#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/1/50/49/1504984.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_1504984
loop_
_publ_author_name
'Lu, Changqing'
'VanDerveer, Don'
'DesMarteau, Darryl D.'
_publ_section_title
;
 Fluoroalkylation of imidazoles by hypervalent iodonium salts.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5565
_journal_page_last               5568
_journal_paper_doi               10.1021/ol802399z
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C6 H3 F7 N2'
_chemical_formula_weight         236.10
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.823(2)
_cell_length_b                   7.3020(15)
_cell_length_c                   23.688(5)
_cell_measurement_reflns_used    349
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      24.3606
_cell_measurement_theta_min      5.2910
_cell_volume                     1699.1(6)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC,2001)'
_computing_data_collection       'CrystalClear (Rigaku/MSC,2001)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC,2001)'
_computing_molecular_graphics    'SHELXTL 6.10 (Bruker AXS,2000)'
_computing_publication_material  'SHELXTL 6.10 (Bruker AXS,2000)'
_computing_structure_refinement  'SHELXTL 6.10 (Bruker AXS,2000)'
_computing_structure_solution    'SHELXTL 6.10 (Bruker AXS,2000)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
scan:
    Number of images: 260
               Slice: -40.0000 - 90.0000
         Image width: 0.5000
            Exp time: 240.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 27.6492
              2theta: -0.2503
scan:
    Number of images: 220
               Slice: -30.0000 - 80.0000
         Image width: 0.5000
            Exp time: 240.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 27.6492
              2theta: -0.2503

;
_diffrn_measurement_device
;
Mercury CCD (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3 circle
;
_diffrn_measurement_method       omega
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2379
_diffrn_reflns_av_sigmaI/netI    0.1623
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4163
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.8568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'REQAB, Rigaku/MSC, The Woodlands, TX, USA, 1999'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.447
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.447
_refine_ls_R_factor_all          0.2384
_refine_ls_R_factor_gt           0.1748
_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/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4132
_refine_ls_wR_factor_ref         0.4888
_reflns_number_gt                744
_reflns_number_total             1462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802399z_si_003.cif
_cod_data_source_block           imidazole
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1504984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
F1 F 0.2563(7) 0.2607(11) 0.1721(3) 0.079(2) Uani 1 1 d .
F2 F 0.3998(9) 0.3790(14) 0.2279(3) 0.087(3) Uani 1 1 d .
F3 F 0.3630(8) 0.0903(14) 0.2299(3) 0.082(3) Uani 1 1 d .
F4 F 0.4382(8) 0.0703(10) 0.1181(3) 0.076(2) Uani 1 1 d .
F5 F 0.5974(8) 0.1394(15) 0.1801(3) 0.086(3) Uani 1 1 d .
F6 F 0.4154(7) 0.4468(11) 0.0962(3) 0.072(2) Uani 1 1 d .
F7 F 0.5885(8) 0.4904(11) 0.1523(3) 0.074(2) Uani 1 1 d .
N1 N 0.8039(9) 0.2694(14) 0.0172(4) 0.054(2) Uani 1 1 d .
H1N H 0.8919 0.2599 0.0042 0.064 Uiso 1 1 calc R
N2 N 0.5782(9) 0.2606(14) 0.0191(4) 0.055(2) Uani 1 1 d .
C1 C 0.6881(11) 0.2288(17) -0.0123(5) 0.055(3) Uani 1 1 d .
H1 H 0.6863 0.1836 -0.0503 0.066 Uiso 1 1 calc R
C2 C 0.6255(10) 0.3213(17) 0.0695(4) 0.050(3) Uani 1 1 d .
C3 C 0.7640(10) 0.3274(19) 0.0703(5) 0.059(3) Uani 1 1 d .
H3 H 0.8215 0.3640 0.1010 0.070 Uiso 1 1 calc R
C4 C 0.5313(11) 0.3673(15) 0.1171(4) 0.050(2) Uani 1 1 d .
C5 C 0.4873(10) 0.2041(17) 0.1537(5) 0.055(3) Uani 1 1 d .
C6 C 0.3743(11) 0.232(2) 0.1972(5) 0.064(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.040(4) 0.105(6) 0.094(5) 0.005(4) 0.001(3) 0.003(4)
F2 0.070(5) 0.108(7) 0.082(5) -0.035(5) 0.022(4) -0.023(5)
F3 0.066(5) 0.109(6) 0.070(4) 0.019(5) 0.016(3) -0.012(5)
F4 0.068(4) 0.067(4) 0.093(5) -0.001(4) 0.029(4) -0.014(4)
F5 0.053(4) 0.126(7) 0.080(5) 0.030(5) 0.006(3) 0.024(5)
F6 0.048(3) 0.080(5) 0.087(5) 0.010(4) 0.010(3) 0.020(3)
F7 0.070(4) 0.077(5) 0.076(4) -0.014(4) 0.017(3) -0.018(4)
N1 0.029(4) 0.074(7) 0.058(5) 0.008(4) -0.006(4) -0.001(4)
N2 0.031(4) 0.070(6) 0.063(5) 0.002(5) 0.003(4) -0.004(4)
C1 0.037(5) 0.066(8) 0.063(6) 0.015(5) 0.004(5) 0.006(5)
C2 0.035(5) 0.068(7) 0.048(5) -0.006(5) 0.005(4) -0.007(5)
C3 0.031(5) 0.084(8) 0.061(6) 0.006(6) -0.008(4) -0.015(5)
C4 0.048(5) 0.050(5) 0.051(5) -0.005(5) 0.006(4) 0.000(5)
C5 0.035(5) 0.059(6) 0.071(6) 0.009(6) 0.003(5) 0.007(5)
C6 0.043(6) 0.089(9) 0.060(6) 0.006(7) 0.007(5) -0.013(6)
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
C1 N1 C3 107.1(9)
C1 N1 H1N 126.4
C3 N1 H1N 126.4
C1 N2 C2 105.7(9)
N2 C1 N1 110.6(10)
N2 C1 H1 124.7
N1 C1 H1 124.7
N2 C2 C3 111.4(10)
N2 C2 C4 121.7(9)
C3 C2 C4 126.9(10)
C2 C3 N1 105.2(9)
C2 C3 H3 127.4
N1 C3 H3 127.4
F7 C4 F6 106.6(9)
F7 C4 C2 110.9(9)
F6 C4 C2 109.7(9)
F7 C4 C5 106.6(9)
F6 C4 C5 107.4(8)
C2 C4 C5 115.2(9)
F5 C5 F4 108.6(10)
F5 C5 C6 108.7(10)
F4 C5 C6 104.7(9)
F5 C5 C4 108.1(9)
F4 C5 C4 107.7(9)
C6 C5 C4 118.7(10)
F3 C6 F2 109.7(10)
F3 C6 F1 108.6(10)
F2 C6 F1 106.8(12)
F3 C6 C5 110.9(11)
F2 C6 C5 110.0(10)
F1 C6 C5 110.8(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C6 1.320(14)
F2 C6 1.318(16)
F3 C6 1.299(16)
F4 C5 1.378(15)
F5 C5 1.336(13)
F6 C4 1.370(13)
F7 C4 1.349(13)
N1 C1 1.368(15)
N1 C3 1.382(16)
N1 H1N 0.9200
N2 C1 1.330(15)
N2 C2 1.355(14)
C1 H1 0.9600
C2 C3 1.361(15)
C2 C4 1.497(14)
C3 H3 0.9600
C4 C5 1.535(16)
C5 C6 1.529(15)
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
C2 N2 C1 N1 -0.4(13)
C3 N1 C1 N2 0.9(13)
C1 N2 C2 C3 -0.3(14)
C1 N2 C2 C4 -178.3(11)
N2 C2 C3 N1 0.8(15)
C4 C2 C3 N1 178.7(11)
C1 N1 C3 C2 -1.0(13)
N2 C2 C4 F7 -154.5(11)
C3 C2 C4 F7 27.7(17)
N2 C2 C4 F6 -37.0(15)
C3 C2 C4 F6 145.3(13)
N2 C2 C4 C5 84.3(14)
C3 C2 C4 C5 -93.4(15)
F7 C4 C5 F5 -58.2(12)
F6 C4 C5 F5 -172.2(9)
C2 C4 C5 F5 65.3(13)
F7 C4 C5 F4 -175.4(9)
F6 C4 C5 F4 70.6(10)
C2 C4 C5 F4 -51.9(11)
F7 C4 C5 C6 66.1(12)
F6 C4 C5 C6 -47.9(13)
C2 C4 C5 C6 -170.5(10)
F5 C5 C6 F3 -46.8(14)
F4 C5 C6 F3 69.1(11)
C4 C5 C6 F3 -170.8(10)
F5 C5 C6 F2 74.7(14)
F4 C5 C6 F2 -169.4(10)
C4 C5 C6 F2 -49.3(14)
F5 C5 C6 F1 -167.4(11)
F4 C5 C6 F1 -51.5(13)
C4 C5 C6 F1 68.6(15)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 500926 ChemSpider
2 576202 PubChem
