#------------------------------------------------------------------------------
#$Date: 2024-09-06 01:14:24 +0200 (Fri 06 de Sep de 2024) $
#$Revision: 294427 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/34/7133439.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_7133439
loop_
_publ_author_name
'Zhou, Honggui'
'Li, Zhefeng'
'Chen, Juehong'
'Zhou, Si'
'Wang, Xinyu'
'Zhang, Linwei'
'Chen, Jiuxi'
'Lv, Ningning'
_publ_section_title
;
 Synthesis of polysubstituted pyridazines via Cu-mediated
 C(sp³)-C(sp³) coupling/annulation of saturated
 ketones with acylhydrazones.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9546
_journal_page_last               9549
_journal_paper_doi               10.1039/d4cc02760d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C22 H15 F N2'
_chemical_formula_weight         326.36
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2drs76
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-12-19 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                103.314(11)
_cell_angle_beta                 100.861(12)
_cell_angle_gamma                113.664(11)
_cell_formula_units_Z            2
_cell_length_a                   8.757(4)
_cell_length_b                   9.973(4)
_cell_length_c                   11.506(4)
_cell_measurement_reflns_used    5264
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.211
_cell_measurement_theta_min      4.982
_cell_volume                     850.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11393
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.371
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.062(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0673
_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)+(0.1030P)²+0.2391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2170
_reflns_number_total             3083
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02760d2.cif
_cod_data_source_block           mo_dd22115_0m
_cod_depositor_comments          'Adding full bibliography for 7133439.cif.'
_cod_original_cell_volume        850.1(6)
_cod_database_code               7133439
_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_min   0.984
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
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 0.9593(2) 0.86022(17) 1.05594(15) 0.0720(5) Uani 1 1 d . . . . .
N1 N 0.2112(3) 0.1651(2) 0.47866(19) 0.0486(6) Uani 1 1 d . . . . .
N2 N 0.2798(3) 0.0987(2) 0.40347(19) 0.0493(6) Uani 1 1 d . . . . .
C1 C 0.3157(3) 0.2914(3) 0.5818(2) 0.0436(6) Uani 1 1 d . . . . .
C2 C 0.4997(3) 0.3577(3) 0.6157(2) 0.0430(6) Uani 1 1 d . . . . .
C3 C 0.5677(3) 0.2914(3) 0.5346(2) 0.0478(6) Uani 1 1 d . . . . .
H3 H 0.6899 0.3335 0.5509 0.057 Uiso 1 1 calc R U . . .
C4 C 0.4536(3) 0.1611(3) 0.4280(2) 0.0452(6) Uani 1 1 d . . . . .
C5 C 0.5181(3) 0.0839(3) 0.3369(2) 0.0467(6) Uani 1 1 d . . . . .
C6 C 0.6830(4) 0.0934(3) 0.3728(3) 0.0556(7) Uani 1 1 d . . . . .
H6 H 0.7551 0.1482 0.4569 0.067 Uiso 1 1 calc R U . . .
C7 C 0.7440(4) 0.0234(3) 0.2871(3) 0.0626(8) Uani 1 1 d . . . . .
H7 H 0.8568 0.0314 0.3127 0.075 Uiso 1 1 calc R U . . .
C8 C 0.6375(5) -0.0581(3) 0.1639(3) 0.0669(9) Uani 1 1 d . . . . .
H8 H 0.6776 -0.1062 0.1053 0.080 Uiso 1 1 calc R U . . .
C9 C 0.4724(5) -0.0693(3) 0.1263(3) 0.0673(9) Uani 1 1 d . . . . .
H9 H 0.4005 -0.1253 0.0422 0.081 Uiso 1 1 calc R U . . .
C10 C 0.4118(4) 0.0017(3) 0.2120(2) 0.0558(7) Uani 1 1 d . . . . .
H10 H 0.2994 -0.0058 0.1859 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2190(3) 0.3548(3) 0.6522(2) 0.0448(6) Uani 1 1 d . . . . .
C12 C 0.0682(3) 0.2544(3) 0.6698(2) 0.0474(6) Uani 1 1 d . . . . .
H12 H 0.0268 0.1463 0.6368 0.057 Uiso 1 1 calc R U . . .
C13 C -0.0216(4) 0.3115(3) 0.7351(2) 0.0546(7) Uani 1 1 d . . . . .
H13 H -0.1229 0.2423 0.7472 0.065 Uiso 1 1 calc R U . . .
C14 C 0.0365(4) 0.4709(3) 0.7832(3) 0.0584(7) Uani 1 1 d . . . . .
H14 H -0.0245 0.5096 0.8284 0.070 Uiso 1 1 calc R U . . .
C15 C 0.1840(4) 0.5718(3) 0.7640(3) 0.0596(8) Uani 1 1 d . . . . .
H15 H 0.2225 0.6795 0.7947 0.071 Uiso 1 1 calc R U . . .
C16 C 0.2760(4) 0.5147(3) 0.6995(2) 0.0525(7) Uani 1 1 d . . . . .
H16 H 0.3774 0.5842 0.6876 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6208(3) 0.4916(3) 0.7330(2) 0.0437(6) Uani 1 1 d . . . . .
C18 C 0.6127(3) 0.4822(3) 0.8504(2) 0.0499(6) Uani 1 1 d . . . . .
H18 H 0.5286 0.3907 0.8559 0.060 Uiso 1 1 calc R U . . .
C19 C 0.7267(4) 0.6055(3) 0.9596(2) 0.0536(7) Uani 1 1 d . . . . .
H19 H 0.7221 0.5989 1.0392 0.064 Uiso 1 1 calc R U . . .
C20 C 0.8467(4) 0.7376(3) 0.9478(2) 0.0524(7) Uani 1 1 d . . . . .
C21 C 0.8604(4) 0.7524(3) 0.8350(3) 0.0543(7) Uani 1 1 d . . . . .
H21 H 0.9441 0.8450 0.8307 0.065 Uiso 1 1 calc R U . . .
C22 C 0.7471(3) 0.6267(3) 0.7266(2) 0.0502(7) Uani 1 1 d . . . . .
H22 H 0.7562 0.6332 0.6477 0.060 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 0.0033 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'
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
N2 N1 C1 120.8(2) . . ?
C4 N2 N1 120.0(2) . . ?
N1 C1 C2 121.6(2) . . ?
N1 C1 C11 114.1(2) . . ?
C2 C1 C11 124.2(2) . . ?
C3 C2 C1 116.6(2) . . ?
C3 C2 C17 119.8(2) . . ?
C1 C2 C17 123.6(2) . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
N2 C4 C3 121.2(2) . . ?
N2 C4 C5 116.5(2) . . ?
C3 C4 C5 122.2(2) . . ?
C6 C5 C10 118.9(2) . . ?
C6 C5 C4 121.4(2) . . ?
C10 C5 C4 119.6(2) . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
C12 C11 C16 118.8(2) . . ?
C12 C11 C1 120.1(2) . . ?
C16 C11 C1 121.2(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C22 C17 C18 118.8(2) . . ?
C22 C17 C2 120.3(2) . . ?
C18 C17 C2 120.8(2) . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 117.8(2) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C21 C20 F1 118.7(2) . . ?
C21 C20 C19 123.5(2) . . ?
F1 C20 C19 117.8(2) . . ?
C20 C21 C22 118.0(2) . . ?
C20 C21 H21 121.0 . . ?
C22 C21 H21 121.0 . . ?
C17 C22 C21 120.9(2) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
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 C20 1.373(3) . ?
N1 N2 1.342(3) . ?
N1 C1 1.345(3) . ?
N2 C4 1.334(3) . ?
C1 C2 1.406(3) . ?
C1 C11 1.492(3) . ?
C2 C3 1.380(3) . ?
C2 C17 1.491(3) . ?
C3 C4 1.398(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.487(3) . ?
C5 C6 1.383(4) . ?
C5 C10 1.394(3) . ?
C6 C7 1.388(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.379(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.386(3) . ?
C11 C16 1.396(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.385(4) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 C22 1.387(3) . ?
C17 C18 1.389(3) . ?
C18 C19 1.385(3) . ?
C18 H18 0.9400 . ?
C19 C20 1.373(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.361(4) . ?
C21 C22 1.388(3) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H21 F1 0.94 2.62 3.334(3) 132.8 2_777
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 N1 N2 C4 -2.4(3) . . . . ?
N2 N1 C1 C2 -0.7(3) . . . . ?
N2 N1 C1 C11 177.58(19) . . . . ?
N1 C1 C2 C3 3.1(3) . . . . ?
C11 C1 C2 C3 -175.0(2) . . . . ?
N1 C1 C2 C17 -176.2(2) . . . . ?
C11 C1 C2 C17 5.7(4) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C17 C2 C3 C4 176.9(2) . . . . ?
N1 N2 C4 C3 3.1(3) . . . . ?
N1 N2 C4 C5 -177.5(2) . . . . ?
C2 C3 C4 N2 -0.5(4) . . . . ?
C2 C3 C4 C5 -179.9(2) . . . . ?
N2 C4 C5 C6 -153.8(2) . . . . ?
C3 C4 C5 C6 25.7(3) . . . . ?
N2 C4 C5 C10 27.0(3) . . . . ?
C3 C4 C5 C10 -153.6(2) . . . . ?
C10 C5 C6 C7 0.3(4) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C6 C5 C10 C9 0.1(4) . . . . ?
C4 C5 C10 C9 179.4(2) . . . . ?
N1 C1 C11 C12 41.6(3) . . . . ?
C2 C1 C11 C12 -140.1(2) . . . . ?
N1 C1 C11 C16 -137.3(2) . . . . ?
C2 C1 C11 C16 41.0(4) . . . . ?
C16 C11 C12 C13 -1.4(4) . . . . ?
C1 C11 C12 C13 179.7(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C14 C15 C16 C11 0.7(4) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
C1 C11 C16 C15 179.6(2) . . . . ?
C3 C2 C17 C22 57.5(3) . . . . ?
C1 C2 C17 C22 -123.1(3) . . . . ?
C3 C2 C17 C18 -120.6(3) . . . . ?
C1 C2 C17 C18 58.7(3) . . . . ?
C22 C17 C18 C19 0.8(4) . . . . ?
C2 C17 C18 C19 179.0(2) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 C21 -0.9(4) . . . . ?
C18 C19 C20 F1 179.7(2) . . . . ?
F1 C20 C21 C22 179.2(2) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C18 C17 C22 C21 -1.9(4) . . . . ?
C2 C17 C22 C21 179.9(2) . . . . ?
C20 C21 C22 C17 1.7(4) . . . . ?
