#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:17:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178843 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/97/4109706.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_4109706
loop_
_publ_author_name
'Alex S. Ionkin'
'William J. Marshall'
'Brian M. Fish'
'Matthew F. Schiffhauer'
'Fredric Davidson'
_publ_section_title
;
 A Stabilized β-Oxaphosphoniumbetaine: An Elusive Zwitterion
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9210
_journal_page_last               9215
_journal_paper_doi               10.1021/ja071644a
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C14 H27 F6 O2 P'
_chemical_formula_weight         372.33
_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                 114.995(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.693(2)
_cell_length_b                   23.126(6)
_cell_length_c                   9.831(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1791.3(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33040
_diffrn_reflns_theta_full        27.23
_diffrn_reflns_theta_max         27.23
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       ireg.plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0403
_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)+(0.0461P)²+0.6870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2848
_reflns_number_total             3986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071644asi20070412_015510_5.cif
_cod_data_source_block           07006
_cod_original_cell_volume        1791.2(8)
_cod_database_code               4109706
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
P1 P 1.31397(6) 0.10789(2) 0.80251(5) 0.02122(13) Uani 1 1 d .
O1 O 1.65063(16) 0.10075(5) 1.09474(14) 0.0286(3) Uani 1 1 d .
F1 F 1.80543(16) 0.18772(6) 1.00417(15) 0.0475(4) Uani 1 1 d .
C1 C 1.3028(2) 0.05000(8) 0.9188(2) 0.0273(4) Uani 1 1 d .
H1B H 1.2465 0.0632 0.9786 0.041 Uiso 1 1 calc R
H1C H 1.4155 0.0374 0.9833 0.041 Uiso 1 1 calc R
H1D H 1.2404 0.0184 0.8568 0.041 Uiso 1 1 calc R
C2 C 1.4476(3) 0.16736(8) 0.9105(2) 0.0249(4) Uani 1 1 d .
F2 F 1.67993(16) 0.25421(5) 1.07092(14) 0.0446(3) Uani 1 1 d .
F3 F 1.85724(15) 0.19753(5) 1.23606(14) 0.0465(4) Uani 1 1 d .
C3 C 1.5896(2) 0.15439(8) 1.07328(19) 0.0239(4) Uani 1 1 d .
F4 F 1.46267(19) 0.22393(6) 1.18309(16) 0.0543(4) Uani 1 1 d .
C4 C 1.7330(3) 0.19890(9) 1.0973(2) 0.0321(5) Uani 1 1 d .
F5 F 1.62581(17) 0.15910(7) 1.32896(13) 0.0523(4) Uani 1 1 d .
C5 C 1.5159(3) 0.16901(9) 1.1879(2) 0.0326(5) Uani 1 1 d .
F6 F 1.37929(17) 0.13627(6) 1.16370(14) 0.0483(4) Uani 1 1 d .
C6 C 1.4049(2) 0.07780(9) 0.6769(2) 0.0280(4) Uani 1 1 d .
C7 C 1.3824(4) 0.11899(11) 0.5485(3) 0.0500(6) Uani 1 1 d .
H7A H 1.4397 0.1036 0.4917 0.075 Uiso 1 1 calc R
H7B H 1.4296 0.1560 0.5887 0.075 Uiso 1 1 calc R
H7C H 1.2637 0.1232 0.4844 0.075 Uiso 1 1 calc R
C8 C 1.5946(3) 0.06679(11) 0.7712(2) 0.0445(6) Uani 1 1 d .
H8A H 1.6418 0.0479 0.7106 0.067 Uiso 1 1 calc R
H8B H 1.6091 0.0426 0.8551 0.067 Uiso 1 1 calc R
H8C H 1.6516 0.1030 0.8068 0.067 Uiso 1 1 calc R
C9 C 1.3197(3) 0.01992(11) 0.6106(3) 0.0516(7) Uani 1 1 d .
H9A H 1.3685 0.0045 0.5470 0.077 Uiso 1 1 calc R
H9B H 1.2003 0.0259 0.5528 0.077 Uiso 1 1 calc R
H9C H 1.3371 -0.0068 0.6905 0.077 Uiso 1 1 calc R
C10 C 1.0967(2) 0.13839(8) 0.7058(2) 0.0262(4) Uani 1 1 d .
C11 C 1.0375(3) 0.15587(11) 0.8267(2) 0.0401(5) Uani 1 1 d .
H11A H 0.9280 0.1739 0.7800 0.060 Uiso 1 1 calc R
H11B H 1.1174 0.1825 0.8953 0.060 Uiso 1 1 calc R
H11C H 1.0300 0.1221 0.8803 0.060 Uiso 1 1 calc R
C12 C 0.9739(3) 0.09284(10) 0.6038(2) 0.0404(5) Uani 1 1 d .
H12A H 0.8594 0.1066 0.5696 0.061 Uiso 1 1 calc R
H12B H 0.9864 0.0576 0.6589 0.061 Uiso 1 1 calc R
H12C H 0.9989 0.0858 0.5190 0.061 Uiso 1 1 calc R
C13 C 1.0927(3) 0.19272(10) 0.6136(3) 0.0429(6) Uani 1 1 d .
H13A H 0.9792 0.2078 0.5681 0.064 Uiso 1 1 calc R
H13B H 1.1287 0.1828 0.5368 0.064 Uiso 1 1 calc R
H13C H 1.1676 0.2214 0.6785 0.064 Uiso 1 1 calc R
O21 O 0.95400(19) 0.06033(7) 1.26121(16) 0.0357(4) Uani 1 1 d .
H21 H 0.852(4) 0.0788(13) 1.209(3) 0.073(9) Uiso 1 1 d .
C22 C 1.0409(3) 0.06276(11) 1.1695(3) 0.0451(6) Uani 1 1 d .
H22" H 1.0715 0.1021 1.1616 0.068 Uiso 1 1 calc R
H22' H 0.9690 0.0483 1.0714 0.068 Uiso 1 1 calc R
H22 H 1.1416 0.0395 1.2125 0.068 Uiso 1 1 calc R
H2 H 1.370(3) 0.1978(9) 0.913(2) 0.037(6) Uiso 1 1 d .
H2' H 1.501(3) 0.1805(8) 0.851(2) 0.028(5) Uiso 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'
O O 0.0106 0.0060 '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
C1 P1 C2 112.68(9)
C1 P1 C10 107.05(9)
C2 P1 C10 105.76(9)
C1 P1 C6 107.29(9)
C2 P1 C6 108.88(10)
C10 P1 C6 115.31(9)
C3 C2 P1 118.58(13)
O1 C3 C5 110.34(15)
O1 C3 C4 110.63(16)
C5 C3 C4 107.22(15)
O1 C3 C2 115.17(15)
C5 C3 C2 107.98(16)
C4 C3 C2 105.09(15)
F3 C4 F1 106.47(17)
F3 C4 F2 106.41(16)
F1 C4 F2 105.89(17)
F3 C4 C3 112.93(17)
F1 C4 C3 110.30(16)
F2 C4 C3 114.30(16)
F5 C5 F6 106.25(17)
F5 C5 F4 106.51(16)
F6 C5 F4 105.13(17)
F5 C5 C3 112.63(17)
F6 C5 C3 110.75(16)
F4 C5 C3 114.93(17)
C7 C6 C8 109.44(19)
C7 C6 C9 108.82(19)
C8 C6 C9 108.32(19)
C7 C6 P1 111.94(15)
C8 C6 P1 108.12(13)
C9 C6 P1 110.13(14)
C12 C10 C11 108.57(17)
C12 C10 C13 109.83(17)
C11 C10 C13 107.99(18)
C12 C10 P1 110.52(14)
C11 C10 P1 107.72(12)
C13 C10 P1 112.09(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C1 1.7897(19)
P1 C2 1.8236(19)
P1 C10 1.8578(19)
P1 C6 1.860(2)
O1 C3 1.331(2)
F1 C4 1.337(2)
C2 C3 1.583(2)
F2 C4 1.347(2)
F3 C4 1.335(2)
C3 C5 1.551(3)
C3 C4 1.556(3)
F4 C5 1.346(2)
F5 C5 1.330(2)
C5 F6 1.342(2)
C6 C7 1.526(3)
C6 C8 1.533(3)
C6 C9 1.535(3)
C10 C12 1.533(3)
C10 C11 1.536(3)
C10 C13 1.541(3)
O21 C22 1.401(3)
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
C1 P1 C2 C3 23.57(19)
C10 P1 C2 C3 140.19(15)
C6 P1 C2 C3 -95.34(17)
P1 C2 C3 O1 28.1(2)
P1 C2 C3 C5 -95.67(18)
P1 C2 C3 C4 150.14(15)
O1 C3 C4 F3 -61.0(2)
C5 C3 C4 F3 59.3(2)
C2 C3 C4 F3 174.07(16)
O1 C3 C4 F1 58.0(2)
C5 C3 C4 F1 178.34(15)
C2 C3 C4 F1 -66.9(2)
O1 C3 C4 F2 177.13(16)
C5 C3 C4 F2 -62.5(2)
C2 C3 C4 F2 52.2(2)
O1 C3 C5 F5 52.9(2)
C4 C3 C5 F5 -67.7(2)
C2 C3 C5 F5 179.54(16)
O1 C3 C5 F6 -66.0(2)
C4 C3 C5 F6 173.50(16)
C2 C3 C5 F6 60.7(2)
O1 C3 C5 F4 175.10(15)
C4 C3 C5 F4 54.5(2)
C2 C3 C5 F4 -58.2(2)
C1 P1 C6 C7 166.57(15)
C2 P1 C6 C7 -71.21(17)
C10 P1 C6 C7 47.43(18)
C1 P1 C6 C8 -72.82(17)
C2 P1 C6 C8 49.41(17)
C10 P1 C6 C8 168.04(15)
C1 P1 C6 C9 45.36(17)
C2 P1 C6 C9 167.58(15)
C10 P1 C6 C9 -73.78(18)
C1 P1 C10 C12 -62.76(16)
C2 P1 C10 C12 176.86(15)
C6 P1 C10 C12 56.51(17)
C1 P1 C10 C11 55.70(16)
C2 P1 C10 C11 -64.67(16)
C6 P1 C10 C11 174.97(14)
C1 P1 C10 C13 174.36(15)
C2 P1 C10 C13 53.99(16)
C6 P1 C10 C13 -66.37(17)
