#------------------------------------------------------------------------------
#$Date: 2019-11-23 07:02:17 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/75/4347557.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_4347557
loop_
_publ_author_name
'Schläfer, J'
'Graf, D.'
'Fornalczyk, G.'
'Mettenbörger, A'
'Mathur, S.'
_publ_section_title
;
 Fluorinated Cerium(IV) Enaminolates: Alternative Precursors for Chemical
 Vapor Deposition of CeO2 Thin Films.
;
_journal_issue                   11
_journal_name_full               'Inorganic chemistry'
_journal_page_first              5422
_journal_page_last               5429
_journal_paper_doi               10.1021/acs.inorgchem.6b00348
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C10 H10 F6 N2 O2'
_chemical_formula_weight         304.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                109.754(15)
_cell_angle_beta                 101.386(16)
_cell_angle_gamma                97.169(14)
_cell_formula_units_Z            1
_cell_length_a                   5.7104(7)
_cell_length_b                   7.3062(8)
_cell_length_c                   8.2087(12)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.915
_cell_measurement_theta_min      2.728
_cell_volume                     309.10(8)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 'not measured'
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'IPDS 2T (Stoe & Cie)'
_diffrn_measurement_method       'ω and φ 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  0.0370
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3749
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.915
_diffrn_reflns_theta_min         2.728
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9177
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
The absorption correction (X-RED; Stoe & Cie, 2001)
was preformed after optimizing the crystal shape
using X-SHAPE (Stoe & Cie, 1999).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             154
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0686P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                941
_reflns_number_total             1370
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b00348_si_002.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4347557
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1A F 0.2419(16) 0.9025(8) 0.4366(10) 0.0851(16) Uani 0.69(2) 1 d . . P
F2A F -0.0984(15) 0.7032(9) 0.3618(14) 0.103(2) Uani 0.69(2) 1 d . . P
F3A F 0.0082(10) 0.8368(8) 0.1885(6) 0.0705(13) Uani 0.69(2) 1 d . . P
F1B F 0.201(4) 0.870(4) 0.475(3) 0.121(6) Uani 0.31(2) 1 d . . P
F2B F -0.1307(18) 0.6841(17) 0.317(2) 0.087(4) Uani 0.31(2) 1 d . . P
F3B F 0.050(4) 0.859(2) 0.208(2) 0.112(5) Uani 0.31(2) 1 d . . P
O1 O 0.3162(3) 0.59685(17) 0.10902(18) 0.0593(4) Uani 1 1 d . . .
N1 N 0.4671(3) 0.25420(19) 0.13546(19) 0.0454(4) Uani 1 1 d . . .
C1 C 0.5795(3) 0.0812(2) 0.0852(2) 0.0473(4) Uani 1 1 d . . .
H2 H 0.6032 0.0310 0.1813 0.057 Uiso 1 1 calc R U .
H3 H 0.7383 0.1202 0.0673 0.057 Uiso 1 1 calc R U .
C2 C 0.3439(3) 0.2905(2) 0.2562(2) 0.0499(5) Uani 1 1 d . . .
H4 H 0.3379 0.2040 0.3171 0.060 Uiso 1 1 calc R U .
C5 C 0.2210(4) 0.4440(2) 0.3038(2) 0.0534(5) Uani 1 1 d . . .
H8 H 0.1359 0.4519 0.3907 0.064 Uiso 1 1 calc R U .
C6 C 0.2193(3) 0.5871(2) 0.2270(2) 0.0414(4) Uani 1 1 d . . .
C7 C 0.0850(4) 0.7545(2) 0.3034(2) 0.0507(4) Uani 1 1 d . . .
H1 H 0.484(4) 0.334(3) 0.082(3) 0.062(6) 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'
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'
O O 0.0106 0.0060 '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
F1B F1A C7 82(2) . .
F1A F1B C7 75(2) . .
C2 N1 C1 123.55(14) . .
C2 N1 H1 119.0(12) . .
C1 N1 H1 117.5(12) . .
N1 C1 C1 110.84(16) . 2_655
N1 C1 H2 109.5 . .
C1 C1 H2 109.5 2_655 .
N1 C1 H3 109.5 . .
C1 C1 H3 109.5 2_655 .
H2 C1 H3 108.1 . .
N1 C2 C5 126.91(14) . .
N1 C2 H4 116.5 . .
C5 C2 H4 116.5 . .
C2 C5 C6 122.76(15) . .
C2 C5 H8 118.6 . .
C6 C5 H8 118.6 . .
O1 C6 C5 127.31(14) . .
O1 C6 C7 116.81(13) . .
C5 C6 C7 115.86(13) . .
F3B C7 F2A 116.2(8) . .
F3B C7 F2B 106.6(9) . .
F2A C7 F2B 15.4(8) . .
F3B C7 F3A 11.3(10) . .
F2A C7 F3A 108.1(4) . .
F2B C7 F3A 97.0(7) . .
F3B C7 F1A 92.8(9) . .
F2A C7 F1A 108.1(5) . .
F2B C7 F1A 122.1(7) . .
F3A C7 F1A 103.3(4) . .
F3B C7 F1B 111.1(11) . .
F2A C7 F1B 87.4(12) . .
F2B C7 F1B 102.4(13) . .
F3A C7 F1B 120.1(12) . .
F1A C7 F1B 22.7(15) . .
F3B C7 C6 112.9(6) . .
F2A C7 C6 115.2(2) . .
F2B C7 C6 111.9(5) . .
F3A C7 C6 112.5(2) . .
F1A C7 C6 109.0(4) . .
F1B C7 C6 111.3(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1A F1B 0.53(4) .
F1A C7 1.319(7) .
F2A C7 1.299(5) .
F3A C7 1.315(4) .
F1B C7 1.348(16) .
F2B C7 1.313(12) .
F3B C7 1.276(11) .
O1 C6 1.2236(19) .
N1 C2 1.301(2) .
N1 C1 1.4606(17) .
N1 H1 0.85(2) .
C1 C1 1.515(3) 2_655
C1 H2 0.9700 .
C1 H3 0.9700 .
C2 C5 1.383(2) .
C2 H4 0.9300 .
C5 C6 1.391(2) .
C5 H8 0.9300 .
C6 C7 1.544(2) .
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
_geom_torsion_site_symmetry_4
C2 N1 C1 C1 99.1(2) 2_655
C1 N1 C2 C5 -176.02(18) .
N1 C2 C5 C6 -1.6(3) .
C2 C5 C6 O1 1.7(3) .
C2 C5 C6 C7 -176.67(17) .
F1B F1A C7 F3B 145(3) .
F1B F1A C7 F2A 26(3) .
F1B F1A C7 F2B 33(3) .
F1B F1A C7 F3A 140(3) .
F1B F1A C7 C6 -100(3) .
F1A F1B C7 F3B -38(3) .
F1A F1B C7 F2A -155(3) .
F1A F1B C7 F2B -152(2) .
F1A F1B C7 F3A -46(3) .
F1A F1B C7 C6 88(3) .
O1 C6 C7 F3B 13.6(11) .
C5 C6 C7 F3B -167.8(11) .
O1 C6 C7 F2A 150.4(6) .
C5 C6 C7 F2A -31.1(6) .
O1 C6 C7 F2B 133.9(8) .
C5 C6 C7 F2B -47.5(8) .
O1 C6 C7 F3A 25.9(4) .
C5 C6 C7 F3A -155.5(3) .
O1 C6 C7 F1A -88.0(4) .
C5 C6 C7 F1A 90.5(4) .
O1 C6 C7 F1B -112.1(18) .
C5 C6 C7 F1B 66.4(18) .
