#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/97/4109702.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_4109702
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            'C12 H22 F3 O P'
_chemical_formula_weight         270.27
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 102.946(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.496(3)
_cell_length_b                   20.619(7)
_cell_length_c                   8.291(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1415.5(9)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9898
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       hex.plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0520
_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)+(0.0921P)²+0.4111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                2946
_reflns_number_total             3243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071644asi20070412_015510_1.cif
_cod_data_source_block           07086
_cod_database_code               4109702
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'
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 0.98342(6) 0.34986(2) 0.02569(6) 0.02555(16) Uani 1 1 d .
F1 F 0.5583(3) 0.46025(10) -0.2519(3) 0.0588(6) Uani 1 1 d .
O1 O 0.7928(3) 0.33181(11) -0.3502(2) 0.0411(5) Uani 1 1 d .
C1 C 0.9935(3) 0.26789(12) -0.0437(4) 0.0343(5) Uani 1 1 d .
H1A H 1.0097 0.2680 -0.1547 0.051 Uiso 1 1 calc R
H1B H 0.8944 0.2459 -0.0416 0.051 Uiso 1 1 calc R
H1C H 1.0819 0.2459 0.0279 0.051 Uiso 1 1 calc R
C2 C 0.8211(3) 0.39085(12) -0.0979(3) 0.0295(5) Uani 1 1 d .
H2A H 0.7770 0.4256 -0.0516 0.035 Uiso 1 1 calc R
F2 F 0.4796(3) 0.37979(12) -0.4029(4) 0.0794(9) Uani 1 1 d .
C3 C 0.7543(3) 0.37486(12) -0.2600(3) 0.0299(5) Uani 1 1 d .
F3 F 0.6401(4) 0.44905(17) -0.4708(4) 0.0993(12) Uani 1 1 d .
C4 C 0.6086(4) 0.41597(14) -0.3462(3) 0.0368(6) Uani 1 1 d .
C5 C 1.1774(3) 0.38761(13) 0.0099(3) 0.0335(5) Uani 1 1 d .
C6 C 1.3255(4) 0.34804(17) 0.0933(5) 0.0529(9) Uani 1 1 d .
H6A H 1.4199 0.3657 0.0641 0.079 Uiso 1 1 calc R
H6B H 1.3114 0.3038 0.0571 0.079 Uiso 1 1 calc R
H6C H 1.3381 0.3498 0.2112 0.079 Uiso 1 1 calc R
C7 C 1.1915(4) 0.45674(15) 0.0807(5) 0.0505(8) Uani 1 1 d .
H7A H 1.2759 0.4795 0.0444 0.076 Uiso 1 1 calc R
H7B H 1.2165 0.4548 0.1994 0.076 Uiso 1 1 calc R
H7C H 1.0910 0.4791 0.0427 0.076 Uiso 1 1 calc R
C8 C 1.1721(5) 0.3927(2) -0.1768(4) 0.0532(8) Uani 1 1 d .
H8A H 1.2679 0.4141 -0.1926 0.080 Uiso 1 1 calc R
H8B H 1.0787 0.4171 -0.2302 0.080 Uiso 1 1 calc R
H8C H 1.1666 0.3500 -0.2238 0.080 Uiso 1 1 calc R
C9 C 0.9452(4) 0.34651(13) 0.2371(3) 0.0323(5) Uani 1 1 d .
C10 C 1.0851(5) 0.3158(2) 0.3605(4) 0.0584(10) Uani 1 1 d .
H10A H 1.0526 0.3070 0.4620 0.088 Uiso 1 1 calc R
H10B H 1.1754 0.3450 0.3816 0.088 Uiso 1 1 calc R
H10C H 1.1156 0.2760 0.3157 0.088 Uiso 1 1 calc R
C11 C 0.9072(7) 0.41352(19) 0.2962(5) 0.0647(11) Uani 1 1 d .
H11A H 0.8889 0.4103 0.4061 0.097 Uiso 1 1 calc R
H11B H 0.8122 0.4304 0.2230 0.097 Uiso 1 1 calc R
H11C H 0.9966 0.4421 0.2969 0.097 Uiso 1 1 calc R
C12 C 0.7955(5) 0.3038(2) 0.2278(4) 0.0585(10) Uani 1 1 d .
H12A H 0.7647 0.3048 0.3323 0.088 Uiso 1 1 calc R
H12B H 0.8199 0.2601 0.2025 0.088 Uiso 1 1 calc R
H12C H 0.7083 0.3199 0.1428 0.088 Uiso 1 1 calc R
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'
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
C2 P1 C1 110.93(12)
C2 P1 C5 110.73(12)
C1 P1 C5 105.40(13)
C2 P1 C9 106.92(13)
C1 P1 C9 107.42(13)
C5 P1 C9 115.42(13)
C3 C2 P1 123.86(19)
O1 C3 C2 130.4(2)
O1 C3 C4 113.8(2)
C2 C3 C4 115.8(2)
F3 C4 F2 108.2(3)
F3 C4 F1 104.7(3)
F2 C4 F1 104.2(3)
F3 C4 C3 111.5(3)
F2 C4 C3 111.8(2)
F1 C4 C3 115.8(2)
C6 C5 C7 109.6(3)
C6 C5 C8 109.0(3)
C7 C5 C8 107.7(3)
C6 C5 P1 113.5(2)
C7 C5 P1 110.9(2)
C8 C5 P1 105.9(2)
C10 C9 C11 110.5(3)
C10 C9 C12 108.0(3)
C11 C9 C12 107.6(3)
C10 C9 P1 112.1(2)
C11 C9 P1 111.4(2)
C12 C9 P1 107.02(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C2 1.741(2)
P1 C1 1.794(3)
P1 C5 1.853(3)
P1 C9 1.854(3)
F1 C4 1.333(4)
O1 C3 1.251(3)
C2 C3 1.377(4)
F2 C4 1.322(4)
C3 C4 1.538(4)
F3 C4 1.314(4)
C5 C6 1.529(4)
C5 C7 1.536(4)
C5 C8 1.542(4)
C9 C10 1.522(4)
C9 C11 1.525(4)
C9 C12 1.534(4)
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 -25.7(3)
C5 P1 C2 C3 91.0(2)
C9 P1 C2 C3 -142.5(2)
P1 C2 C3 O1 -1.5(4)
P1 C2 C3 C4 178.41(19)
O1 C3 C4 F3 -63.7(4)
C2 C3 C4 F3 116.3(3)
O1 C3 C4 F2 57.5(3)
C2 C3 C4 F2 -122.4(3)
O1 C3 C4 F1 176.7(3)
C2 C3 C4 F1 -3.3(4)
C2 P1 C5 C6 -171.0(2)
C1 P1 C5 C6 -50.9(3)
C9 P1 C5 C6 67.4(3)
C2 P1 C5 C7 65.1(2)
C1 P1 C5 C7 -174.9(2)
C9 P1 C5 C7 -56.5(2)
C2 P1 C5 C8 -51.4(2)
C1 P1 C5 C8 68.6(2)
C9 P1 C5 C8 -173.0(2)
C2 P1 C9 C10 -176.0(2)
C1 P1 C9 C10 64.9(3)
C5 P1 C9 C10 -52.3(3)
C2 P1 C9 C11 -51.6(3)
C1 P1 C9 C11 -170.7(3)
C5 P1 C9 C11 72.1(3)
C2 P1 C9 C12 65.8(2)
C1 P1 C9 C12 -53.3(3)
C5 P1 C9 C12 -170.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660364
