#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:55:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180202 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/96/7109631.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_7109631
loop_
_publ_author_name
'Jian Zheng'
'Ji Cai'
'Jin-Hong Lin'
'Yong Guo'
'Ji-Chang Xiao'
_publ_section_title
;
 Synthesis and decarboxylative Wittig reaction of difluoromethylene
 phosphobetaine
;
_journal_name_full               Chem.Commun.
_journal_page_first              7513
_journal_paper_doi               10.1039/c3cc44271c
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C20 H15 F2 O2 P'
_chemical_formula_weight         356.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.014(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3883(14)
_cell_length_b                   10.0280(11)
_cell_length_c                   13.0620(15)
_cell_measurement_reflns_used    1799
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.257
_cell_measurement_theta_min      4.656
_cell_volume                     1620.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9528
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09179
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0438
_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)+(0.0622P)²+0.0885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                2423
_reflns_number_total             3172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44271c.txt
_cod_data_source_block           cd212473
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7109631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.90820(4) 0.22131(5) 0.28732(4) 0.02967(17) Uani 1 1 d .
F1 F 0.93581(10) -0.02776(13) 0.34307(10) 0.0525(4) Uani 1 1 d .
F2 F 1.03904(11) 0.11374(14) 0.42695(9) 0.0522(4) Uani 1 1 d .
O1 O 1.13700(16) -0.05910(19) 0.27967(15) 0.0747(6) Uani 1 1 d .
O2 O 1.11630(14) 0.13860(17) 0.20445(13) 0.0583(5) Uani 1 1 d .
C1 C 0.99949(16) 0.0804(2) 0.33069(15) 0.0357(5) Uani 1 1 d .
C2 C 1.09547(17) 0.0491(2) 0.26392(17) 0.0398(5) Uani 1 1 d .
C3 C 0.87283(16) 0.2082(2) 0.15353(15) 0.0319(5) Uani 1 1 d .
C4 C 0.87612(18) 0.0873(2) 0.10251(16) 0.0424(5) Uani 1 1 d .
H4 H 0.8993 0.0108 0.1375 0.051 Uiso 1 1 calc R
C5 C 0.84497(19) 0.0805(3) -0.00038(17) 0.0491(6) Uani 1 1 d .
H5 H 0.8478 -0.0006 -0.0348 0.059 Uiso 1 1 calc R
C6 C 0.81005(19) 0.1924(3) -0.05200(17) 0.0508(6) Uani 1 1 d .
H6 H 0.7895 0.1872 -0.1214 0.061 Uiso 1 1 calc R
C7 C 0.80514(19) 0.3121(3) -0.00181(18) 0.0507(6) Uani 1 1 d .
H7 H 0.7799 0.3876 -0.0369 0.061 Uiso 1 1 calc R
C8 C 0.83753(17) 0.3209(2) 0.10054(16) 0.0413(5) Uani 1 1 d .
H8 H 0.8357 0.4027 0.1340 0.050 Uiso 1 1 calc R
C9 C 0.78899(16) 0.2038(2) 0.35889(15) 0.0319(5) Uani 1 1 d .
C10 C 0.68868(17) 0.2310(2) 0.31312(16) 0.0405(5) Uani 1 1 d .
H10 H 0.6816 0.2506 0.2435 0.049 Uiso 1 1 calc R
C11 C 0.59865(18) 0.2292(2) 0.37110(19) 0.0488(6) Uani 1 1 d .
H11 H 0.5306 0.2462 0.3404 0.059 Uiso 1 1 calc R
C12 C 0.60960(19) 0.2022(2) 0.47379(19) 0.0501(6) Uani 1 1 d .
H12 H 0.5489 0.2027 0.5128 0.060 Uiso 1 1 calc R
C13 C 0.70879(19) 0.1746(2) 0.51970(17) 0.0487(6) Uani 1 1 d .
H13 H 0.7154 0.1565 0.5896 0.058 Uiso 1 1 calc R
C14 C 0.79840(17) 0.1738(2) 0.46255(15) 0.0411(5) Uani 1 1 d .
H14 H 0.8657 0.1531 0.4934 0.049 Uiso 1 1 calc R
C15 C 0.96709(16) 0.3806(2) 0.31732(14) 0.0322(5) Uani 1 1 d .
C16 C 0.91079(17) 0.4697(2) 0.37557(16) 0.0395(5) Uani 1 1 d .
H16 H 0.8460 0.4445 0.4028 0.047 Uiso 1 1 calc R
C17 C 0.9517(2) 0.5962(2) 0.39282(18) 0.0493(6) Uani 1 1 d .
H17 H 0.9139 0.6570 0.4311 0.059 Uiso 1 1 calc R
C18 C 1.0470(2) 0.6321(3) 0.35399(19) 0.0542(7) Uani 1 1 d .
H18 H 1.0735 0.7179 0.3650 0.065 Uiso 1 1 calc R
C19 C 1.1043(2) 0.5434(3) 0.2988(2) 0.0556(7) Uani 1 1 d .
H19 H 1.1705 0.5686 0.2744 0.067 Uiso 1 1 calc R
C20 C 1.06520(18) 0.4175(2) 0.27921(18) 0.0461(6) Uani 1 1 d .
H20 H 1.1039 0.3577 0.2409 0.055 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
C3 P1 C15 110.89(9)
C3 P1 C9 109.64(9)
C15 P1 C9 108.04(9)
C3 P1 C1 110.66(9)
C15 P1 C1 111.89(9)
C9 P1 C1 105.53(9)
F1 C1 F2 105.57(16)
F1 C1 C2 111.99(18)
F2 C1 C2 108.67(16)
F1 C1 P1 107.03(13)
F2 C1 P1 105.95(13)
C2 C1 P1 116.89(15)
O1 C2 O2 131.4(2)
O1 C2 C1 114.8(2)
O2 C2 C1 113.80(19)
C8 C3 C4 119.40(19)
C8 C3 P1 118.95(16)
C4 C3 P1 121.60(16)
C5 C4 C3 119.8(2)
C5 C4 H4 120.1
C3 C4 H4 120.1
C6 C5 C4 120.3(2)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C7 120.2(2)
C5 C6 H6 119.9
C7 C6 H6 119.9
C6 C7 C8 120.1(2)
C6 C7 H7 119.9
C8 C7 H7 119.9
C7 C8 C3 120.0(2)
C7 C8 H8 120.0
C3 C8 H8 120.0
C10 C9 C14 119.64(18)
C10 C9 P1 120.12(15)
C14 C9 P1 120.01(16)
C9 C10 C11 119.7(2)
C9 C10 H10 120.1
C11 C10 H10 120.2
C12 C11 C10 119.9(2)
C12 C11 H11 120.0
C10 C11 H11 120.0
C13 C12 C11 120.7(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 119.8(2)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C9 120.1(2)
C13 C14 H14 119.9
C9 C14 H14 119.9
C16 C15 C20 120.0(2)
C16 C15 P1 118.98(16)
C20 C15 P1 120.93(16)
C17 C16 C15 119.4(2)
C17 C16 H16 120.3
C15 C16 H16 120.3
C18 C17 C16 120.1(2)
C18 C17 H17 120.0
C16 C17 H17 120.0
C17 C18 C19 120.7(2)
C17 C18 H18 119.6
C19 C18 H18 119.6
C18 C19 C20 120.6(2)
C18 C19 H19 119.7
C20 C19 H19 119.7
C19 C20 C15 119.1(2)
C19 C20 H20 120.5
C15 C20 H20 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C3 1.784(2)
P1 C15 1.791(2)
P1 C9 1.7976(19)
P1 C1 1.878(2)
F1 C1 1.356(2)
F2 C1 1.367(2)
O1 C2 1.213(3)
O2 C2 1.224(3)
C1 C2 1.544(3)
C3 C8 1.385(3)
C3 C4 1.385(3)
C4 C5 1.380(3)
C4 H4 0.9300
C5 C6 1.367(3)
C5 H5 0.9300
C6 C7 1.371(3)
C6 H6 0.9300
C7 C8 1.378(3)
C7 H7 0.9300
C8 H8 0.9300
C9 C10 1.378(3)
C9 C14 1.386(3)
C10 C11 1.381(3)
C10 H10 0.9300
C11 C12 1.368(3)
C11 H11 0.9300
C12 C13 1.367(3)
C12 H12 0.9300
C13 C14 1.370(3)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.386(3)
C15 C20 1.388(3)
C16 C17 1.380(3)
C16 H16 0.9300
C17 C18 1.357(4)
C17 H17 0.9300
C18 C19 1.367(4)
C18 H18 0.9300
C19 C20 1.371(3)
C19 H19 0.9300
C20 H20 0.9300
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
C3 P1 C1 F1 -79.69(15)
C15 P1 C1 F1 156.10(13)
C9 P1 C1 F1 38.84(15)
C3 P1 C1 F2 168.01(12)
C15 P1 C1 F2 43.80(16)
C9 P1 C1 F2 -73.46(15)
C3 P1 C1 C2 46.79(18)
C15 P1 C1 C2 -77.42(17)
C9 P1 C1 C2 165.32(15)
F1 C1 C2 O1 -39.7(3)
F2 C1 C2 O1 76.6(3)
P1 C1 C2 O1 -163.66(19)
F1 C1 C2 O2 140.5(2)
F2 C1 C2 O2 -103.2(2)
P1 C1 C2 O2 16.6(3)
C15 P1 C3 C8 -34.06(19)
C9 P1 C3 C8 85.16(18)
C1 P1 C3 C8 -158.84(16)
C15 P1 C3 C4 148.33(17)
C9 P1 C3 C4 -92.45(19)
C1 P1 C3 C4 23.5(2)
C8 C3 C4 C5 0.4(3)
P1 C3 C4 C5 178.02(17)
C3 C4 C5 C6 -0.5(3)
C4 C5 C6 C7 -0.3(4)
C5 C6 C7 C8 1.3(4)
C6 C7 C8 C3 -1.4(3)
C4 C3 C8 C7 0.6(3)
P1 C3 C8 C7 -177.10(17)
C3 P1 C9 C10 -23.2(2)
C15 P1 C9 C10 97.73(18)
C1 P1 C9 C10 -142.44(17)
C3 P1 C9 C14 162.21(17)
C15 P1 C9 C14 -76.83(19)
C1 P1 C9 C14 43.00(19)
C14 C9 C10 C11 0.5(3)
P1 C9 C10 C11 -174.10(17)
C9 C10 C11 C12 0.9(3)
C10 C11 C12 C13 -1.2(4)
C11 C12 C13 C14 0.0(4)
C12 C13 C14 C9 1.4(4)
C10 C9 C14 C13 -1.7(3)
P1 C9 C14 C13 172.91(18)
C3 P1 C15 C16 112.14(17)
C9 P1 C15 C16 -8.03(19)
C1 P1 C15 C16 -123.78(17)
C3 P1 C15 C20 -64.88(19)
C9 P1 C15 C20 174.95(17)
C1 P1 C15 C20 59.2(2)
C20 C15 C16 C17 1.8(3)
P1 C15 C16 C17 -175.29(17)
C15 C16 C17 C18 -0.8(3)
C16 C17 C18 C19 -1.0(4)
C17 C18 C19 C20 1.8(4)
C18 C19 C20 C15 -0.9(4)
C16 C15 C20 C19 -0.9(3)
P1 C15 C20 C19 176.06(19)
