#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/39/2213958.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213958
loop_
_publ_author_name
'Maria Gdaniec'
_publ_section_title
;
 2,3,4,5,6-Pentafluoroaniline
;
_journal_coeditor_code           SG2169
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2954
_journal_page_last               o2954
_journal_paper_doi               10.1107/S1600536807023197
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C6 H2 F5 N'
_chemical_formula_moiety         'C6 H2 F5 N'
_chemical_formula_sum            'C6 H2 F5 N'
_chemical_formula_weight         183.09
_chemical_melting_point          306
_chemical_name_systematic
;
2,3,4,5,6-Pentafluoroaniline
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.90(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.591(2)
_cell_length_b                   13.311(2)
_cell_length_c                   6.4023(14)
_cell_measurement_reflns_used    1580
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     604.3(2)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_molecular_graphics
;
Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al.,  2006)
;
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.0(3)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       'ω 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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0100
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2423
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         4.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.012
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.168
_refine_ls_extinction_coef       0.023(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   1.083
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         688
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0247
_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)+(0.0435P)²+0.2882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                682
_reflns_number_total             688
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2169.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2213958
_cod_database_fobs_code          2213958
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
N N1 0.4464(3) 0.90222(15) 0.6239(4) 0.0201(5) Uani d 1
F F2 0.70684(17) 0.76715(11) 0.5825(2) 0.0194(3) Uani d 1
F F3 0.6465(2) 0.56639(11) 0.5710(2) 0.0235(4) Uani d 1
F F4 0.3236(2) 0.49224(11) 0.6051(3) 0.0236(4) Uani d 1
F F5 0.06082(18) 0.62247(10) 0.6494(2) 0.0213(3) Uani d 1
F F6 0.1169(2) 0.82310(11) 0.6457(2) 0.0206(3) Uani d 1
C C1 0.4132(3) 0.80038(18) 0.6127(4) 0.0142(5) Uani d 1
C C2 0.5454(3) 0.73180(18) 0.5952(4) 0.0149(4) Uani d 1
C C3 0.5158(3) 0.62946(17) 0.5912(4) 0.0156(5) Uani d 1
C C4 0.3526(3) 0.59154(18) 0.6096(4) 0.0164(5) Uani d 1
C C5 0.2195(3) 0.6579(2) 0.6307(4) 0.0161(5) Uani d 1
C C6 0.2493(3) 0.75991(17) 0.6305(4) 0.0154(5) Uani d 1
H H2 0.341(7) 0.939(3) 0.608(7) 0.047(11) Uiso d 1
H H1 0.522(5) 0.924(3) 0.568(6) 0.025(8) Uiso d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0221(10) 0.0125(10) 0.0274(11) -0.0006(8) 0.0110(10) 0.0010(8)
F2 0.0139(6) 0.0219(7) 0.0240(7) -0.0031(6) 0.0087(6) 0.0001(6)
F3 0.0205(7) 0.0192(7) 0.0333(9) 0.0070(6) 0.0127(6) 0.0011(6)
F4 0.0276(9) 0.0126(7) 0.0329(8) -0.0017(6) 0.0136(7) 0.0000(6)
F5 0.0170(7) 0.0224(7) 0.0275(8) -0.0047(6) 0.0115(6) -0.0005(6)
F6 0.0184(7) 0.0200(7) 0.0260(7) 0.0049(6) 0.0112(6) 0.0005(6)
C1 0.0151(13) 0.0140(10) 0.0128(8) -0.0006(9) 0.0043(9) 0.0003(8)
C2 0.0118(9) 0.0190(12) 0.0135(10) -0.0014(9) 0.0041(8) 0.0009(8)
C3 0.0151(11) 0.0158(11) 0.0160(10) 0.0039(8) 0.0056(9) 0.0001(8)
C4 0.0188(12) 0.0140(10) 0.0151(9) -0.0014(9) 0.0046(9) 0.0004(8)
C5 0.0140(10) 0.0196(11) 0.0146(11) -0.0036(9) 0.0052(8) -0.0004(9)
C6 0.0140(11) 0.0173(11) 0.0146(10) 0.0018(10) 0.0049(8) 0.0012(9)
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 H2 113(3)
C1 N1 H1 118(2)
H2 N1 H1 118(3)
N1 C1 C2 121.8(2)
N1 C1 C6 121.8(2)
C2 C1 C6 116.3(2)
F2 C2 C3 119.4(2)
F2 C2 C1 118.4(2)
C3 C2 C1 122.2(2)
F3 C3 C2 119.9(2)
F3 C3 C4 119.8(2)
C2 C3 C4 120.3(2)
F4 C4 C3 120.3(2)
F4 C4 C5 120.8(2)
C3 C4 C5 118.9(2)
F5 C5 C6 120.1(2)
F5 C5 C4 119.7(2)
C6 C5 C4 120.2(2)
F6 C6 C5 119.4(2)
F6 C6 C1 118.47(19)
C5 C6 C1 122.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.376(3)
N1 H2 0.91(4)
N1 H1 0.83(4)
F2 C2 1.342(3)
F3 C3 1.341(3)
F4 C4 1.339(3)
F5 C5 1.338(3)
F6 C6 1.341(3)
C1 C2 1.390(3)
C1 C6 1.397(3)
C2 C3 1.379(3)
C3 C4 1.381(3)
C4 C5 1.384(3)
C5 C6 1.377(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H2 F3 3_455 0.91(4) 2.20(4) 3.086(3) 162(4)
N1 H1 F4 3 0.83(4) 2.40(4) 3.146(2) 151(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21106528
