#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:43:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180312 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152656.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_7152656
loop_
_publ_author_name
'Kondratov, Ivan S.'
'Dolovanyuk, Violetta G.'
'Tolmachova, Nataliya A.'
'Gerus, Igor I.'
'Bergander, Klaus'
'Fröhlich, Roland'
'Haufe, Günter'
_publ_section_title
;
 Reactions of β-alkoxyvinyl polyfluoroalkyl ketones with ethyl
 isocyanoacetate and its use for the synthesis of new polyfluoroalkyl
 pyrroles and pyrrolidines.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8778
_journal_page_last               8785
_journal_paper_doi               10.1039/c2ob26176f
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C10 H10 F5 N O4'
_chemical_formula_weight         303.19
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   'at N from difmap, others geom'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.787(2)
_cell_angle_beta                 86.704(2)
_cell_angle_gamma                75.894(2)
_cell_formula_units_Z            2
_cell_length_a                   6.4262(3)
_cell_length_b                   9.9510(3)
_cell_length_c                   10.4639(4)
_cell_measurement_reflns_used    1431
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      4.08
_cell_volume                     623.11(4)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5389
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         4.30
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0646
_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)+(0.0490P)²+0.8369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1566
_reflns_number_gt                2073
_reflns_number_total             2442
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26176f.txt
_cod_data_source_block           haf5353
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7152656
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
O1 O 0.3500(3) 0.4651(2) 0.38239(19) 0.0417(5) Uani 1 1 d .
C1 C 0.3105(4) 0.3475(3) 0.4166(3) 0.0334(6) Uani 1 1 d .
C2 C 0.4153(4) 0.2329(3) 0.5329(2) 0.0306(5) Uani 1 1 d .
C3 C 0.3486(4) 0.1115(3) 0.5854(3) 0.0319(5) Uani 1 1 d .
H3 H 0.2441 0.0941 0.5368 0.038 Uiso 1 1 calc R
C4 C 0.4212(4) 0.0060(3) 0.7078(3) 0.0342(6) Uani 1 1 d .
H4 H 0.5357 0.0167 0.7530 0.041 Uiso 1 1 calc R
C5 C 0.3371(4) -0.1069(3) 0.7622(3) 0.0342(6) Uani 1 1 d .
O5 O 0.1753(4) -0.1443(2) 0.7166(2) 0.0494(6) Uani 1 1 d .
H5 H 0.0957 -0.0716 0.6678 0.074 Uiso 1 1 calc R
C6 C 0.4211(4) -0.2146(3) 0.8912(3) 0.0379(6) Uani 1 1 d .
F1 F 0.4432(3) -0.35041(17) 0.88240(19) 0.0540(5) Uani 1 1 d .
F2 F 0.6158(3) -0.2038(2) 0.92227(19) 0.0568(5) Uani 1 1 d .
C7 C 0.2795(6) -0.2023(4) 1.0119(3) 0.0503(8) Uani 1 1 d .
F3 F 0.2575(4) -0.0739(3) 1.0312(2) 0.0811(7) Uani 1 1 d .
F4 F 0.0878(3) -0.2199(3) 0.9964(2) 0.0798(7) Uani 1 1 d .
F5 F 0.3667(4) -0.3004(3) 1.12076(19) 0.0749(7) Uani 1 1 d .
O11 O 0.1690(3) 0.3089(2) 0.3561(2) 0.0437(5) Uani 1 1 d .
C12 C 0.0585(5) 0.4166(3) 0.2393(3) 0.0448(7) Uani 1 1 d .
H12A H 0.0122 0.3684 0.1801 0.054 Uiso 1 1 calc R
H12B H 0.1568 0.4736 0.1902 0.054 Uiso 1 1 calc R
C13 C -0.1309(6) 0.5128(4) 0.2819(4) 0.0654(10) Uani 1 1 d .
H13A H -0.2276 0.4560 0.3307 0.098 Uiso 1 1 calc R
H13B H -0.2047 0.5831 0.2041 0.098 Uiso 1 1 calc R
H13C H -0.0841 0.5623 0.3386 0.098 Uiso 1 1 calc R
N21 N 0.5839(4) 0.2685(2) 0.5874(2) 0.0337(5) Uani 1 1 d .
H21 H 0.573(5) 0.349(4) 0.592(3) 0.037(8) Uiso 1 1 d .
C22 C 0.7834(4) 0.1873(3) 0.6119(3) 0.0358(6) Uani 1 1 d .
H22 H 0.8843 0.2274 0.6405 0.043 Uiso 1 1 calc R
O23 O 0.8458(3) 0.0653(2) 0.6002(2) 0.0410(5) Uani 1 1 d .
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'
O O 0.0106 0.0060 '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
O1 C1 O11 124.1(2)
O1 C1 C2 122.6(2)
O11 C1 C2 113.3(2)
C3 C2 N21 123.8(2)
C3 C2 C1 123.2(2)
N21 C2 C1 113.0(2)
C2 C3 C4 126.3(2)
C2 C3 H3 116.9
C4 C3 H3 116.9
C5 C4 C3 124.3(2)
C5 C4 H4 117.9
C3 C4 H4 117.9
C4 C5 O5 128.5(2)
C4 C5 C6 121.8(2)
O5 C5 C6 109.7(2)
C5 O5 H5 109.5
F2 C6 F1 107.0(2)
F2 C6 C5 111.4(2)
F1 C6 C5 110.5(2)
F2 C6 C7 106.3(2)
F1 C6 C7 106.1(2)
C5 C6 C7 115.1(2)
F4 C7 F3 108.2(3)
F4 C7 F5 107.8(3)
F3 C7 F5 108.0(3)
F4 C7 C6 111.9(3)
F3 C7 C6 110.0(3)
F5 C7 C6 110.8(3)
C1 O11 C12 116.6(2)
O11 C12 C13 109.8(3)
O11 C12 H12A 109.7
C13 C12 H12A 109.7
O11 C12 H12B 109.7
C13 C12 H12B 109.7
H12A C12 H12B 108.2
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C22 N21 C2 125.7(2)
C22 N21 H21 113(2)
C2 N21 H21 120(2)
O23 C22 N21 125.4(2)
O23 C22 H22 117.3
N21 C22 H22 117.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.210(3)
C1 O11 1.322(3)
C1 C2 1.476(4)
C2 C3 1.342(3)
C2 N21 1.413(3)
C3 C4 1.428(4)
C3 H3 0.9400
C4 C5 1.335(4)
C4 H4 0.9400
C5 O5 1.339(3)
C5 C6 1.502(4)
O5 H5 0.8300
C6 F2 1.347(3)
C6 F1 1.353(3)
C6 C7 1.529(4)
C7 F4 1.312(4)
C7 F3 1.322(4)
C7 F5 1.323(4)
O11 C12 1.464(3)
C12 C13 1.485(5)
C12 H12A 0.9800
C12 H12B 0.9800
C13 H13A 0.9700
C13 H13B 0.9700
C13 H13C 0.9700
N21 C22 1.334(3)
N21 H21 0.80(3)
C22 O23 1.221(3)
C22 H22 0.9400
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
O1 C1 C2 C3 168.5(3)
O11 C1 C2 C3 -10.6(4)
O1 C1 C2 N21 -8.0(4)
O11 C1 C2 N21 172.9(2)
N21 C2 C3 C4 5.6(4)
C1 C2 C3 C4 -170.5(2)
C2 C3 C4 C5 173.8(3)
C3 C4 C5 O5 0.1(5)
C3 C4 C5 C6 179.8(2)
C4 C5 C6 F2 -16.1(4)
O5 C5 C6 F2 163.6(2)
C4 C5 C6 F1 -135.0(3)
O5 C5 C6 F1 44.8(3)
C4 C5 C6 C7 104.9(3)
O5 C5 C6 C7 -75.3(3)
F2 C6 C7 F4 -176.2(3)
F1 C6 C7 F4 -62.5(3)
C5 C6 C7 F4 60.0(4)
F2 C6 C7 F3 63.5(3)
F1 C6 C7 F3 177.2(2)
C5 C6 C7 F3 -60.3(3)
F2 C6 C7 F5 -55.8(3)
F1 C6 C7 F5 57.9(3)
C5 C6 C7 F5 -179.6(2)
O1 C1 O11 C12 1.1(4)
C2 C1 O11 C12 -179.8(2)
C1 O11 C12 C13 -85.3(3)
C3 C2 N21 C22 55.8(4)
C1 C2 N21 C22 -127.8(3)
C2 N21 C22 O23 -5.9(4)
