#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:07:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178769 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/23/4102381.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_4102381
loop_
_publ_author_name
'Hidenori Kinoshita'
'Oscar J. Ingham'
'Winnie W. Ong'
'Aaron B. Beeler'
'John A. Porco'
_publ_section_title
;
 Tandem Processes Identified from Reaction Screening: Nucleophilic
 Addition to Aryl N-Phosphinylimines Employing La(III)-TFAA Activation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6412
_journal_page_last               6418
_journal_paper_doi               10.1021/ja100346w
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C21 H20 F3 N O4'
_chemical_formula_sum            'C21 H20 F3 N O4'
_chemical_formula_weight         407.38
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.879(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9153(12)
_cell_length_b                   7.2960(9)
_cell_length_c                   23.168(3)
_cell_measurement_reflns_used    5543
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.64
_cell_measurement_theta_min      2.48
_cell_volume                     1840.8(4)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16253
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_correction_T_min  0.9199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0433
_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)+(0.0427P)²+0.7230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3652
_reflns_number_total             4577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja100346w_si_003.cif
_cod_data_source_block           compound_49
_cod_original_cell_volume        1840.9(4)
_cod_database_code               4102381
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
F1 F 0.82397(7) 0.31822(11) 0.28243(3) 0.03083(19) Uani 1 1 d .
F2 F 0.78282(6) 0.46218(11) 0.20268(3) 0.02613(17) Uani 1 1 d .
F3 F 0.74048(7) 0.17668(12) 0.20911(4) 0.0413(2) Uani 1 1 d .
O1 O 0.99965(8) 0.11923(13) 0.23267(4) 0.0272(2) Uani 1 1 d .
O2 O 1.33539(7) 0.38963(13) -0.02390(3) 0.0236(2) Uani 1 1 d .
O3 O 1.13166(8) 0.33591(12) -0.10683(3) 0.02036(19) Uani 1 1 d .
O4 O 0.91695(7) 0.23520(13) -0.07206(3) 0.0223(2) Uani 1 1 d .
N1 N 0.98624(8) 0.32834(14) 0.15946(4) 0.0168(2) Uani 1 1 d .
H1N H 0.9515(13) 0.423(2) 0.1473(6) 0.027(4) Uiso 1 1 d .
C1 C 1.09791(10) 0.26952(17) 0.13349(4) 0.0157(2) Uani 1 1 d .
H1 H 1.1089(10) 0.1434(18) 0.1435(5) 0.011(3) Uiso 1 1 d .
C2 C 1.21417(10) 0.38074(17) 0.15259(5) 0.0179(2) Uani 1 1 d .
H2 H 1.1897(12) 0.506(2) 0.1588(6) 0.022(3) Uiso 1 1 d .
C3 C 1.29153(11) 0.29464(19) 0.20322(5) 0.0225(3) Uani 1 1 d .
H3B H 1.2442(12) 0.233(2) 0.2308(6) 0.023(3) Uiso 1 1 d .
H3A H 1.3418(13) 0.390(2) 0.2241(6) 0.029(4) Uiso 1 1 d .
C4 C 1.37317(10) 0.16186(18) 0.17370(5) 0.0201(3) Uani 1 1 d .
C5 C 1.43786(11) 0.0129(2) 0.19632(5) 0.0261(3) Uani 1 1 d .
H5 H 1.4367(13) -0.016(2) 0.2369(6) 0.033(4) Uiso 1 1 d .
C6 C 1.50629(11) -0.0923(2) 0.16048(6) 0.0283(3) Uani 1 1 d .
H6 H 1.5519(14) -0.198(2) 0.1750(6) 0.037(4) Uiso 1 1 d .
C7 C 1.51063(11) -0.0481(2) 0.10247(5) 0.0262(3) Uani 1 1 d .
H7 H 1.5559(13) -0.122(2) 0.0776(6) 0.030(4) Uiso 1 1 d .
C8 C 1.44603(10) 0.10089(18) 0.07950(5) 0.0207(3) Uani 1 1 d .
H8 H 1.4481(11) 0.1338(18) 0.0389(5) 0.016(3) Uiso 1 1 d .
C9 C 1.37670(10) 0.20566(17) 0.11526(5) 0.0178(2) Uani 1 1 d .
C10 C 1.29460(10) 0.36767(17) 0.09976(5) 0.0168(2) Uani 1 1 d .
H10 H 1.3450(11) 0.4775(19) 0.0952(5) 0.020(3) Uiso 1 1 d .
C11 C 1.20191(10) 0.33610(16) 0.04977(4) 0.0152(2) Uani 1 1 d .
C12 C 1.21888(10) 0.34946(16) -0.00894(5) 0.0161(2) Uani 1 1 d .
C13 C 1.12008(10) 0.31408(16) -0.04836(4) 0.0160(2) Uani 1 1 d .
C14 C 1.00565(10) 0.26380(16) -0.02886(5) 0.0163(2) Uani 1 1 d .
C15 C 0.99004(10) 0.24598(17) 0.02983(5) 0.0167(2) Uani 1 1 d .
H15 H 0.9127(11) 0.2091(18) 0.0435(5) 0.016(3) Uiso 1 1 d .
C16 C 1.08942(10) 0.28396(16) 0.06826(4) 0.0150(2) Uani 1 1 d .
C17 C 0.94913(10) 0.24477(17) 0.20644(5) 0.0186(3) Uani 1 1 d .
C18 C 0.82337(11) 0.30436(18) 0.22546(5) 0.0210(3) Uani 1 1 d .
C19 C 1.35279(12) 0.5221(2) -0.06731(6) 0.0327(3) Uani 1 1 d .
H19A H 1.3471 0.4628 -0.1053 0.049 Uiso 1 1 calc R
H19B H 1.4340 0.5784 -0.0604 0.049 Uiso 1 1 calc R
H19C H 1.2893 0.6169 -0.0662 0.049 Uiso 1 1 calc R
C20 C 1.13703(13) 0.16702(19) -0.13827(5) 0.0264(3) Uani 1 1 d .
H20C H 1.1372(14) 0.193(2) -0.1784(7) 0.043(4) Uiso 1 1 d .
H20B H 1.0677(15) 0.087(3) -0.1303(7) 0.049(5) Uiso 1 1 d .
H20A H 1.2107(18) 0.097(3) -0.1253(8) 0.064(6) Uiso 1 1 d .
C21 C 0.80036(11) 0.17379(19) -0.05617(5) 0.0237(3) Uani 1 1 d .
H21C H 0.7609(12) 0.269(2) -0.0317(6) 0.026(4) Uiso 1 1 d .
H21B H 0.8074(12) 0.054(2) -0.0331(6) 0.025(4) Uiso 1 1 d .
H21A H 0.7532(13) 0.155(2) -0.0922(6) 0.032(4) 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 O2 C19 119.74(9)
C13 O3 C20 114.16(9)
C14 O4 C21 117.58(9)
C17 N1 C1 120.66(10)
N1 C1 C16 113.28(9)
N1 C1 C2 114.83(9)
C16 C1 C2 104.08(9)
C3 C2 C1 113.77(10)
C3 C2 C10 105.42(9)
C1 C2 C10 103.80(9)
C4 C3 C2 103.16(9)
C5 C4 C9 120.15(11)
C5 C4 C3 129.45(11)
C9 C4 C3 110.39(10)
C4 C5 C6 119.42(11)
C5 C6 C7 120.50(13)
C8 C7 C6 120.40(12)
C7 C8 C9 119.18(11)
C8 C9 C4 120.34(11)
C8 C9 C10 128.82(10)
C4 C9 C10 110.80(10)
C11 C10 C9 114.86(10)
C11 C10 C2 103.25(9)
C9 C10 C2 102.58(9)
C16 C11 C12 120.23(10)
C16 C11 C10 111.68(9)
C12 C11 C10 128.07(10)
O2 C12 C11 116.73(9)
O2 C12 C13 124.40(10)
C11 C12 C13 118.81(10)
O3 C13 C12 120.39(10)
O3 C13 C14 119.26(9)
C12 C13 C14 120.29(10)
O4 C14 C15 125.29(10)
O4 C14 C13 114.03(9)
C15 C14 C13 120.68(10)
C16 C15 C14 117.94(10)
C11 C16 C15 122.02(10)
C11 C16 C1 109.49(9)
C15 C16 C1 128.43(10)
O1 C17 N1 127.00(11)
O1 C17 C18 117.16(10)
N1 C17 C18 115.60(10)
F1 C18 F2 107.98(10)
F1 C18 F3 107.08(10)
F2 C18 F3 106.89(10)
F1 C18 C17 111.37(9)
F2 C18 C17 114.33(10)
F3 C18 C17 108.87(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C18 1.3233(13)
F2 C18 1.3299(15)
F3 C18 1.3355(15)
O1 C17 1.2112(15)
O2 C12 1.3722(13)
O2 C19 1.4171(16)
O3 C13 1.3782(12)
O3 C20 1.4346(16)
O4 C14 1.3607(13)
O4 C21 1.4210(14)
N1 C17 1.3343(14)
N1 C1 1.4599(14)
C1 C16 1.5115(14)
C1 C2 1.5456(16)
C2 C3 1.5328(16)
C2 C10 1.5567(15)
C3 C4 1.5109(17)
C4 C5 1.3801(18)
C4 C9 1.3943(15)
C5 C6 1.3857(19)
C6 C7 1.3859(18)
C7 C8 1.3826(18)
C8 C9 1.3886(16)
C9 C10 1.5119(17)
C10 C11 1.5031(15)
C11 C16 1.3810(15)
C11 C12 1.3886(15)
C12 C13 1.3895(15)
C13 C14 1.4054(15)
C14 C15 1.3879(15)
C15 C16 1.3840(15)
C17 C18 1.5327(16)
