#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/39/7003961.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_7003961
loop_
_publ_author_name
'Caputo, Christine A.'
'Price, Jacquelyn T.'
'Jennings, Michael C.'
'McDonald, Robert'
'Jones, Nathan D.'
_publ_section_title
;
 N-Heterocyclic phosphenium cations: syntheses and cycloaddition
 reactions
;
_journal_issue                   26
_journal_name_full               'Dalton Transactions'
_journal_page_first              3461
_journal_page_last               3469
_journal_paper_doi               10.1039/b801684d
_journal_year                    2008
_chemical_formula_sum            'C15 H14 F3 N2 O3 P S'
_chemical_formula_weight         390.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 112.851(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6619(3)
_cell_length_b                   19.3867(5)
_cell_length_c                   8.7282(3)
_cell_measurement_reflns_used    16997
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.04
_cell_volume                     1662.52(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2001)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full .992
_diffrn_measured_fraction_theta_max .992
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7349
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.8483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_refine_diff_density_max         .428
_refine_diff_density_min         -.371
_refine_diff_density_rms         .055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0404
_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)+(0.0491P)²+0.9418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                3116
_reflns_number_total             3830
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b801684d.txt
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 21/c'
_cod_database_code               7003961
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.57662(5) 0.06771(2) 0.30708(6) 0.02677(13) Uani 1 1 d . . .
N1 N 0.64088(16) 0.14526(7) 0.32259(19) 0.0263(3) Uani 1 1 d . . .
C1 C 0.5700(2) 0.19297(9) 0.1837(2) 0.0304(4) Uani 1 1 d . . .
H3A H 0.6291 0.2046 0.1237 0.036 Uiso 1 1 calc R . .
H3B H 0.5455 0.2362 0.2260 0.036 Uiso 1 1 calc R . .
C2 C 0.4421(2) 0.15576(9) 0.0684(2) 0.0302(4) Uani 1 1 d . . .
H4A H 0.3599 0.1773 0.0741 0.036 Uiso 1 1 calc R . .
H4B H 0.4352 0.1579 -0.0479 0.036 Uiso 1 1 calc R . .
N2 N 0.45486(16) 0.08309(8) 0.12640(19) 0.0266(3) Uani 1 1 d . . .
C11 C 0.35704(11) 0.03208(5) 0.03836(14) 0.0265(4) Uani 1 1 d G . .
C12 C 0.35964(12) -0.03174(6) 0.11215(12) 0.0337(4) Uani 1 1 d G . .
H12A H 0.4245 -0.0405 0.2212 0.040 Uiso 1 1 calc R . .
C13 C 0.26735(14) -0.08267(5) 0.02632(16) 0.0379(5) Uani 1 1 d G . .
H13A H 0.2691 -0.1263 0.0768 0.045 Uiso 1 1 calc R . .
C14 C 0.17245(12) -0.06980(6) -0.13329(15) 0.0372(5) Uani 1 1 d G . .
H14A H 0.1094 -0.1046 -0.1919 0.045 Uiso 1 1 calc R . .
C15 C 0.16985(12) -0.00599(7) -0.20708(12) 0.0379(5) Uani 1 1 d G . .
H15A H 0.1050 0.0028 -0.3162 0.045 Uiso 1 1 calc R . .
C16 C 0.26214(13) 0.04495(5) -0.12126(14) 0.0317(4) Uani 1 1 d G . .
H16A H 0.2604 0.0886 -0.1717 0.038 Uiso 1 1 calc R . .
C21 C 0.76244(10) 0.16504(6) 0.45732(13) 0.0276(4) Uani 1 1 d G . .
C22 C 0.81258(12) 0.12399(5) 0.59884(15) 0.0324(4) Uani 1 1 d G . .
H22A H 0.7622 0.0850 0.6087 0.039 Uiso 1 1 calc R . .
C23 C 0.93647(13) 0.13992(6) 0.72587(13) 0.0369(5) Uani 1 1 d G . .
H23A H 0.9707 0.1119 0.8226 0.044 Uiso 1 1 calc R . .
C24 C 1.01022(10) 0.19691(7) 0.71137(14) 0.0386(5) Uani 1 1 d G . .
H24A H 1.0949 0.2078 0.7982 0.046 Uiso 1 1 calc R . .
C25 C 0.96008(12) 0.23796(6) 0.56986(16) 0.0384(5) Uani 1 1 d G . .
H25A H 1.0105 0.2769 0.5600 0.046 Uiso 1 1 calc R . .
C26 C 0.83619(13) 0.22203(6) 0.44283(13) 0.0330(4) Uani 1 1 d G . .
H26A H 0.8019 0.2501 0.3461 0.040 Uiso 1 1 calc R . .
O1 O 0.46420(13) 0.07978(6) 0.46807(16) 0.0293(3) Uani 1 1 d . . .
O2 O 0.39803(16) 0.19998(7) 0.40110(18) 0.0364(3) Uani 1 1 d . . .
O3 O 0.39960(16) 0.14815(8) 0.65715(17) 0.0388(3) Uani 1 1 d . . .
S34 S 0.38654(5) 0.13962(2) 0.48895(6) 0.02701(13) Uani 1 1 d . . .
C35 C 0.2110(2) 0.11107(10) 0.3783(3) 0.0331(4) Uani 1 1 d . . .
F3 F 0.18708(14) 0.05154(7) 0.43574(19) 0.0533(4) Uani 1 1 d . . .
F1 F 0.12496(13) 0.15718(7) 0.39367(18) 0.0502(4) Uani 1 1 d . . .
F2 F 0.18274(13) 0.10391(8) 0.21659(16) 0.0505(4) 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 '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
N2 P1 N1 93.58(8) . . ?
N2 P1 O1 99.93(7) . . ?
N1 P1 O1 99.50(7) . . ?
C21 N1 C1 121.37(13) . . ?
C21 N1 P1 122.26(11) . . ?
C1 N1 P1 116.28(12) . . ?
N1 C1 C2 106.66(14) . . ?
N1 C1 H3A 110.4 . . ?
C2 C1 H3A 110.4 . . ?
N1 C1 H3B 110.4 . . ?
C2 C1 H3B 110.4 . . ?
H3A C1 H3B 108.6 . . ?
N2 C2 C1 106.49(15) . . ?
N2 C2 H4A 110.4 . . ?
C1 C2 H4A 110.4 . . ?
N2 C2 H4B 110.4 . . ?
C1 C2 H4B 110.4 . . ?
H4A C2 H4B 108.6 . . ?
C11 N2 C2 121.55(14) . . ?
C11 N2 P1 122.28(11) . . ?
C2 N2 P1 115.79(12) . . ?
C12 C11 C16 120.0 . . ?
C12 C11 N2 119.26(9) . . ?
C16 C11 N2 120.72(9) . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C11 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
C22 C21 C26 120.0 . . ?
C22 C21 N1 119.50(9) . . ?
C26 C21 N1 120.32(10) . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C25 C24 H24A 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C21 C26 H26A 120.0 . . ?
S34 O1 P1 129.58(8) . . ?
O3 S34 O2 117.49(9) . . ?
O3 S34 O1 112.44(8) . . ?
O2 S34 O1 114.06(8) . . ?
O3 S34 C35 104.43(9) . . ?
O2 S34 C35 104.35(9) . . ?
O1 S34 C35 101.83(8) . . ?
F3 C35 F1 107.90(17) . . ?
F3 C35 F2 108.28(17) . . ?
F1 C35 F2 107.31(16) . . ?
F3 C35 S34 111.89(14) . . ?
F1 C35 S34 110.45(14) . . ?
F2 C35 S34 110.85(14) . . ?
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 N2 1.6344(16) . ?
P1 N1 1.6357(15) . ?
P1 O1 2.1850(14) . ?
N1 C21 1.4233(17) . ?
N1 C1 1.478(2) . ?
C1 C2 1.525(3) . ?
C1 H3A 0.9900 . ?
C1 H3B 0.9900 . ?
C2 N2 1.485(2) . ?
C2 H4A 0.9900 . ?
C2 H4B 0.9900 . ?
N2 C11 1.4262(17) . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12A 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13A 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14A 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C22 C23 1.3900 . ?
C22 H22A 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23A 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24A 0.9500 . ?
C25 C26 1.3900 . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
O1 S34 1.4772(13) . ?
O2 S34 1.4301(14) . ?
O3 S34 1.4294(14) . ?
S34 C35 1.827(2) . ?
C35 F3 1.322(2) . ?
C35 F1 1.325(2) . ?
C35 F2 1.331(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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 P1 N1 C21 -176.01(13) . . . . ?
O1 P1 N1 C21 83.30(13) . . . . ?
N2 P1 N1 C1 0.69(14) . . . . ?
O1 P1 N1 C1 -100.01(13) . . . . ?
C21 N1 C1 C2 -177.46(14) . . . . ?
P1 N1 C1 C2 5.8(2) . . . . ?
N1 C1 C2 N2 -10.1(2) . . . . ?
C1 C2 N2 C11 -175.22(14) . . . . ?
C1 C2 N2 P1 11.7(2) . . . . ?
N1 P1 N2 C11 179.40(13) . . . . ?
O1 P1 N2 C11 -80.30(13) . . . . ?
N1 P1 N2 C2 -7.58(15) . . . . ?
O1 P1 N2 C2 92.72(14) . . . . ?
C2 N2 C11 C12 -168.71(13) . . . . ?
P1 N2 C11 C12 3.92(17) . . . . ?
C2 N2 C11 C16 13.0(2) . . . . ?
P1 N2 C11 C16 -174.37(9) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
N2 C11 C12 C13 -178.30(13) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
N2 C11 C16 C15 178.28(13) . . . . ?
C1 N1 C21 C22 168.60(13) . . . . ?
P1 N1 C21 C22 -14.87(17) . . . . ?
C1 N1 C21 C26 -16.3(2) . . . . ?
P1 N1 C21 C26 160.25(9) . . . . ?
C26 C21 C22 C23 0.0 . . . . ?
N1 C21 C22 C23 175.13(13) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C21 0.0 . . . . ?
C22 C21 C26 C25 0.0 . . . . ?
N1 C21 C26 C25 -175.09(13) . . . . ?
N2 P1 O1 S34 -57.55(12) . . . . ?
N1 P1 O1 S34 37.82(12) . . . . ?
P1 O1 S34 O3 -143.24(10) . . . . ?
P1 O1 S34 O2 -6.23(14) . . . . ?
P1 O1 S34 C35 105.53(11) . . . . ?
O3 S34 C35 F3 -61.73(16) . . . . ?
O2 S34 C35 F3 174.36(14) . . . . ?
O1 S34 C35 F3 55.44(16) . . . . ?
O3 S34 C35 F1 58.48(16) . . . . ?
O2 S34 C35 F1 -65.43(16) . . . . ?
O1 S34 C35 F1 175.65(13) . . . . ?
O3 S34 C35 F2 177.29(13) . . . . ?
O2 S34 C35 F2 53.38(15) . . . . ?
O1 S34 C35 F2 -65.54(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652660
