#------------------------------------------------------------------------------
#$Date: 2022-07-23 05:30:49 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276875 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158789.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_7158789
loop_
_publ_author_name
'Geng, Furong'
'Wu, Shaofeng'
'Gan, Xinyang'
'Hou, Wenjuan'
'Dong, Jianyu'
'Zhou, Yongbo'
_publ_section_title
;
 TEMPO mediated oxidative annulation of aryl methyl ketones with
 amines/ammonium acetate for imidazole synthesis.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5416
_journal_page_last               5422
_journal_paper_doi               10.1039/d2ob00828a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_sum            'C24 H16 F6 N2'
_chemical_formula_weight         446.39
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-12-16 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                106.776(4)
_cell_angle_beta                 99.113(4)
_cell_angle_gamma                96.569(6)
_cell_formula_units_Z            2
_cell_length_a                   7.6201(11)
_cell_length_b                   11.120(2)
_cell_length_c                   12.625(2)
_cell_measurement_reflns_used    3488
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.15
_cell_volume                     996.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12636
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.4702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                3298
_reflns_number_total             3488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob00828a2.cif
_cod_data_source_block           wsf
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7158789
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F4 F 0.12882(12) -0.06454(8) 0.07468(8) 0.0407(2) Uani 1 1 d . . .
F5 F 0.26795(14) -0.04078(9) 0.24325(8) 0.0443(3) Uani 1 1 d . . .
N1 N 0.78370(14) 0.40629(10) 0.02129(9) 0.0212(2) Uani 1 1 d . . .
N2 N 0.75125(14) 0.56382(10) -0.05213(9) 0.0223(2) Uani 1 1 d . . .
C6 C 0.67148(17) 0.57994(13) 0.23109(11) 0.0236(3) Uani 1 1 d . . .
H6 H 0.6229 0.4946 0.2157 0.028 Uiso 1 1 calc R . .
F1 F 0.59726(15) 0.85534(10) 0.51361(9) 0.0579(3) Uani 1 1 d . . .
C18 C 0.66993(18) 0.25335(12) 0.11723(11) 0.0226(3) Uani 1 1 d . . .
F6 F 0.10795(14) 0.09652(9) 0.21189(10) 0.0541(3) Uani 1 1 d . . .
C17 C 0.82833(18) 0.33935(13) 0.10375(11) 0.0235(3) Uani 1 1 d . . .
H17A H 0.8808 0.4021 0.1766 0.028 Uiso 1 1 calc R . .
H17B H 0.9192 0.2884 0.0813 0.028 Uiso 1 1 calc R . .
C8 C 0.75950(16) 0.53083(12) 0.04088(11) 0.0210(3) Uani 1 1 d . . .
F2 F 0.88334(15) 0.89475(12) 0.54504(8) 0.0594(3) Uani 1 1 d . . .
C9 C 0.79005(17) 0.35971(12) -0.09119(11) 0.0225(3) Uani 1 1 d . . .
H9 H 0.8051 0.2778 -0.1296 0.027 Uiso 1 1 calc R . .
C4 C 0.81810(18) 0.74832(13) 0.17515(11) 0.0241(3) Uani 1 1 d . . .
H4 H 0.8684 0.7758 0.1219 0.029 Uiso 1 1 calc R . .
C7 C 0.66547(18) 0.66740(13) 0.33322(11) 0.0253(3) Uani 1 1 d . . .
H7 H 0.6141 0.6405 0.3864 0.030 Uiso 1 1 calc R . .
C3 C 0.81169(18) 0.83585(13) 0.27661(12) 0.0267(3) Uani 1 1 d . . .
H3 H 0.8577 0.9215 0.2917 0.032 Uiso 1 1 calc R . .
C10 C 0.77004(16) 0.45704(12) -0.13569(11) 0.0212(3) Uani 1 1 d . . .
C21 C 0.38451(19) 0.09809(12) 0.15043(12) 0.0257(3) Uani 1 1 d . . .
F3 F 0.73223(19) 1.00581(10) 0.46637(9) 0.0623(3) Uani 1 1 d . . .
C19 C 0.51336(19) 0.20784(13) 0.03559(12) 0.0272(3) Uani 1 1 d . . .
H19 H 0.5035 0.2294 -0.0307 0.033 Uiso 1 1 calc R . .
C2 C 0.73578(18) 0.79503(13) 0.35655(11) 0.0256(3) Uani 1 1 d . . .
C11 C 0.77002(17) 0.45831(13) -0.25181(11) 0.0226(3) Uani 1 1 d . . .
C5 C 0.75012(17) 0.61882(12) 0.15090(11) 0.0217(3) Uani 1 1 d . . .
C12 C 0.73542(19) 0.56569(13) -0.28232(12) 0.0283(3) Uani 1 1 d . . .
H12 H 0.7108 0.6359 -0.2292 0.034 Uiso 1 1 calc R . .
C22 C 0.5420(2) 0.14143(14) 0.23242(12) 0.0337(3) Uani 1 1 d . . .
H22 H 0.5520 0.1190 0.2983 0.040 Uiso 1 1 calc R . .
C16 C 0.80599(19) 0.35423(14) -0.33338(12) 0.0286(3) Uani 1 1 d . . .
H16 H 0.8291 0.2818 -0.3146 0.034 Uiso 1 1 calc R . .
C20 C 0.37104(19) 0.13027(13) 0.05196(12) 0.0286(3) Uani 1 1 d . . .
H20 H 0.2664 0.0998 -0.0034 0.034 Uiso 1 1 calc R . .
C23 C 0.6836(2) 0.21823(14) 0.21517(12) 0.0317(3) Uani 1 1 d . . .
H23 H 0.7894 0.2468 0.2697 0.038 Uiso 1 1 calc R . .
C1 C 0.7353(2) 0.88746(15) 0.46893(13) 0.0341(3) Uani 1 1 d . . .
C24 C 0.2247(2) 0.02306(13) 0.17037(13) 0.0324(3) Uani 1 1 d . . .
C15 C 0.8076(2) 0.35764(16) -0.44219(13) 0.0368(4) Uani 1 1 d . . .
H15 H 0.8316 0.2876 -0.4958 0.044 Uiso 1 1 calc R . .
C13 C 0.7375(2) 0.56854(15) -0.39112(13) 0.0374(4) Uani 1 1 d . . .
H13 H 0.7143 0.6406 -0.4105 0.045 Uiso 1 1 calc R . .
C14 C 0.7738(2) 0.46480(17) -0.47132(13) 0.0403(4) Uani 1 1 d . . .
H14 H 0.7754 0.4672 -0.5442 0.048 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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 '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
C8 N1 C9 106.45(11) . . ?
C8 N1 C17 128.43(11) . . ?
C9 N1 C17 124.23(11) . . ?
C8 N2 C10 106.06(11) . . ?
C7 C6 C5 120.52(12) . . ?
C19 C18 C23 118.98(13) . . ?
C19 C18 C17 122.44(12) . . ?
C23 C18 C17 118.59(12) . . ?
N1 C17 C18 114.67(11) . . ?
N2 C8 N1 111.24(11) . . ?
N2 C8 C5 123.55(12) . . ?
N1 C8 C5 125.18(11) . . ?
C10 C9 N1 106.82(11) . . ?
C3 C4 C5 121.11(12) . . ?
C6 C7 C2 120.19(13) . . ?
C4 C3 C2 119.59(13) . . ?
C9 C10 N2 109.43(11) . . ?
C9 C10 C11 128.93(12) . . ?
N2 C10 C11 121.63(12) . . ?
C20 C21 C22 120.08(13) . . ?
C20 C21 C24 119.25(13) . . ?
C22 C21 C24 120.57(13) . . ?
C18 C19 C20 120.47(13) . . ?
C7 C2 C3 120.03(13) . . ?
C7 C2 C1 119.62(13) . . ?
C3 C2 C1 120.32(13) . . ?
C16 C11 C12 118.50(13) . . ?
C16 C11 C10 121.45(12) . . ?
C12 C11 C10 120.04(12) . . ?
C6 C5 C4 118.53(12) . . ?
C6 C5 C8 123.07(12) . . ?
C4 C5 C8 118.37(12) . . ?
C13 C12 C11 120.51(13) . . ?
C23 C22 C21 119.43(13) . . ?
C15 C16 C11 120.70(14) . . ?
C21 C20 C19 120.11(13) . . ?
C22 C23 C18 120.91(14) . . ?
F3 C1 F1 107.34(13) . . ?
F3 C1 F2 105.50(13) . . ?
F1 C1 F2 105.38(13) . . ?
F3 C1 C2 113.34(13) . . ?
F1 C1 C2 112.99(12) . . ?
F2 C1 C2 111.69(13) . . ?
F5 C24 F6 106.19(12) . . ?
F5 C24 F4 106.15(11) . . ?
F6 C24 F4 105.61(13) . . ?
F5 C24 C21 113.36(13) . . ?
F6 C24 C21 112.49(12) . . ?
F4 C24 C21 112.44(12) . . ?
C14 C15 C16 120.27(14) . . ?
C12 C13 C14 120.49(14) . . ?
C15 C14 C13 119.52(14) . . ?
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
F4 C24 1.3492(18) . ?
F5 C24 1.3392(18) . ?
N1 C8 1.3742(17) . ?
N1 C9 1.3747(17) . ?
N1 C17 1.4652(16) . ?
N2 C8 1.3221(17) . ?
N2 C10 1.3809(17) . ?
C6 C7 1.3840(19) . ?
C6 C5 1.3988(19) . ?
F1 C1 1.3307(18) . ?
C18 C19 1.3831(19) . ?
C18 C23 1.3927(19) . ?
C18 C17 1.5150(18) . ?
F6 C24 1.3418(18) . ?
C8 C5 1.4678(18) . ?
F2 C1 1.3390(19) . ?
C9 C10 1.3682(19) . ?
C4 C3 1.379(2) . ?
C4 C5 1.4002(19) . ?
C7 C2 1.387(2) . ?
C3 C2 1.396(2) . ?
C10 C11 1.4701(18) . ?
C21 C20 1.382(2) . ?
C21 C22 1.389(2) . ?
C21 C24 1.493(2) . ?
F3 C1 1.3286(19) . ?
C19 C20 1.387(2) . ?
C2 C1 1.493(2) . ?
C11 C16 1.396(2) . ?
C11 C12 1.396(2) . ?
C12 C13 1.386(2) . ?
C22 C23 1.383(2) . ?
C16 C15 1.387(2) . ?
C15 C14 1.384(2) . ?
C13 C14 1.386(2) . ?
