#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/16/2211692.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2211692
loop_
_publ_author_name
'Klausmeyer, Kevin K.'
'Hung, Fernando'
_publ_section_title
;
 2-(Diphenylphosphinoylmethyl)pyridinium tetrafluoroborate
;
_journal_coeditor_code           YM2033
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5560
_journal_page_last               o5562
_journal_paper_doi               10.1107/S1600536806047179
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H17 N O P +, B F4 -'
_chemical_formula_moiety         'C18 H17 N O P +, B F4 -'
_chemical_formula_sum            'C18 H17 B F4 N O P'
_chemical_formula_weight         381.11
_chemical_name_systematic
;
2-(Diphenylphosphinoylmethyl)pyridinium tetrafluoroborate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.314(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.7528(15)
_cell_length_b                   13.9287(17)
_cell_length_c                   15.661(2)
_cell_measurement_reflns_used    4891
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.9
_cell_measurement_theta_min      2.3
_cell_volume                     3638.7(7)
_computing_cell_refinement       APEX-2
_computing_data_collection       'APEX-2 (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14958
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         29.0
_diffrn_reflns_theta_min         1.9
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.57
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0684P)²+4.7739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.129
_refine_ls_wR_factor_ref         0.138
_reflns_number_gt                3915
_reflns_number_total             4726
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ym2033.cif
_cod_data_source_block           I
_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.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2211692
_cod_database_fobs_code          2211692
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
P P1 0.12999(2) 0.13722(3) 0.21304(3) 0.01466(12) Uani d . 1
C C1 0.14074(10) 0.14601(12) 0.33002(11) 0.0178(3) Uani d . 1
H H1A 0.1901 0.1822 0.3489 0.021 Uiso calc R 1
H H1B 0.0945 0.1813 0.3496 0.021 Uiso calc R 1
C C3 0.21554(10) 0.00480(13) 0.40151(11) 0.0208(4) Uani d . 1
H H3 0.2648 0.0388 0.4028 0.025 Uiso calc R 1
C C2 0.14494(9) 0.04814(12) 0.36900(10) 0.0165(3) Uani d . 1
C C5 0.14205(11) -0.13773(14) 0.43108(13) 0.0249(4) Uani d . 1
H H5 0.1405 -0.2018 0.4518 0.030 Uiso calc R 1
C C4 0.21426(10) -0.08853(14) 0.43224(12) 0.0237(4) Uani d . 1
H H4 0.2627 -0.1188 0.4541 0.028 Uiso calc R 1
C C6 0.07283(11) -0.09199(14) 0.39939(13) 0.0259(4) Uani d . 1
H H6 0.0228 -0.1242 0.3987 0.031 Uiso calc R 1
C C7 0.10845(9) 0.25679(12) 0.17494(10) 0.0159(3) Uani d . 1
C C12 0.05666(9) 0.26688(13) 0.09984(11) 0.0198(3) Uani d . 1
H H12 0.0335 0.2117 0.0717 0.024 Uiso calc R 1
C C11 0.03931(10) 0.35780(14) 0.06669(12) 0.0257(4) Uani d . 1
H H11 0.0046 0.3647 0.0156 0.031 Uiso calc R 1
C C8 0.14092(10) 0.33822(13) 0.21700(11) 0.0215(4) Uani d . 1
H H8 0.1754 0.3319 0.2684 0.026 Uiso calc R 1
C C9 0.12241(11) 0.42880(13) 0.18318(12) 0.0238(4) Uani d . 1
H H9 0.1441 0.4844 0.2118 0.029 Uiso calc R 1
C C10 0.07242(10) 0.43828(14) 0.10780(13) 0.0254(4) Uani d . 1
H H10 0.0609 0.5002 0.0844 0.031 Uiso calc R 1
C C13 0.22466(9) 0.09971(12) 0.17851(11) 0.0174(3) Uani d . 1
C C18 0.29336(10) 0.15760(14) 0.19020(13) 0.0246(4) Uani d . 1
H H18 0.2914 0.2177 0.2186 0.030 Uiso calc R 1
C C15 0.29886(13) -0.01938(16) 0.10691(13) 0.0307(4) Uani d . 1
H H15 0.3011 -0.0795 0.0786 0.037 Uiso calc R 1
C C14 0.22759(11) 0.01126(13) 0.13754(11) 0.0224(4) Uani d . 1
H H14 0.1812 -0.0281 0.1305 0.027 Uiso calc R 1
C C16 0.36621(13) 0.03805(17) 0.11788(15) 0.0368(5) Uani d . 1
H H16 0.4145 0.0172 0.0964 0.044 Uiso calc R 1
C C17 0.36453(11) 0.12621(16) 0.15988(16) 0.0348(5) Uani d . 1
H H17 0.4115 0.1646 0.1678 0.042 Uiso calc R 1
O O1 0.06584(7) 0.06754(9) 0.18240(8) 0.0224(3) Uani d . 1
B B1 0.12519(12) 0.75309(16) 0.08558(16) 0.0273(5) Uani d . 1
F F1 0.10055(8) 0.82067(11) 0.02406(9) 0.0421(3) Uani d . 1
F F2 0.19457(8) 0.78232(10) 0.13255(10) 0.0486(4) Uani d . 1
F F3 0.13956(10) 0.66594(12) 0.04854(14) 0.0736(6) Uani d . 1
F F4 0.06365(10) 0.74127(16) 0.13657(14) 0.0825(7) Uani d . 1
N N1 0.07583(8) -0.00194(11) 0.36942(10) 0.0203(3) Uani d . 1
H H1C 0.0270(16) 0.0281(18) 0.3457(16) 0.040(7) Uiso d . 1
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'
B B 0.0013 0.0007 '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_publ_flag
O1 P1 C7 112.31(7) y
O1 P1 C13 110.04(8) y
C7 P1 C13 108.97(8) y
O1 P1 C1 111.51(8) y
C7 P1 C1 105.61(8) y
C13 P1 C1 108.22(8) y
C2 C1 P1 110.20(12) ?
C2 C1 H1A 109.6 ?
P1 C1 H1A 109.6 ?
C2 C1 H1B 109.6 ?
P1 C1 H1B 109.6 ?
H1A C1 H1B 108.1 ?
C2 C3 C4 119.79(16) ?
C2 C3 H3 120.1 ?
C4 C3 H3 120.1 ?
N1 C2 C3 118.47(16) ?
N1 C2 C1 117.72(14) ?
C3 C2 C1 123.76(15) ?
C6 C5 C4 118.72(17) ?
C6 C5 H5 120.6 ?
C4 C5 H5 120.6 ?
C3 C4 C5 119.95(16) ?
C3 C4 H4 120.0 ?
C5 C4 H4 120.0 ?
N1 C6 C5 120.12(16) ?
N1 C6 H6 119.9 ?
C5 C6 H6 119.9 ?
C8 C7 C12 119.86(16) ?
C8 C7 P1 122.65(12) ?
C12 C7 P1 117.49(13) ?
C11 C12 C7 119.77(16) ?
C11 C12 H12 120.1 ?
C7 C12 H12 120.1 ?
C10 C11 C12 120.26(16) ?
C10 C11 H11 119.9 ?
C12 C11 H11 119.9 ?
C9 C8 C7 119.57(16) ?
C9 C8 H8 120.2 ?
C7 C8 H8 120.2 ?
C10 C9 C8 120.33(17) ?
C10 C9 H9 119.8 ?
C8 C9 H9 119.8 ?
C11 C10 C9 120.19(17) ?
C11 C10 H10 119.9 ?
C9 C10 H10 119.9 ?
C14 C13 C18 120.35(16) ?
C14 C13 P1 117.71(13) ?
C18 C13 P1 121.93(14) ?
C17 C18 C13 119.49(19) ?
C17 C18 H18 120.3 ?
C13 C18 H18 120.3 ?
C16 C15 C14 119.7(2) ?
C16 C15 H15 120.1 ?
C14 C15 H15 120.1 ?
C13 C14 C15 119.83(18) ?
C13 C14 H14 120.1 ?
C15 C14 H14 120.1 ?
C15 C16 C17 121.13(18) ?
C15 C16 H16 119.4 ?
C17 C16 H16 119.4 ?
C18 C17 C16 119.48(19) ?
C18 C17 H17 120.3 ?
C16 C17 H17 120.3 ?
F4 B1 F3 108.0(2) ?
F4 B1 F2 111.5(2) ?
F3 B1 F2 108.28(17) ?
F4 B1 F1 107.19(17) ?
F3 B1 F1 111.1(2) ?
F2 B1 F1 110.70(18) ?
C6 N1 C2 122.94(15) ?
C6 N1 H1C 118.9(16) ?
C2 N1 H1C 118.1(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 1.4939(12) y
P1 C7 1.7946(17) y
P1 C13 1.8000(17) y
P1 C1 1.8283(18) y
C1 C2 1.493(2) ?
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C3 C2 1.382(2) ?
C3 C4 1.387(3) ?
C3 H3 0.9500 ?
C2 N1 1.352(2) ?
C5 C6 1.375(3) ?
C5 C4 1.389(3) ?
C5 H5 0.9500 ?
C4 H4 0.9500 ?
C6 N1 1.342(2) ?
C6 H6 0.9500 ?
C7 C8 1.396(2) ?
C7 C12 1.402(2) ?
C12 C11 1.389(3) ?
C12 H12 0.9500 ?
C11 C10 1.383(3) ?
C11 H11 0.9500 ?
C8 C9 1.392(3) ?
C8 H8 0.9500 ?
C9 C10 1.389(3) ?
C9 H9 0.9500 ?
C10 H10 0.9500 ?
C13 C14 1.392(3) ?
C13 C18 1.403(2) ?
C18 C17 1.394(3) ?
C18 H18 0.9500 ?
C15 C16 1.381(3) ?
C15 C14 1.394(3) ?
C15 H15 0.9500 ?
C14 H14 0.9500 ?
C16 C17 1.394(3) ?
C16 H16 0.9500 ?
C17 H17 0.9500 ?
B1 F4 1.371(3) ?
B1 F3 1.376(3) ?
B1 F2 1.378(2) ?
B1 F1 1.382(3) ?
N1 H1C 0.96(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1C O1 2 0.96(3) 1.67(3) 2.6212(18) 169(2) y
C1 H1A F2 4_545 0.99 2.38 3.356(2) 168.9 y
C18 H18 F2 4_545 0.95 2.49 3.265(3) 138.8 y
C3 H3 F3 4_545 0.95 2.46 3.345(2) 154.8 y
C6 H6 F4 2_545 0.95 2.40 3.271(3) 152.1 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125761
