#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:07:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178769 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/23/4102383.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_4102383
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         'C28 H26 F3 N O4'
_chemical_formula_sum            'C28 H26 F3 N O4'
_chemical_formula_weight         497.50
_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                90.235(12)
_cell_angle_beta                 115.124(11)
_cell_angle_gamma                105.603(11)
_cell_formula_units_Z            2
_cell_length_a                   10.320(3)
_cell_length_b                   11.387(4)
_cell_length_c                   12.207(4)
_cell_measurement_reflns_used    3714
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.88
_cell_measurement_theta_min      2.45
_cell_volume                     1239.3(7)
_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 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18829
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         6124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          1.113
_refine_ls_shift/su_mean         0.030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                3683
_reflns_number_total             6124
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja100346w_si_005.cif
_cod_data_source_block           Compound_86
_cod_original_cell_volume        1239.4(7)
_cod_database_code               4102383
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
F1 F -0.41694(12) -0.09825(12) 0.41512(11) 0.0501(4) Uani 0.5696(10) 1 d P A 1
F2 F -0.29254(12) -0.08979(12) 0.31364(10) 0.0470(4) Uani 0.5696(10) 1 d P A 1
F3 F -0.36903(12) 0.06109(10) 0.33183(11) 0.0386(4) Uani 0.5696(10) 1 d P A 1
F1A F -0.4280(4) -0.0553(4) 0.4179(4) 0.0701(12) Uiso 0.2304(10) 1 d P A 2
F2A F -0.3024(3) -0.1207(3) 0.3423(3) 0.0504(9) Uiso 0.2304(10) 1 d P A 2
F3A F -0.3265(3) 0.0545(3) 0.3123(3) 0.0551(10) Uiso 0.2304(10) 1 d P A 2
F1B F -0.3840(6) -0.1258(5) 0.4110(6) 0.113(3) Uani 0.20 1 d P A 3
F2B F -0.2796(5) -0.0443(6) 0.2997(4) 0.091(2) Uani 0.20 1 d P A 3
F3B F -0.3991(4) 0.0518(4) 0.3598(4) 0.0633(14) Uani 0.20 1 d P A 3
O1 O -0.10699(8) -0.04391(6) 0.57054(7) 0.0454(2) Uani 1 1 d . . .
O2 O 0.24835(7) 0.46267(6) 0.42367(6) 0.03420(18) Uani 1 1 d . . .
O3 O 0.28121(6) 0.67515(6) 0.54598(6) 0.03440(19) Uani 1 1 d . . .
O4 O 0.17783(6) 0.67394(6) 0.71588(6) 0.03399(19) Uani 1 1 d . . .
N1 N -0.11934(8) 0.15001(7) 0.53562(7) 0.0287(2) Uani 1 1 d . . .
H1N H -0.1709(10) 0.1950(10) 0.4884(9) 0.044(3) Uiso 1 1 d . . .
C1 C 0.00943(10) 0.21443(9) 0.65066(9) 0.0281(2) Uani 1 1 d . . .
H1 H 0.0798(9) 0.1708(8) 0.6679(8) 0.027(3) Uiso 1 1 d . . .
C2 C 0.08077(9) 0.34261(8) 0.62972(8) 0.0252(2) Uani 1 1 d . . .
C3 C 0.13425(9) 0.34419(9) 0.54247(8) 0.0270(2) Uani 1 1 d . . .
H3 H 0.1228(9) 0.2708(9) 0.5006(8) 0.034(3) Uiso 1 1 d . . .
C4 C 0.20019(9) 0.45312(9) 0.51233(8) 0.0271(2) Uani 1 1 d . . .
C5 C 0.21889(9) 0.56363(8) 0.57459(8) 0.0270(2) Uani 1 1 d . . .
C6 C 0.16554(9) 0.56246(8) 0.66144(9) 0.0268(2) Uani 1 1 d . . .
C7 C 0.09429(9) 0.45230(8) 0.69030(8) 0.0256(2) Uani 1 1 d . . .
C8 C 0.04010(10) 0.45834(9) 0.78715(9) 0.0307(3) Uani 1 1 d . . .
H8B H 0.0624(9) 0.5474(9) 0.8129(8) 0.036(3) Uiso 1 1 d . . .
H8A H -0.0732(10) 0.4224(9) 0.7494(9) 0.041(3) Uiso 1 1 d . . .
C9 C 0.11485(9) 0.39282(9) 0.89309(8) 0.0285(2) Uani 1 1 d . . .
C10 C 0.07603(10) 0.26989(9) 0.87431(9) 0.0308(3) Uani 1 1 d . . .
C11 C -0.04218(10) 0.20309(9) 0.75115(9) 0.0330(3) Uani 1 1 d . . .
H11B H -0.1312(9) 0.2335(8) 0.7227(8) 0.029(3) Uiso 1 1 d . . .
H11A H -0.0762(10) 0.1160(9) 0.7566(9) 0.037(3) Uiso 1 1 d . . .
C12 C -0.16559(10) 0.02894(9) 0.50976(9) 0.0321(3) Uani 1 1 d . A .
C13 C -0.30999(11) -0.02327(9) 0.39271(10) 0.0372(3) Uani 1 1 d . . .
C14 C 0.21168(11) 0.35241(10) 0.34734(10) 0.0384(3) Uani 1 1 d . . .
H14C H 0.2617(10) 0.2931(9) 0.3949(9) 0.041(3) Uiso 1 1 d . . .
H14B H 0.2538(11) 0.3823(10) 0.2894(10) 0.052(3) Uiso 1 1 d . . .
H14A H 0.1016(11) 0.3117(10) 0.3067(9) 0.049(3) Uiso 1 1 d . . .
C15 C 0.43530(11) 0.69901(11) 0.56844(11) 0.0452(3) Uani 1 1 d . . .
H15C H 0.4497(13) 0.6465(12) 0.5108(12) 0.079(4) Uiso 1 1 d . . .
H15B H 0.4645(13) 0.7761(13) 0.5519(12) 0.077(4) Uiso 1 1 d . . .
H15A H 0.4906(14) 0.6910(13) 0.6482(13) 0.089(5) Uiso 1 1 d . . .
C16 C 0.31897(12) 0.72599(10) 0.82083(10) 0.0426(3) Uani 1 1 d . . .
H16C H 0.4017(11) 0.7432(10) 0.7961(9) 0.050(3) Uiso 1 1 d . . .
H16B H 0.3162(11) 0.8021(11) 0.8572(10) 0.057(4) Uiso 1 1 d . . .
H16A H 0.3378(11) 0.6658(11) 0.8878(10) 0.059(4) Uiso 1 1 d . . .
C17 C 0.23292(10) 0.47052(9) 1.00851(9) 0.0292(2) Uani 1 1 d . . .
C18 C 0.37341(10) 0.45273(9) 1.06736(9) 0.0343(3) Uani 1 1 d . . .
H18 H 0.3922(10) 0.3902(10) 1.0298(9) 0.044(3) Uiso 1 1 d . . .
C19 C 0.48359(11) 0.52753(10) 1.17303(10) 0.0416(3) Uani 1 1 d . . .
H19 H 0.5840(12) 0.5209(11) 1.2132(10) 0.064(4) Uiso 1 1 d . . .
C20 C 0.45602(11) 0.62092(11) 1.22310(10) 0.0440(3) Uani 1 1 d . . .
H20 H 0.5332(10) 0.6737(10) 1.3015(10) 0.051(3) Uiso 1 1 d . . .
C21 C 0.31858(11) 0.64116(10) 1.16544(10) 0.0434(3) Uani 1 1 d . . .
H21 H 0.3018(12) 0.7122(11) 1.1974(10) 0.056(3) Uiso 1 1 d . . .
C22 C 0.20846(10) 0.56770(10) 1.05881(9) 0.0361(3) Uani 1 1 d . . .
H22 H 0.1145(9) 0.5847(9) 1.0199(8) 0.031(3) Uiso 1 1 d . . .
C23 C 0.14208(10) 0.19199(9) 0.96752(9) 0.0330(3) Uani 1 1 d . . .
C24 C 0.11788(12) 0.18309(10) 1.07040(9) 0.0392(3) Uani 1 1 d . . .
H24 H 0.0547(11) 0.2255(10) 1.0784(9) 0.045(3) Uiso 1 1 d . . .
C25 C 0.17769(13) 0.10929(10) 1.15569(10) 0.0459(3) Uani 1 1 d . . .
H25 H 0.1524(12) 0.0986(11) 1.2214(10) 0.060(4) Uiso 1 1 d . . .
C26 C 0.26206(13) 0.04311(11) 1.13907(11) 0.0474(4) Uani 1 1 d . . .
H26 H 0.3020(11) -0.0080(11) 1.1976(10) 0.059(4) Uiso 1 1 d . . .
C27 C 0.28641(13) 0.04958(11) 1.03621(12) 0.0522(4) Uani 1 1 d . . .
H27 H 0.3469(12) 0.0031(11) 1.0234(10) 0.062(4) Uiso 1 1 d . . .
C28 C 0.22625(12) 0.12300(11) 0.95129(10) 0.0469(3) Uani 1 1 d . . .
H28 H 0.2447(12) 0.1280(11) 0.8847(10) 0.062(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
C4 O2 C14 117.00(8)
C5 O3 C15 115.06(8)
C6 O4 C16 113.28(8)
C12 N1 C1 122.09(8)
N1 C1 C2 108.78(8)
N1 C1 C11 108.04(8)
C2 C1 C11 118.49(8)
C3 C2 C7 120.38(9)
C3 C2 C1 114.66(9)
C7 C2 C1 124.96(10)
C4 C3 C2 121.52(9)
O2 C4 C3 125.15(9)
O2 C4 C5 115.96(9)
C3 C4 C5 118.89(10)
O3 C5 C6 119.03(9)
O3 C5 C4 121.12(10)
C6 C5 C4 119.71(9)
O4 C6 C5 118.06(8)
O4 C6 C7 120.01(10)
C5 C6 C7 121.87(9)
C2 C7 C6 117.55(10)
C2 C7 C8 123.58(9)
C6 C7 C8 118.85(9)
C9 C8 C7 111.54(9)
C10 C9 C17 124.61(9)
C10 C9 C8 117.97(8)
C17 C9 C8 117.32(9)
C9 C10 C23 124.67(8)
C9 C10 C11 118.92(9)
C23 C10 C11 116.41(9)
C10 C11 C1 114.46(8)
O1 C12 N1 127.03(8)
O1 C12 C13 117.82(9)
N1 C12 C13 115.14(9)
F3 C13 F2 105.83(12)
F3 C13 F1 105.89(11)
F2 C13 F1 105.64(11)
F3 C13 C12 114.70(9)
F2 C13 C12 112.67(10)
F1 C13 C12 111.44(10)
C18 C17 C22 117.61(8)
C18 C17 C9 121.56(9)
C22 C17 C9 120.77(9)
C19 C18 C17 121.04(11)
C20 C19 C18 120.50(10)
C21 C20 C19 119.38(9)
C20 C21 C22 120.42(11)
C21 C22 C17 121.01(10)
C24 C23 C28 117.90(11)
C24 C23 C10 121.36(10)
C28 C23 C10 120.71(10)
C25 C24 C23 121.09(12)
C26 C25 C24 120.25(12)
C25 C26 C27 119.67(12)
C28 C27 C26 119.88(13)
C27 C28 C23 121.20(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C13 1.3317(17)
F2 C13 1.3240(19)
F3 C13 1.3350(16)
F1A C13 1.338(5)
F2A C13 1.302(4)
F3A C13 1.312(4)
F1B C13 1.290(6)
F2B C13 1.336(6)
F3B C13 1.360(5)
O1 C12 1.2240(13)
O2 C4 1.3634(13)
O2 C14 1.4224(13)
O3 C5 1.3796(12)
O3 C15 1.4404(13)
O4 C6 1.3799(12)
O4 C16 1.4349(12)
N1 C12 1.3201(13)
N1 C1 1.4692(11)
C1 C2 1.5240(14)
C1 C11 1.5246(16)
C2 C3 1.3904(15)
C2 C7 1.3920(14)
C3 C4 1.3781(14)
C4 C5 1.3911(14)
C5 C6 1.3854(15)
C6 C7 1.4020(14)
C7 C8 1.5155(15)
C8 C9 1.5148(14)
C9 C10 1.3380(15)
C9 C17 1.4848(13)
C10 C23 1.4903(15)
C10 C11 1.5036(13)
C12 C13 1.5246(13)
C17 C18 1.3907(14)
C17 C22 1.3934(16)
C18 C19 1.3809(14)
C19 C20 1.3749(18)
C20 C21 1.3748(16)
C21 C22 1.3817(14)
C23 C24 1.3797(16)
C23 C28 1.3867(17)
C24 C25 1.3826(16)
C25 C26 1.3671(19)
C26 C27 1.380(2)
C27 C28 1.3779(17)
