#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/15/2231582.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_2231582
loop_
_publ_author_name
'Cao, Wanwan'
'Zhong, Jun-wen'
'Wang, Jin'
'Liu, Pei-lian'
'Zeng, Zhuo'
_publ_section_title
;
 2-(3,3,4,4-Tetrafluoropyrrolidin-1-yl)aniline
;
_journal_coeditor_code           LD2018
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2220
_journal_paper_doi               10.1107/S1600536811030339
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H10 F4 N2'
_chemical_formula_moiety         'C10 H10 F4 N2'
_chemical_formula_sum            'C10 H10 F4 N2'
_chemical_formula_weight         234.20
_chemical_name_systematic
;
2-(3,3,4,4-Tetrafluoropyrrolidin-1-yl)aniline
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.791(13)
_cell_length_b                   8.185(16)
_cell_length_c                   18.66(4)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.99
_cell_volume                     1037(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELTLX (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6022
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.9696
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0405
_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)+(0.0380P)²+0.0935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                748
_reflns_number_total             1342
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ld2018.cif
_cod_data_source_block           I
_cod_original_cell_volume        1037(3)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               2231582
_cod_database_fobs_code          2231582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
F F2 0.5502(4) 0.9533(4) 0.28755(12) 0.0946(9) Uani d . 1 1
F F4 0.9856(4) 0.9465(4) 0.22927(13) 0.0938(9) Uani d . 1 1
F F3 0.7878(4) 1.1542(3) 0.23004(13) 0.0903(9) Uani d . 1 1
F F1 0.7058(4) 0.7458(3) 0.24699(12) 0.0897(8) Uani d . 1 1
C C5 0.5124(5) 0.9963(4) 0.04139(17) 0.0451(8) Uani d . 1 1
C C6 0.3393(5) 1.0854(4) 0.02680(18) 0.0491(9) Uani d . 1 1
C C3 0.8125(6) 1.0019(5) 0.2037(2) 0.0608(10) Uani d . 1 1
C C2 0.6375(6) 0.8962(5) 0.22754(19) 0.0595(11) Uani d . 1 1
C C10 0.6062(6) 0.9131(5) -0.01323(19) 0.0575(10) Uani d . 1 1
H H10 0.7199 0.8541 -0.0031 0.069 Uiso calc R 1 1
C C7 0.2663(6) 1.0832(5) -0.0431(2) 0.0605(11) Uani d . 1 1
H H7 0.1501 1.1383 -0.0536 0.073 Uiso calc R 1 1
C C8 0.3635(7) 1.0009(5) -0.0966(2) 0.0688(12) Uani d . 1 1
H H8 0.3133 1.0027 -0.1430 0.083 Uiso calc R 1 1
C C9 0.5346(7) 0.9155(5) -0.0827(2) 0.0716(13) Uani d . 1 1
H H9 0.6004 0.8608 -0.1192 0.086 Uiso calc R 1 1
C C4 0.7993(5) 0.9997(5) 0.12353(18) 0.0583(10) Uani d . 1 1
H H4A 0.8623 1.0946 0.1025 0.070 Uiso calc R 1 1
H H4B 0.8569 0.9013 0.1036 0.070 Uiso calc R 1 1
C C1 0.5016(6) 0.8845(5) 0.16406(19) 0.0665(12) Uani d . 1 1
H H1A 0.5021 0.7752 0.1440 0.080 Uiso calc R 1 1
H H1B 0.3679 0.9136 0.1771 0.080 Uiso calc R 1 1
N N1 0.5854(4) 1.0035(4) 0.11341(14) 0.0466(7) Uani d . 1 1
N N2 0.2447(6) 1.1710(5) 0.0805(2) 0.0653(10) Uani d . 1 1
H H2A 0.312(7) 1.201(6) 0.116(3) 0.091(19) Uiso d . 1 1
H H2B 0.171(9) 1.254(9) 0.068(3) 0.17(3) Uiso d . 1 1
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
C10 C5 C6 119.8(3)
C10 C5 N1 123.5(3)
C6 C5 N1 116.6(3)
N2 C6 C7 121.3(4)
N2 C6 C5 120.7(3)
C7 C6 C5 118.1(3)
F4 C3 F3 106.8(3)
F4 C3 C4 113.7(3)
F3 C3 C4 111.6(3)
F4 C3 C2 112.5(3)
F3 C3 C2 108.6(3)
C4 C3 C2 103.7(3)
F2 C2 F1 103.9(3)
F2 C2 C1 113.9(4)
F1 C2 C1 111.1(3)
F2 C2 C3 112.7(4)
F1 C2 C3 108.8(3)
C1 C2 C3 106.4(3)
C5 C10 C9 121.5(4)
C5 C10 H10 119.3
C9 C10 H10 119.3
C8 C7 C6 121.0(4)
C8 C7 H7 119.5
C6 C7 H7 119.5
C7 C8 C9 121.1(4)
C7 C8 H8 119.5
C9 C8 H8 119.5
C8 C9 C10 118.6(4)
C8 C9 H9 120.7
C10 C9 H9 120.7
N1 C4 C3 100.8(3)
N1 C4 H4A 111.6
C3 C4 H4A 111.6
N1 C4 H4B 111.6
C3 C4 H4B 111.6
H4A C4 H4B 109.4
N1 C1 C2 103.1(3)
N1 C1 H1A 111.2
C2 C1 H1A 111.2
N1 C1 H1B 111.2
C2 C1 H1B 111.2
H1A C1 H1B 109.1
C5 N1 C4 117.6(3)
C5 N1 C1 116.2(3)
C4 N1 C1 106.7(3)
C6 N2 H2A 117(3)
C6 N2 H2B 118(4)
H2A N2 H2B 107(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F2 C2 1.350(5)
F4 C3 1.347(5)
F3 C3 1.350(5)
F1 C2 1.365(5)
C5 C10 1.382(5)
C5 C6 1.409(5)
C5 N1 1.434(5)
C6 N2 1.381(5)
C6 C7 1.395(5)
C3 C4 1.498(6)
C3 C2 1.536(6)
C2 C1 1.505(6)
C10 C9 1.384(6)
C10 H10 0.9300
C7 C8 1.374(6)
C7 H7 0.9300
C8 C9 1.380(6)
C8 H8 0.9300
C9 H9 0.9300
C4 N1 1.465(5)
C4 H4A 0.9700
C4 H4B 0.9700
C1 N1 1.472(5)
C1 H1A 0.9700
C1 H1B 0.9700
N2 H2A 0.84(5)
N2 H2B 0.87(7)
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
N2 H2A F1 3_655 0.84(5) 2.59(5) 3.295(8) 142(4)
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
C10 C5 C6 N2 -179.2(4)
N1 C5 C6 N2 -1.6(5)
C10 C5 C6 C7 1.3(5)
N1 C5 C6 C7 178.9(3)
F4 C3 C2 F2 93.9(4)
F3 C3 C2 F2 -24.1(4)
C4 C3 C2 F2 -142.8(3)
F4 C3 C2 F1 -20.8(4)
F3 C3 C2 F1 -138.8(3)
C4 C3 C2 F1 102.5(3)
F4 C3 C2 C1 -140.6(4)
F3 C3 C2 C1 101.4(4)
C4 C3 C2 C1 -17.3(4)
C6 C5 C10 C9 0.3(5)
N1 C5 C10 C9 -177.1(4)
N2 C6 C7 C8 178.5(4)
C5 C6 C7 C8 -2.0(6)
C6 C7 C8 C9 1.1(6)
C7 C8 C9 C10 0.6(6)
C5 C10 C9 C8 -1.3(6)
F4 C3 C4 N1 159.5(3)
F3 C3 C4 N1 -79.6(4)
C2 C3 C4 N1 37.0(4)
F2 C2 C1 N1 115.4(4)
F1 C2 C1 N1 -127.7(4)
C3 C2 C1 N1 -9.4(4)
C10 C5 N1 C4 31.8(5)
C6 C5 N1 C4 -145.8(4)
C10 C5 N1 C1 -96.3(4)
C6 C5 N1 C1 86.2(4)
C3 C4 N1 C5 -177.7(3)
C3 C4 N1 C1 -45.2(4)
C2 C1 N1 C5 167.3(3)
C2 C1 N1 C4 34.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656948
