#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:05:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178420 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/41/4024191.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_4024191
loop_
_publ_author_name
'Jinhua Song'
'Hiroshi Yamataka'
'Zvi Rappoport'
_publ_section_title
;
 Dialkoxyphosphinyl-Substituted Enols of Carboxamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7605
_journal_page_last               7624
_journal_paper_doi               10.1021/jo0710679
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C12 H11 F5 N O6 P'
_chemical_formula_sum            'C12 H11 F5 N O6 P'
_chemical_formula_weight         391.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.2280(10)
_cell_angle_beta                 96.5510(10)
_cell_angle_gamma                104.6930(10)
_cell_formula_units_Z            2
_cell_length_a                   6.1721(4)
_cell_length_b                   8.3012(6)
_cell_length_c                   17.1703(12)
_cell_measurement_temperature    295(2)
_cell_volume                     825.66(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9478
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9519
_exptl_absorpt_correction_T_min  0.9336
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0480
_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)+(0.0703P)²+0.2741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                3335
_reflns_number_total             3583
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0710679-File002.cif
_cod_data_source_block           song12m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4024191
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.4685(3) 0.6861(2) 0.75155(11) 0.0400(4) Uani 1 1 d . . .
C2 C 0.4522(3) 0.8052(2) 0.69442(11) 0.0398(4) Uani 1 1 d . . .
H2 H 0.6042 0.8812 0.6970 0.048 Uiso 1 1 calc R . .
C3 C 0.3688(4) 0.7012(3) 0.60882(12) 0.0515(5) Uani 1 1 d . . .
C4 C 0.2355(5) 0.9579(4) 0.87957(14) 0.0737(7) Uani 1 1 d . . .
H4A H 0.0784 0.9535 0.8665 0.111 Uiso 1 1 calc R . .
H4B H 0.3021 1.0391 0.9291 0.111 Uiso 1 1 calc R . .
H4C H 0.2472 0.8473 0.8853 0.111 Uiso 1 1 calc R . .
C5 C 0.2179(6) 1.1876(5) 0.6605(3) 0.1207(16) Uani 1 1 d . . .
H5A H 0.0731 1.1131 0.6332 0.181 Uiso 1 1 calc R . .
H5B H 0.2899 1.2511 0.6243 0.181 Uiso 1 1 calc R . .
H5C H 0.1964 1.2650 0.7057 0.181 Uiso 1 1 calc R . .
C6 C 0.2950(8) 0.7176(5) 0.47323(17) 0.1065(12) Uani 1 1 d . . .
H6A H 0.3818 0.6398 0.4577 0.160 Uiso 1 1 calc R . .
H6B H 0.3145 0.8018 0.4409 0.160 Uiso 1 1 calc R . .
H6C H 0.1372 0.6561 0.4656 0.160 Uiso 1 1 calc R . .
C7 C 0.7195(3) 0.5516(2) 0.81587(11) 0.0404(4) Uani 1 1 d . . .
C8 C 0.7800(3) 0.4068(3) 0.78496(11) 0.0448(4) Uani 1 1 d . . .
C9 C 0.8164(3) 0.2950(3) 0.83165(14) 0.0530(5) Uani 1 1 d . . .
C10 C 0.7918(3) 0.3256(3) 0.91081(14) 0.0551(5) Uani 1 1 d . . .
C11 C 0.7374(3) 0.4708(3) 0.94370(12) 0.0520(5) Uani 1 1 d . . .
C12 C 0.7030(3) 0.5826(2) 0.89641(11) 0.0453(4) Uani 1 1 d . . .
F1 F 0.8008(2) 0.37338(17) 0.70780(7) 0.0617(3) Uani 1 1 d . . .
F2 F 0.8720(3) 0.15449(18) 0.80013(10) 0.0786(4) Uani 1 1 d . . .
F3 F 0.8260(3) 0.2168(2) 0.95650(10) 0.0827(5) Uani 1 1 d . . .
F4 F 0.7246(2) 0.5049(2) 1.02200(7) 0.0723(4) Uani 1 1 d . . .
F5 F 0.6574(2) 0.72615(17) 0.92997(8) 0.0635(4) Uani 1 1 d . . .
N1 N 0.6767(3) 0.6623(2) 0.76640(10) 0.0442(4) Uani 1 1 d . . .
H1N H 0.774(4) 0.708(3) 0.7445(14) 0.053(6) Uiso 1 1 d . . .
O1 O 0.3075(2) 0.61921(19) 0.78045(9) 0.0542(4) Uani 1 1 d . . .
O2 O 0.3111(4) 0.5509(2) 0.59102(11) 0.0843(6) Uani 1 1 d . . .
O3 O 0.0230(2) 0.84677(18) 0.70161(8) 0.0491(3) Uani 1 1 d . . .
O4 O 0.3537(3) 1.0085(2) 0.81638(9) 0.0603(4) Uani 1 1 d . . .
O5 O 0.3546(3) 1.09122(18) 0.68704(11) 0.0592(4) Uani 1 1 d . . .
O6 O 0.3736(4) 0.8017(2) 0.55780(10) 0.0777(5) Uani 1 1 d . . .
P1 P 0.26618(8) 0.93425(6) 0.72476(3) 0.04082(17) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 123.74(17) . . ?
O1 C1 C2 122.38(16) . . ?
N1 C1 C2 113.89(15) . . ?
C3 C2 C1 109.61(15) . . ?
C3 C2 P1 111.50(13) . . ?
C1 C2 P1 110.11(12) . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
P1 C2 H2 108.5 . . ?
O2 C3 O6 124.8(2) . . ?
O2 C3 C2 124.54(19) . . ?
O6 C3 C2 110.63(18) . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O5 C5 H5A 109.5 . . ?
O5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O6 C6 H6A 109.5 . . ?
O6 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O6 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 117.48(17) . . ?
C12 C7 N1 121.84(17) . . ?
C8 C7 N1 120.68(17) . . ?
F1 C8 C9 118.98(18) . . ?
F1 C8 C7 119.43(17) . . ?
C9 C8 C7 121.58(18) . . ?
F2 C9 C10 119.7(2) . . ?
F2 C9 C8 120.5(2) . . ?
C10 C9 C8 119.81(19) . . ?
F3 C10 C9 120.1(2) . . ?
F3 C10 C11 120.0(2) . . ?
C9 C10 C11 119.88(18) . . ?
F4 C11 C10 119.84(19) . . ?
F4 C11 C12 120.4(2) . . ?
C10 C11 C12 119.72(19) . . ?
F5 C12 C11 118.98(18) . . ?
F5 C12 C7 119.55(17) . . ?
C11 C12 C7 121.46(18) . . ?
C1 N1 C7 121.29(15) . . ?
C1 N1 H1N 118.8(17) . . ?
C7 N1 H1N 119.8(17) . . ?
C4 O4 P1 124.97(16) . . ?
C5 O5 P1 123.76(17) . . ?
C3 O6 C6 116.2(2) . . ?
O3 P1 O5 115.63(8) . . ?
O3 P1 O4 116.16(8) . . ?
O5 P1 O4 102.72(9) . . ?
O3 P1 C2 114.76(8) . . ?
O5 P1 C2 101.16(8) . . ?
O4 P1 C2 104.49(9) . . ?
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
C1 O1 1.213(2) . ?
C1 N1 1.352(2) . ?
C1 C2 1.524(2) . ?
C2 C3 1.524(3) . ?
C2 P1 1.8162(18) . ?
C2 H2 0.9800 . ?
C3 O2 1.180(3) . ?
C3 O6 1.311(3) . ?
C4 O4 1.440(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 O5 1.395(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O6 1.462(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.381(3) . ?
C7 C8 1.383(3) . ?
C7 N1 1.408(2) . ?
C8 F1 1.332(2) . ?
C8 C9 1.373(3) . ?
C9 F2 1.338(2) . ?
C9 C10 1.371(3) . ?
C10 F3 1.337(2) . ?
C10 C11 1.375(3) . ?
C11 F4 1.340(2) . ?
C11 C12 1.376(3) . ?
C12 F5 1.340(2) . ?
N1 H1N 0.79(2) . ?
O3 P1 1.4654(14) . ?
O4 P1 1.5619(16) . ?
O5 P1 1.5604(14) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O3 0.79(2) 1.97(2) 2.764(2) 172(2) 1_655
