#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/21/7002175.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_7002175
loop_
_publ_author_name
'Pailloux, Sylvie'
'Shirima, Cornel Edicome'
'Ray, Alisha D.'
'Duesler, Eileen N.'
'Smith, Karen Ann'
'Paine, Robert T.'
'Klaehn, John R.'
'McIlwain, Michael E.'
'Hay, Benjamin P.'
_publ_section_title
;
 Synthesis and lanthanide coordination chemistry of trifluoromethyl
 derivatives of phosphinoylmethyl pyridine N-oxides
;
_journal_issue                   36
_journal_name_full               'Dalton Transactions'
_journal_page_first              7486
_journal_page_last               7493
_journal_paper_doi               10.1039/b905947d
_journal_year                    2009
_chemical_formula_moiety         'C20 H14 F6 N O2 P'
_chemical_formula_sum            'C20 H14 F6 N O2 P'
_chemical_formula_weight         445.29
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.198(4)
_cell_angle_beta                 81.657(4)
_cell_angle_gamma                72.516(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8219(6)
_cell_length_b                   8.8196(7)
_cell_length_c                   14.4992(12)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      65.73
_cell_measurement_theta_min      5.47
_cell_volume                     942.18(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      225(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25744
_diffrn_reflns_theta_full        33.07
_diffrn_reflns_theta_max         33.07
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker,SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         7013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0426
_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[σ²(Fo²)+(0.0573P)²+0.4033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                5849
_reflns_number_total             7013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905947d.txt
_cod_data_source_block           rpsl32
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7002175
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.17704(4) 0.65694(3) 0.20684(2) 0.02238(8) Uani 1 1 d . . .
O1 O 0.67512(13) 0.62155(13) 0.05306(7) 0.0340(2) Uani 1 1 d . . .
O2 O 0.01323(13) 0.78981(11) 0.19093(7) 0.0317(2) Uani 1 1 d . . .
N1 N 0.54928(15) 0.72501(13) 0.01041(7) 0.0261(2) Uani 1 1 d . . .
C1 C 0.5987(2) 0.82273(17) -0.06018(9) 0.0336(3) Uani 1 1 d . . .
H1A H 0.7217 0.8145 -0.0770 0.040 Uiso 1 1 calc R . .
C2 C 0.4718(2) 0.93317(17) -0.10718(10) 0.0396(3) Uani 1 1 d . . .
H2 H 0.5084 0.9992 -0.1562 0.048 Uiso 1 1 calc R . .
C3 C 0.2905(2) 0.94790(18) -0.08279(10) 0.0397(3) Uani 1 1 d . . .
H3 H 0.2022 1.0255 -0.1133 0.048 Uiso 1 1 calc R . .
C4 C 0.2423(2) 0.84525(17) -0.01228(10) 0.0330(3) Uani 1 1 d . . .
H4 H 0.1196 0.8526 0.0047 0.040 Uiso 1 1 calc R . .
C5 C 0.37147(17) 0.73162(14) 0.03401(8) 0.0247(2) Uani 1 1 d . . .
C6 C 0.32903(17) 0.60373(14) 0.10013(8) 0.0256(2) Uani 1 1 d . . .
H6A H 0.4436 0.5330 0.1182 0.031 Uiso 1 1 calc R . .
H6B H 0.2782 0.5411 0.0656 0.031 Uiso 1 1 calc R . .
C7 C 0.30011(16) 0.70629(14) 0.29097(8) 0.0232(2) Uani 1 1 d . . .
C8 C 0.47638(17) 0.71115(15) 0.26066(9) 0.0266(2) Uani 1 1 d . . .
H8 H 0.5292 0.6798 0.2005 0.032 Uiso 1 1 calc R . .
C9 C 0.57571(19) 0.76114(17) 0.31719(10) 0.0319(3) Uani 1 1 d . . .
H9 H 0.6935 0.7648 0.2949 0.038 Uiso 1 1 calc R . .
C10 C 0.5011(2) 0.80523(18) 0.40602(10) 0.0347(3) Uani 1 1 d . . .
H10 H 0.5683 0.8376 0.4448 0.042 Uiso 1 1 calc R . .
C11 C 0.3267(2) 0.80166(18) 0.43788(9) 0.0343(3) Uani 1 1 d . . .
H11 H 0.2762 0.8318 0.4985 0.041 Uiso 1 1 calc R . .
C12 C 0.22502(18) 0.75412(15) 0.38150(9) 0.0279(2) Uani 1 1 d . . .
C13 C 0.0350(2) 0.7613(2) 0.42135(11) 0.0413(3) Uani 1 1 d . . .
C14 C 0.12107(16) 0.46866(15) 0.23385(8) 0.0250(2) Uani 1 1 d . . .
C15 C -0.02885(18) 0.47035(17) 0.19130(10) 0.0320(3) Uani 1 1 d . . .
H15 H -0.0921 0.5648 0.1602 0.038 Uiso 1 1 calc R . .
C16 C -0.0864(2) 0.3353(2) 0.19407(12) 0.0400(3) Uani 1 1 d . . .
H16 H -0.1863 0.3388 0.1640 0.048 Uiso 1 1 calc R . .
C17 C 0.0020(2) 0.1968(2) 0.24049(12) 0.0426(3) Uani 1 1 d . . .
H17 H -0.0376 0.1057 0.2429 0.051 Uiso 1 1 calc R . .
C18 C 0.1505(2) 0.19234(17) 0.28391(10) 0.0355(3) Uani 1 1 d . . .
H18 H 0.2106 0.0979 0.3162 0.043 Uiso 1 1 calc R . .
C19 C 0.21150(18) 0.32602(15) 0.28024(9) 0.0273(2) Uani 1 1 d . . .
C20 C 0.3754(2) 0.31067(16) 0.32674(11) 0.0349(3) Uani 1 1 d . . .
F1 F -0.02517(13) 0.65162(13) 0.39137(7) 0.0436(2) Uani 1 1 d . . .
F2 F 0.0161(2) 0.7440(3) 0.51332(8) 0.0916(6) Uani 1 1 d . . .
F3 F -0.08304(17) 0.90171(16) 0.39882(13) 0.0766(4) Uani 1 1 d . . .
F4 F 0.33824(16) 0.39338(13) 0.40298(7) 0.0501(3) Uani 1 1 d . . .
F5 F 0.49987(13) 0.36282(12) 0.26951(8) 0.0462(2) Uani 1 1 d . . .
F6 F 0.45834(17) 0.16036(12) 0.35370(9) 0.0588(3) 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'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
O2 P1 C7 110.83(6) . . ?
O2 P1 C6 112.74(6) . . ?
C7 P1 C6 108.69(6) . . ?
O2 P1 C14 110.77(6) . . ?
C7 P1 C14 115.13(5) . . ?
C6 P1 C14 98.13(6) . . ?
O1 N1 C1 118.71(12) . . ?
O1 N1 C5 120.83(11) . . ?
C1 N1 C5 120.43(11) . . ?
N1 C1 C2 120.94(14) . . ?
N1 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C1 C2 C3 120.29(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 118.13(13) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 121.38(14) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
N1 C5 C4 118.73(12) . . ?
N1 C5 C6 117.68(10) . . ?
C4 C5 C6 123.17(12) . . ?
C5 C6 P1 119.53(8) . . ?
C5 C6 H6A 107.4 . . ?
P1 C6 H6A 107.4 . . ?
C5 C6 H6B 107.4 . . ?
P1 C6 H6B 107.4 . . ?
H6A C6 H6B 107.0 . . ?
C8 C7 C12 117.69(11) . . ?
C8 C7 P1 117.46(9) . . ?
C12 C7 P1 124.58(10) . . ?
C9 C8 C7 121.70(12) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 119.81(13) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.74(13) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.99(12) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 120.06(12) . . ?
C11 C12 C13 116.64(12) . . ?
C7 C12 C13 123.28(12) . . ?
F2 C13 F1 106.70(15) . . ?
F2 C13 F3 106.38(16) . . ?
F1 C13 F3 105.25(14) . . ?
F2 C13 C12 112.15(14) . . ?
F1 C13 C12 113.83(12) . . ?
F3 C13 C12 111.97(14) . . ?
C15 C14 C19 117.82(12) . . ?
C15 C14 P1 110.74(9) . . ?
C19 C14 P1 131.11(10) . . ?
C16 C15 C14 121.37(14) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C15 120.30(14) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.46(14) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 120.81(14) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C14 120.23(13) . . ?
C18 C19 C20 117.68(12) . . ?
C14 C19 C20 122.10(11) . . ?
F4 C20 F6 106.21(12) . . ?
F4 C20 F5 106.52(13) . . ?
F6 C20 F5 105.97(13) . . ?
F4 C20 C19 112.93(13) . . ?
F6 C20 C19 112.89(12) . . ?
F5 C20 C19 111.80(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.4822(9) . ?
P1 C7 1.8177(12) . ?
P1 C6 1.8180(13) . ?
P1 C14 1.8325(13) . ?
O1 N1 1.3064(14) . ?
N1 C1 1.3591(17) . ?
N1 C5 1.3682(17) . ?
C1 C2 1.371(2) . ?
C1 H1A 0.9400 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.3883(17) . ?
C4 H4 0.9400 . ?
C5 C6 1.4885(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.3970(17) . ?
C7 C12 1.4089(17) . ?
C8 C9 1.3905(18) . ?
C8 H8 0.9400 . ?
C9 C10 1.377(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.384(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.3911(19) . ?
C11 H11 0.9400 . ?
C12 C13 1.499(2) . ?
C13 F2 1.319(2) . ?
C13 F1 1.3284(19) . ?
C13 F3 1.346(2) . ?
C14 C15 1.3976(18) . ?
C14 C19 1.4028(17) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9400 . ?
C18 C19 1.3923(19) . ?
C18 H18 0.9400 . ?
C19 C20 1.498(2) . ?
C20 F4 1.3345(18) . ?
C20 F6 1.3354(16) . ?
C20 F5 1.3438(19) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 179.93(12) . . . . ?
C5 N1 C1 C2 2.11(19) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
C1 C2 C3 C4 -2.0(2) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
O1 N1 C5 C4 179.00(11) . . . . ?
C1 N1 C5 C4 -3.21(18) . . . . ?
O1 N1 C5 C6 -8.14(16) . . . . ?
C1 N1 C5 C6 169.65(11) . . . . ?
C3 C4 C5 N1 1.7(2) . . . . ?
C3 C4 C5 C6 -170.72(13) . . . . ?
N1 C5 C6 P1 124.22(10) . . . . ?
C4 C5 C6 P1 -63.27(15) . . . . ?
O2 P1 C6 C5 45.19(12) . . . . ?
C7 P1 C6 C5 -78.10(11) . . . . ?
C14 P1 C6 C5 161.82(10) . . . . ?
O2 P1 C7 C8 -118.67(10) . . . . ?
C6 P1 C7 C8 5.75(11) . . . . ?
C14 P1 C7 C8 114.64(10) . . . . ?
O2 P1 C7 C12 55.17(12) . . . . ?
C6 P1 C7 C12 179.60(10) . . . . ?
C14 P1 C7 C12 -71.52(12) . . . . ?
C12 C7 C8 C9 0.03(18) . . . . ?
P1 C7 C8 C9 174.31(10) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C7 1.0(2) . . . . ?
C10 C11 C12 C13 -177.45(14) . . . . ?
C8 C7 C12 C11 -0.97(18) . . . . ?
P1 C7 C12 C11 -174.80(10) . . . . ?
C8 C7 C12 C13 177.35(13) . . . . ?
P1 C7 C12 C13 3.52(19) . . . . ?
C11 C12 C13 F2 -27.7(2) . . . . ?
C7 C12 C13 F2 153.88(16) . . . . ?
C11 C12 C13 F1 -149.02(14) . . . . ?
C7 C12 C13 F1 32.6(2) . . . . ?
C11 C12 C13 F3 91.75(17) . . . . ?
C7 C12 C13 F3 -86.62(17) . . . . ?
O2 P1 C14 C15 29.00(11) . . . . ?
C7 P1 C14 C15 155.72(9) . . . . ?
C6 P1 C14 C15 -89.15(10) . . . . ?
O2 P1 C14 C19 -157.91(12) . . . . ?
C7 P1 C14 C19 -31.19(14) . . . . ?
C6 P1 C14 C19 83.94(13) . . . . ?
C19 C14 C15 C16 -0.4(2) . . . . ?
P1 C14 C15 C16 173.68(12) . . . . ?
C14 C15 C16 C17 1.1(2) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C18 C19 C14 1.2(2) . . . . ?
C17 C18 C19 C20 -178.48(14) . . . . ?
C15 C14 C19 C18 -0.72(19) . . . . ?
P1 C14 C19 C18 -173.41(11) . . . . ?
C15 C14 C19 C20 178.97(13) . . . . ?
P1 C14 C19 C20 6.3(2) . . . . ?
C18 C19 C20 F4 -110.65(14) . . . . ?
C14 C19 C20 F4 69.64(17) . . . . ?
C18 C19 C20 F6 9.85(19) . . . . ?
C14 C19 C20 F6 -169.86(13) . . . . ?
C18 C19 C20 F5 129.23(13) . . . . ?
C14 C19 C20 F5 -50.48(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25945913
