#------------------------------------------------------------------------------
#$Date: 2025-08-21 13:25:49 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301846 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/89/7008990.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_7008990
loop_
_publ_author_name
'Corcoran, Christopher'
'Fawcett, John'
'Friedrichs, Steffi'
'Holloway, John H.'
'Hope, Eric G.'
'Russell, David R.'
'Saunders, Graham C.'
'Stuart, Alison M.'
_publ_section_title
;
 Structural and electronic impact of fluorine in the ortho positions of
 triphenylphosphine and 1,2-bis(diphenylphosphino)ethane; a comparison
 of 2,6-difluorophenyl- with pentafluorophenyl-phosphines
;
_journal_issue                   2
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              161
_journal_paper_doi               10.1039/a907759f
_journal_year                    2000
_chemical_formula_moiety         'C18 H9 F6 P'
_chemical_formula_sum            'C18 H9 F6 P'
_chemical_formula_weight         370.22
_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                 110.23(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.548(2)
_cell_length_b                   13.703(2)
_cell_length_c                   13.222(6)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      9.33
_cell_measurement_theta_min      5.26
_cell_volume                     1623.2(9)
_computing_cell_refinement       'XSCANS (Fait, 1991)'
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        'XSCANS (Fait, 1991)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Siemens P4 diffractometer'
_diffrn_measurement_method       'omega scan'
_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  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2590
_diffrn_reflns_theta_full        21.95
_diffrn_reflns_theta_max         21.95
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0441
_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)+(0.0347P)²+1.2352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                1430
_reflns_number_total             1941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            a907759f.txt
_cod_data_source_block           III
_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_cell_volume        1623.2(8)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7008990
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 0.82522(10) 0.28911(8) 0.24163(8) 0.0338(3) Uani 1 1 d . . .
F12 F 0.6987(3) 0.3785(2) -0.00040(19) 0.0755(9) Uani 1 1 d . . .
F16 F 0.5714(3) 0.18379(19) 0.2490(2) 0.0667(8) Uani 1 1 d . . .
F22 F 0.7735(3) 0.51219(18) 0.1865(2) 0.0654(8) Uani 1 1 d . . .
F26 F 1.1142(2) 0.2554(2) 0.2127(2) 0.0600(7) Uani 1 1 d . . .
F32 F 1.0267(2) 0.3086(2) 0.45958(18) 0.0696(8) Uani 1 1 d . . .
F36 F 0.5459(2) 0.4189(2) 0.25334(19) 0.0635(8) Uani 1 1 d . . .
C11 C 0.6431(4) 0.2849(3) 0.1318(3) 0.0352(10) Uani 1 1 d . . .
C12 C 0.5996(4) 0.3244(3) 0.0285(3) 0.0494(12) Uani 1 1 d . . .
C13 C 0.4602(5) 0.3108(4) -0.0488(4) 0.0698(16) Uani 1 1 d . . .
H13A H 0.4364 0.3388 -0.1167 0.084 Uiso 1 1 calc R . .
C14 C 0.3584(5) 0.2554(4) -0.0234(4) 0.0706(16) Uani 1 1 d . . .
H14A H 0.2633 0.2470 -0.0740 0.085 Uiso 1 1 calc R . .
C15 C 0.3944(5) 0.2116(4) 0.0768(4) 0.0579(13) Uani 1 1 d . . .
H15A H 0.3258 0.1728 0.0939 0.070 Uiso 1 1 calc R . .
C16 C 0.5344(4) 0.2271(3) 0.1498(3) 0.0452(11) Uani 1 1 d . . .
C21 C 0.9369(4) 0.3794(3) 0.2001(3) 0.0347(10) Uani 1 1 d . . .
C22 C 0.9045(5) 0.4788(3) 0.1809(3) 0.0477(11) Uani 1 1 d . . .
C23 C 0.9943(6) 0.5440(4) 0.1541(3) 0.0650(14) Uani 1 1 d . . .
H23A H 0.9669 0.6091 0.1405 0.078 Uiso 1 1 calc R . .
C24 C 1.1275(6) 0.5097(5) 0.1479(4) 0.0713(17) Uani 1 1 d . . .
H24A H 1.1912 0.5525 0.1303 0.086 Uiso 1 1 calc R . .
C25 C 1.1667(5) 0.4138(4) 0.1673(4) 0.0632(14) Uani 1 1 d . . .
H25A H 1.2566 0.3914 0.1633 0.076 Uiso 1 1 calc R . .
C26 C 1.0722(4) 0.3510(3) 0.1925(3) 0.0433(11) Uani 1 1 d . . .
C31 C 0.7889(4) 0.3589(3) 0.3498(3) 0.0322(9) Uani 1 1 d . . .
C32 C 0.8986(4) 0.3569(3) 0.4517(3) 0.0452(11) Uani 1 1 d . . .
C33 C 0.8903(5) 0.4008(3) 0.5428(3) 0.0555(12) Uani 1 1 d . . .
H33A H 0.9698 0.3977 0.6078 0.067 Uiso 1 1 calc R . .
C34 C 0.7615(5) 0.4493(3) 0.5354(4) 0.0578(13) Uani 1 1 d . . .
H34A H 0.7521 0.4790 0.5960 0.069 Uiso 1 1 calc R . .
C35 C 0.6462(5) 0.4538(3) 0.4381(4) 0.0558(12) Uani 1 1 d . . .
H35A H 0.5584 0.4863 0.4327 0.067 Uiso 1 1 calc R . .
C36 C 0.6612(4) 0.4100(3) 0.3483(3) 0.0413(10) 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'
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
C21 P1 C11 105.82(17) . . ?
C21 P1 C31 99.60(17) . . ?
C11 P1 C31 104.33(16) . . ?
C16 C11 C12 113.7(4) . . ?
C16 C11 P1 116.1(3) . . ?
C12 C11 P1 129.9(3) . . ?
F12 C12 C13 116.9(4) . . ?
F12 C12 C11 119.2(3) . . ?
C13 C12 C11 123.9(4) . . ?
C14 C13 C12 118.6(4) . . ?
C13 C14 C15 120.9(4) . . ?
C16 C15 C14 117.8(4) . . ?
C15 C16 F16 118.2(4) . . ?
C15 C16 C11 125.0(4) . . ?
F16 C16 C11 116.8(3) . . ?
C26 C21 C22 114.4(4) . . ?
C26 C21 P1 119.0(3) . . ?
C22 C21 P1 126.5(3) . . ?
F22 C22 C23 117.8(4) . . ?
F22 C22 C21 117.9(4) . . ?
C23 C22 C21 124.3(4) . . ?
C22 C23 C24 117.7(5) . . ?
C25 C24 C23 120.9(5) . . ?
C24 C25 C26 119.3(5) . . ?
F26 C26 C25 118.4(4) . . ?
F26 C26 C21 118.2(4) . . ?
C25 C26 C21 123.4(4) . . ?
C32 C31 C36 112.6(3) . . ?
C32 C31 P1 117.3(3) . . ?
C36 C31 P1 130.0(3) . . ?
F32 C32 C33 118.0(4) . . ?
F32 C32 C31 116.0(3) . . ?
C33 C32 C31 126.0(4) . . ?
C34 C33 C32 118.2(4) . . ?
C33 C34 C35 119.8(4) . . ?
C34 C35 C36 119.8(4) . . ?
F36 C36 C35 117.6(3) . . ?
F36 C36 C31 118.8(3) . . ?
C35 C36 C31 123.6(4) . . ?
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 C21 1.837(4) . ?
P1 C11 1.841(4) . ?
P1 C31 1.851(4) . ?
F12 C12 1.357(4) . ?
F16 C16 1.370(5) . ?
F22 C22 1.358(5) . ?
F26 C26 1.368(5) . ?
F32 C32 1.362(4) . ?
F36 C36 1.359(4) . ?
C11 C16 1.389(5) . ?
C11 C12 1.392(5) . ?
C12 C13 1.381(6) . ?
C13 C14 1.364(6) . ?
C14 C15 1.386(6) . ?
C15 C16 1.368(6) . ?
C21 C26 1.386(5) . ?
C21 C22 1.399(6) . ?
C22 C23 1.368(6) . ?
C23 C24 1.385(7) . ?
C24 C25 1.366(7) . ?
C25 C26 1.369(6) . ?
C31 C32 1.392(5) . ?
C31 C36 1.400(5) . ?
C32 C33 1.373(6) . ?
C33 C34 1.371(6) . ?
C34 C35 1.375(6) . ?
C35 C36 1.382(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10452943
2 PubChem 15876355
