#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:54:10 +0200 (mar 06 de oct de 2020) $
#$Revision: 257700 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/87/1558783.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_1558783
loop_
_publ_author_name
'Reichel, Marco'
'Unger, Cornelia'
'Dubovnik, Sviatlana'
'Roidl, Andreas'
'Kornath, Andreas'
'Karaghiosoff, Konstantin'
_publ_section_title
;
 Synthesis, structural and toxicological investigations of quarternary
 phosphonium salts containing the P-bonded bioisosteric CH2F moiety
;
_journal_issue                   33
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14306
_journal_page_last               14315
_journal_paper_doi               10.1039/D0NJ02310H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C4 H11 F I P'
_chemical_formula_sum            'C4 H11 F I P'
_chemical_formula_weight         236.00
_chemical_name_systematic
;
(Fluoromethyl)trimethylphosphonium iodide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-04 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1430(5)
_cell_length_b                   7.3397(3)
_cell_length_c                   9.2655(5)
_cell_measurement_reflns_used    2382
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      31.8860
_cell_measurement_theta_min      4.8560
_cell_volume                     825.80(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8368
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.493
_diffrn_reflns_theta_min         4.356
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       neadle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     43
_refine_ls_number_reflns         1346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0223
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0189P)²+0.0931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0504
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1124
_reflns_number_total             1346
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02310h2.cif
_cod_data_source_block           test1
_cod_depositor_comments
;Adding full bibliography for 1558783--1558787.cif.

 Adding full bibliography for 1558783--1558787.cif.
;
_cod_database_code               1558783
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_res_file
;
TITL test1 in Pnma
    test1.res
    created by SHELXL-2018/3 at 08:43:17 on 23-Jul-2019
CELL  0.71073  12.1430   7.3397   9.2655   90.000   90.000   90.000
ZERR     4.00   0.0005   0.0003   0.0005    0.000    0.000    0.000
LATT   1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y, 1/2 - Z
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    F    P    I
UNIT  16   44   4    4    4
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
MERG   2
SHEL 1000 0.7
FMAP   2
PLAN   -25
ACTA
EXYZ C3 C3B
EADP C3 C3B
L.S.  20
TEMP  -130.00
WGHT    0.018900    0.093100
FVAR       0.49704
I1    5    0.597720    0.250000    0.125873    10.50000    0.02413    0.02877 =
         0.03672    0.00000    0.00118    0.00000
P1    4    0.284562    0.750000    0.327955    10.50000    0.01831    0.02667 =
         0.02211    0.00000    0.00040    0.00000
C1    1    0.183809    0.750000    0.190140    10.50000    0.02689    0.04607 =
         0.02956    0.00000   -0.00774    0.00000
AFIX  33
H1A   2    0.220139    0.750000    0.095695    10.50000   -1.50000
H1B   2    0.137727    0.640981    0.199177    10.50000   -1.50000
H1C   2    0.137727    0.859019    0.199178    10.50000   -1.50000
AFIX   0
C2    1    0.220028    0.750000    0.499411    10.50000    0.03688    0.04170 =
         0.02356    0.00000    0.00623    0.00000
AFIX  33
H2A   2    0.276366    0.750000    0.575144    10.50000   -1.50000
H2B   2    0.174008    0.859019    0.508972    10.50000   -1.50000
H2C   2    0.174008    0.640981    0.508972    10.50000   -1.50000
AFIX   0
PART 1 10.5
C3    1    0.370108    0.552340    0.310155    10.50000    0.02694    0.03261 =
         0.03816   -0.00219   -0.00079    0.00498
AFIX  23
H3A   2    0.324098    0.440991    0.310738    10.50000   -1.20000
H3B   2    0.410728    0.556982    0.217586    10.50000   -1.20000
AFIX   0
F1    3    0.442924    0.547963    0.423046    10.50000    0.03937    0.05591 =
         0.04355    0.00247   -0.01098    0.01612
PART 2 10.5
C3B   1    0.370108    0.552340    0.310155    10.50000    0.02694    0.03261 =
         0.03816   -0.00219   -0.00079    0.00498
AFIX  33
H3BA  2    0.425902    0.552494    0.386577    10.50000   -1.50000
H3BB  2    0.324725    0.442422    0.318406    10.50000   -1.50000
H3BC  2    0.406481    0.554004    0.215747    10.50000   -1.50000
PART 0
AFIX   0
HKLF    4




REM  test1 in Pnma
REM wR2 = 0.0504, GooF = S = 1.102, Restrained GooF = 1.102 for all data
REM R1 = 0.0223 for 1124 Fo > 4sig(Fo) and 0.0313 for all 1346 data
REM 43 parameters refined using 0 restraints

END

WGHT      0.0189      0.0931

REM Highest difference peak  1.020,  deepest hole -0.573,  1-sigma level  0.102
Q1    1   0.7027  0.2500  0.3692  10.50000  0.05    1.02
Q2    1   0.7266  0.2500  0.5720  10.50000  0.05    0.71
Q3    1   0.5954  0.2500  0.6355  10.50000  0.05    0.52
Q4    1   0.7143  0.2500  0.0833  10.50000  0.05    0.47
Q5    1   0.5962  0.2500  0.2075  10.50000  0.05    0.44
Q6    1   0.6742  0.1375  0.6708  11.00000  0.05    0.41
Q7    1   0.7737  0.2500  0.7548  10.50000  0.05    0.41
Q8    1   0.7061  0.2500  0.4745  10.50000  0.05    0.40
Q9    1   0.8730  0.2500  0.6798  10.50000  0.05    0.38
Q10   1   0.4798  0.2500  0.6720  10.50000  0.05    0.38
Q11   1   0.5931  0.0851  0.1895  11.00000  0.05    0.35
Q12   1   0.7928  0.2500  0.5975  10.50000  0.05    0.34
Q13   1   0.8585  0.2500  0.5005  10.50000  0.05    0.33
Q14   1   0.4209  0.2500  0.2287  10.50000  0.05    0.33
Q15   1   0.8382  0.1009  0.0985  11.00000  0.05    0.31
Q16   1   0.6130 -0.0268  0.5793  11.00000  0.05    0.30
Q17   1   0.4989  0.2500 -0.0306  10.50000  0.05    0.28
Q18   1   0.6487  0.2500  0.1182  10.50000  0.05    0.28
Q19   1   0.6794  0.2500  0.2039  10.50000  0.05    0.27
Q20   1   0.5785  0.2500  0.8218  10.50000  0.05    0.26
Q21   1   0.6092  0.1331  0.8601  11.00000  0.05    0.26
Q22   1   0.4910  0.1355  0.3652  11.00000  0.05    0.26
Q23   1   0.5565 -0.0275  0.1830  11.00000  0.05    0.26
Q24   1   0.5958  0.0867  0.0729  11.00000  0.05    0.26
Q25   1   0.6744  0.0761  0.1184  11.00000  0.05    0.25
;
_shelx_res_checksum              63382
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.59772(2) 0.250000 0.12587(2) 0.02987(8) Uani 1 2 d S T P . .
P1 P 0.28456(6) 0.750000 0.32796(9) 0.02236(16) Uani 1 2 d S T P . .
C1 C 0.1838(3) 0.750000 0.1901(4) 0.0342(8) Uani 1 2 d S T P A .
H1A H 0.220139 0.750000 0.095695 0.051 Uiso 1 2 calc R U P . .
H1B H 0.137727 0.640981 0.199177 0.051 Uiso 0.5 1 calc R U P . .
H1C H 0.137727 0.859019 0.199178 0.051 Uiso 0.5 1 calc R U P . .
C2 C 0.2200(3) 0.750000 0.4994(4) 0.0340(7) Uani 1 2 d S T P A .
H2A H 0.276366 0.750000 0.575144 0.051 Uiso 1 2 calc R U P . .
H2B H 0.174008 0.859019 0.508972 0.051 Uiso 0.5 1 calc R U P . .
H2C H 0.174008 0.640981 0.508972 0.051 Uiso 0.5 1 calc R U P . .
C3 C 0.37011(19) 0.5523(3) 0.3102(3) 0.0326(5) Uani 0.5 1 d . . P A 1
H3A H 0.324098 0.440991 0.310738 0.039 Uiso 0.5 1 calc R U P A 1
H3B H 0.410728 0.556982 0.217586 0.039 Uiso 0.5 1 calc R U P A 1
F1 F 0.4429(2) 0.5480(5) 0.4230(4) 0.0463(8) Uani 0.5 1 d . . P A 1
C3B C 0.37011(19) 0.5523(3) 0.3102(3) 0.0326(5) Uani 0.5 1 d . . P A 2
H3BA H 0.425902 0.552494 0.386577 0.049 Uiso 0.5 1 calc R U P A 2
H3BB H 0.324725 0.442422 0.318406 0.049 Uiso 0.5 1 calc R U P A 2
H3BC H 0.406481 0.554004 0.215747 0.049 Uiso 0.5 1 calc R U P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02413(11) 0.02877(13) 0.03672(14) 0.000 0.00118(8) 0.000
P1 0.0183(3) 0.0267(4) 0.0221(4) 0.000 0.0004(3) 0.000
C1 0.0269(15) 0.046(2) 0.0296(19) 0.000 -0.0077(13) 0.000
C2 0.0369(18) 0.0417(19) 0.0236(17) 0.000 0.0062(14) 0.000
C3 0.0269(11) 0.0326(13) 0.0382(14) -0.0022(11) -0.0008(10) 0.0050(10)
F1 0.0394(16) 0.056(2) 0.0436(19) 0.0025(16) -0.0110(14) 0.0161(16)
C3B 0.0269(11) 0.0326(13) 0.0382(14) -0.0022(11) -0.0008(10) 0.0050(10)
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C1 P1 C2 109.97(17) . . ?
C1 P1 C3B 109.55(11) . . ?
C2 P1 C3B 109.82(11) . . ?
C1 P1 C3 109.55(11) . . ?
C2 P1 C3 109.82(11) . . ?
C1 P1 C3 109.55(11) . 8_575 ?
C2 P1 C3 109.82(11) . 8_575 ?
C3B P1 C3 108.12(16) . 8_575 ?
C3 P1 C3 108.12(16) . 8_575 ?
F1 C3 P1 108.8(2) . . ?
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 C1 1.768(3) . ?
P1 C2 1.771(3) . ?
P1 C3B 1.792(2) . ?
P1 C3 1.792(2) . ?
P1 C3 1.792(2) 8_575 ?
C3 F1 1.370(4) . ?
