sum            'C14 H11 Cl F N O2'
_chemical_formula_weight         279.69
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2021-04-11 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                103.627(7)
_cell_angle_beta                 97.874(8)
_cell_angle_gamma                98.131(7)
_cell_formula_units_Z            2
_cell_length_a                   7.3135(7)
_cell_length_b                   7.6484(6)
_cell_length_c                   12.3996(11)
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8190
_cell_measurement_theta_min      6.2200
_cell_volume                     656.75(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9868
_diffrn_measured_fraction_theta_max 0.9697
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 -44.00   1.00    1.00    --    0.00 -37.00-150.00   26
  2  ω    -23.00  24.00   1.00    1.00    --    0.00 -37.00-150.00   47
  3  ω      5.00  58.00   1.00    1.00    --    0.00  57.00   0.00   53
  4  ω    -13.00  64.00   1.00    1.00    --   54.00 -57.00-180.00   77
  5  ω     23.00 102.00   1.00    1.00    --   54.00-125.00-180.00   79
  6  ω     72.00  98.00   1.00    1.00    --   54.00  57.00 120.00   26
  7  ω     75.00 100.00   1.00    1.00    --   54.00  57.00-150.00   25
  8  ω    -11.00  79.00   1.00    1.00    --   54.00 -77.00 -60.00   90
  9  ω     76.00 121.00   1.00    1.00    --   54.00  57.00 -30.00   45
 10  ω     28.00 121.00   1.00    1.00    --   54.00  37.00  90.00   93
 11  ω     41.00 129.00   1.00    1.00    --  108.00 -50.00 120.00   88
 12  ω     36.00 109.00   1.00    1.00    --  108.00-111.00 -30.00   73
 13  ω     85.00 151.00   1.00    1.00    --  108.00  37.00-120.00   66
 14  ω     39.00  74.00   1.00    1.00    --  108.00 -91.00 150.00   35
 15  ω    138.00 169.00   1.00    1.00    --  108.00  63.00 -90.00   31
 16  ω     86.00 121.00   1.00    1.00    --  108.00  63.00 -90.00   35
 17  ω     54.00 120.00   1.00    1.00    --  108.00 -77.00 -30.00   66
 18  ω     63.00 133.00   1.00    1.00    --  108.00 -37.00 -30.00   70
 19  ω     36.00 133.00   1.00    1.00    --  108.00 -37.00 -90.00   97
 20  ω     52.00 112.00   1.00    1.00    --  108.00-111.00 120.00   60
 21  ω    142.00 177.00   1.00    1.00    --  108.00  25.00  90.00   35
 22  ω    101.00 127.00   1.00    1.00    --  108.00 111.00 -30.00   26
 23  ω     82.00 143.00   1.00    1.00    --  108.00 -91.00 150.00   61
 24  ω    115.00 171.00   1.00    1.00    --  108.00  37.00 -30.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2082058000
_diffrn_orient_matrix_UB_12      -0.0189862000
_diffrn_orient_matrix_UB_13      0.0171620000
_diffrn_orient_matrix_UB_21      -0.0206459000
_diffrn_orient_matrix_UB_22      -0.0561415000
_diffrn_orient_matrix_UB_23      0.1097753000
_diffrn_orient_matrix_UB_31      -0.0544686000
_diffrn_orient_matrix_UB_32      -0.2022092000
_diffrn_orient_matrix_UB_33      -0.0672836000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3825
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_min         3.73
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0814P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1547
_reflns_number_gt                1864
_reflns_number_total             2312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc05412k2.cif
_cod_data_source_block           exp_3690
_cod_original_cell_volume        656.75(10)
_cod_database_code               7129184
_chemical_oxdiff_formula         'C1 H1 N1 O1 Cl1'
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.670
_oxdiff_exptl_absorpt_empirical_full_min 0.675
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4142(3) 0.3987(3) 0.7589(2) 0.0611(6) Uani 1 1 d . . .
H1 H 0.5147 0.3409 0.7741 0.073 Uiso 1 1 calc R . .
C2 C 0.4128(4) 0.4939(4) 0.6776(2) 0.0672(7) Uani 1 1 d . . .
H2 H 0.5124 0.5020 0.6386 0.081 Uiso 1 1 calc R . .
C3 C 0.2622(4) 0.5771(3) 0.65461(19) 0.0611(6) Uani 1 1 d . . .
C4 C 0.1172(4) 0.5735(3) 0.7139(2) 0.0637(6) Uani 1 1 d . . .
H4 H 0.0183 0.6334 0.6988 0.076 Uiso 1 1 calc R . .
C5 C 0.1205(3) 0.4794(3) 0.7963(2) 0.0592(6) Uani 1 1 d . . .
H5 H 0.0232 0.4774 0.8373 0.071 Uiso 1 1 calc R . .
C6 C 0.2666(3) 0.3876(3) 0.81901(18) 0.0519(5) Uani 1 1 d . . .
C7 C 0.2617(3) 0.2802(3) 0.90350(19) 0.0514(5) Uani 1 1 d . . .
C8 C 0.2853(3) 0.1003(3) 0.88227(19) 0.0564(6) Uani 1 1 d . . .
C9 C 0.2719(3) 0.0008(3) 0.9598(2) 0.0572(6) Uani 1 1 d . . .
H9 H 0.2859 -0.1211 0.9432 0.069 Uiso 1 1 calc R . .
C10 C 0.2367(3) 0.0878(3) 1.06379(19) 0.0517(5) Uani 1 1 d . . .
C11 C 0.2260(4) 0.3522(3) 1.01120(19) 0.0575(6) Uani 1 1 d . . .
H11 H 0.2097 0.4735 1.0293 0.069 Uiso 1 1 calc R . .
C12 C 0.2260(3) -0.0192(3) 1.1499(2) 0.0590(6) Uani 1 1 d . . .
C13 C 0.2048(7) -0.0147(4) 1.3394(3) 0.1024(12) Uani 1 1 d . . .
H13A H 0.0905 -0.1045 1.3248 0.123 Uiso 1 1 calc R . .
H13B H 0.3106 -0.0779 1.3425 0.123 Uiso 1 1 calc R . .
C14 C 0.2172(6) 0.1161(5) 1.4439(3) 0.1044(12) Uani 1 1 d . . .
H14A H 0.3234 0.2116 1.4542 0.157 Uiso 1 1 calc R . .
H14B H 0.2318 0.0575 1.5043 0.157 Uiso 1 1 calc R . .
H14C H 0.1047 0.1674 1.4438 0.157 Uiso 1 1 calc R . .
Cl1 Cl 0.25497(13) 0.68525(11) 0.54539(6) 0.0911(4) Uani 1 1 d . . .
N1 N 0.2133(3) 0.2623(2) 1.09026(16) 0.0579(5) Uani 1 1 d . . .
O1 O 0.2377(3) -0.1786(2) 1.13029(17) 0.0782(6) Uani 1 1 d . . .
O2 O 0.2046(3) 0.0784(2) 1.24868(15) 0.0768(6) Uani 1 1 d . . .
F1 F 0.3180(3) 0.01702(19) 0.77951(13) 0.0827(5) 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 0.0181 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'
Cl Cl 0.3639 0.7018 '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 C1 H1 119.5 . . ?
C2 C1 C6 120.9(2) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 Cl1 118.8(2) . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 Cl1 119.6(2) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 121.8(2) . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 C7 120.1(2) . . ?
C8 C7 C6 123.5(2) . . ?
C8 C7 C11 114.4(2) . . ?
C11 C7 C6 122.12(19) . . ?
C9 C8 C7 122.6(2) . . ?
F1 C8 C7 118.9(2) . . ?
F1 C8 C9 118.45(19) . . ?
C8 C9 H9 121.2 . . ?
C8 C9 C10 117.56(19) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 C12 117.80(19) . . ?
N1 C10 C9 122.9(2) . . ?
N1 C10 C12 119.3(2) . . ?
C7 C11 H11 117.2 . . ?
N1 C11 C7 125.5(2) . . ?
N1 C11 H11 117.2 . . ?
O1 C12 C10 122.8(2) . . ?
O1 C12 O2 123.8(2) . . ?
O2 C12 C10 113.42(19) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C14 C13 O2 109.4(2) . . ?
O2 C13 H13A 109.8 . . ?
O2 C13 H13B 109.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 N1 C10 116.98(19) . . ?
C12 O2 C13 116.5(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
C1 H1 0.9300 . ?
C1 C2 1.376(4) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 C4 1.371(4) . ?
C3 Cl1 1.744(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C6 C7 1.477(3) . ?
C7 C8 1.379(3) . ?
C7 C11 1.394(3) . ?
C8 C9 1.365(3) . ?
C8 F1 1.353(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 C12 1.494(3) . ?
C10 N1 1.339(3) . ?
C11 H11 0.9300 . ?
C11 N1 1.329(3) . ?
C12 O1 1.203(3) . ?
C12 O2 1.319(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.421(4) . ?
C13 O2 1.466(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C1 C2 C3 C4 2.6(4) . . . . ?
C1 C2 C3 Cl1 -176.05(18) . . . . ?
C1 C6 C7 C8 -51.2(3) . . . . ?
C1 C6 C7 C11 131.0(2) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C7 177.6(2) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 2.3(3) . . . . ?
C4 C5 C6 C7 -176.8(2) . . . . ?
C5 C6 C7 C8 127.9(2) . . . . ?
C5 C6 C7 C11 -49.9(3) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C6 C7 C8 C9 -177.0(2) . . . . ?
C6 C7 C8 F1 1.1(3) . . . . ?
C6 C7 C11 N1 177.7(2) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
C7 C11 N1 C10 0.0(4) . . . . ?
C8 C7 C11 N1 -0.3(4) . . . . ?
C8 C9 C10 C12 -178.7(2) . . . . ?
C8 C9 C10 N1 0.9(3) . . . . ?
C9 C10 C12 O1 -3.6(4) . . . . ?
C9 C10 C12 O2 175.7(2) . . . . ?
C9 C10 N1 C11 -0.3(3) . . . . ?
C10 C12 O2 C13 -176.3(3) . . . . ?
C11 C7 C8 C9 1.0(3) . . . . ?
C11 C7 C8 F1 179.1(2) . . . . ?
C12 C10 N1 C11 179.3(2) . . . . ?
C14 C13 O2 C12 168.8(3) . . . . ?
Cl1 C3 C4 C5 176.78(18) . . . . ?
N1 C10 C12 O1 176.7(2) . . . . ?
N1 C10 C12 O2 -3.9(3) . . . . ?
O1 C12 O2 C13 3.0(4) . . . . ?
F1 C8 C9 C10 -179.4(2) . . . . ?
