#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/13/4101337.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_4101337
loop_
_publ_author_name
'Thu, Hung-Yat'
'Yu, Wing-Yiu'
'Che, Chi-Ming'
_publ_section_title
;
 Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via
 palladium-catalyzed cascade C-H activation/nitrene insertion.
;
_journal_issue                   28
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9048
_journal_page_last               9049
_journal_paper_doi               10.1021/ja062856v
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C14 H11 F3 N2 O'
_chemical_formula_sum            'C14 H11 F3 N2 O'
_chemical_formula_weight         280.25
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.356(2)
_cell_length_b                   17.055(3)
_cell_length_c                   7.4010(15)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1300.8(5)
_computing_cell_refinement       scalepack
_computing_data_collection       marcontrol
_computing_data_reduction        denzo
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.710
_diffrn_measured_fraction_theta_max 0.710
_diffrn_measurement_device_type  'marresearch IPDS mar300'
_diffrn_measurement_method       oscillation
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5855
_diffrn_reflns_theta_full        25.45
_diffrn_reflns_theta_max         25.45
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0589
_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)+(0.1237P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.1868
_reflns_number_gt                1094
_reflns_number_total             1710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja062856vsi20060501_054015.cif
_cod_data_source_block           mar1636a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4101337
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 0.8754(2) 0.59103(16) 0.1383(5) 0.1316(11) Uani 1 1 d .
F2 F 0.8125(3) 0.70574(16) 0.1241(6) 0.1619(16) Uani 1 1 d .
F3 F 0.8662(3) 0.6549(2) 0.3740(4) 0.1647(15) Uani 1 1 d .
O1 O 0.5872(2) 0.66856(13) 0.2518(4) 0.0845(9) Uani 1 1 d .
N1 N 0.6479(3) 0.54015(14) 0.2186(4) 0.0559(8) Uani 1 1 d .
N2 N 0.7708(3) 0.40598(15) 0.1863(4) 0.0699(9) Uani 1 1 d .
C1 C 0.6649(3) 0.61773(18) 0.2304(5) 0.0619(9) Uani 1 1 d .
C2 C 0.8032(4) 0.6427(2) 0.2162(7) 0.0812(11) Uani 1 1 d .
C3 C 0.5333(3) 0.49646(17) 0.2354(4) 0.0516(8) Uani 1 1 d .
C4 C 0.4193(3) 0.53235(18) 0.2728(4) 0.0577(9) Uani 1 1 d .
H4 H 0.4174 0.5866 0.2850 0.069 Uiso 1 1 calc R
C5 C 0.3074(3) 0.48954(19) 0.2925(5) 0.0630(9) Uani 1 1 d .
C6 C 0.3154(3) 0.4084(2) 0.2806(5) 0.0679(10) Uani 1 1 d .
H6 H 0.2432 0.3781 0.2991 0.082 Uiso 1 1 calc R
C7 C 0.4270(3) 0.3725(2) 0.2424(5) 0.0683(10) Uani 1 1 d .
H7 H 0.4283 0.3181 0.2350 0.082 Uiso 1 1 calc R
C8 C 0.5403(3) 0.41423(16) 0.2139(4) 0.0520(8) Uani 1 1 d .
C9 C 0.6546(3) 0.37045(17) 0.1628(4) 0.0578(9) Uani 1 1 d .
C10 C 0.6450(4) 0.29562(18) 0.0891(5) 0.0699(10) Uani 1 1 d .
H10 H 0.5644 0.2715 0.0676 0.084 Uiso 1 1 calc R
C11 C 0.7547(5) 0.2574(2) 0.0482(5) 0.0829(12) Uani 1 1 d .
H11 H 0.7485 0.2069 0.0006 0.099 Uiso 1 1 calc R
C12 C 0.8723(5) 0.2927(2) 0.0765(6) 0.0888(12) Uani 1 1 d .
H12 H 0.9477 0.2671 0.0510 0.107 Uiso 1 1 calc R
C13 C 0.8754(4) 0.3672(2) 0.1440(6) 0.0878(12) Uani 1 1 d .
H13 H 0.9553 0.3923 0.1616 0.105 Uiso 1 1 calc R
C14 C 0.1840(4) 0.5298(2) 0.3276(6) 0.0849(12) Uani 1 1 d .
H14A H 0.1113 0.4983 0.2813 0.127 Uiso 1 1 calc R
H14B H 0.1794 0.5799 0.2681 0.127 Uiso 1 1 calc R
H14C H 0.1820 0.5371 0.4559 0.127 Uiso 1 1 calc R
H1 H 0.714(3) 0.5130(19) 0.200(4) 0.066(10) 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
F F 0.0171 0.0103 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C3 128.4(3)
C13 N2 C9 118.9(3)
O1 C1 N1 129.5(3)
O1 C1 C2 117.2(3)
N1 C1 C2 113.3(3)
F2 C2 F3 106.7(3)
F2 C2 F1 104.5(4)
F3 C2 F1 104.1(4)
F2 C2 C1 113.4(4)
F3 C2 C1 112.3(4)
F1 C2 C1 115.0(3)
C4 C3 C8 121.0(3)
C4 C3 N1 121.6(3)
C8 C3 N1 117.4(3)
C3 C4 C5 121.8(3)
C4 C5 C6 117.5(3)
C4 C5 C14 120.8(3)
C6 C5 C14 121.7(3)
C7 C6 C5 121.2(3)
C6 C7 C8 122.8(3)
C7 C8 C3 115.6(3)
C7 C8 C9 118.9(3)
C3 C8 C9 125.4(3)
N2 C9 C10 119.7(3)
N2 C9 C8 117.9(3)
C10 C9 C8 122.4(3)
C11 C10 C9 119.7(4)
C12 C11 C10 120.5(4)
C11 C12 C13 117.3(4)
N2 C13 C12 123.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.324(5)
F2 C2 1.281(4)
F3 C2 1.297(5)
O1 C1 1.204(4)
N1 C1 1.337(4)
N1 C3 1.416(4)
N2 C13 1.333(4)
N2 C9 1.343(4)
C1 C2 1.508(5)
C3 C4 1.382(4)
C3 C8 1.414(4)
C4 C5 1.389(4)
C5 C6 1.390(5)
C5 C14 1.496(4)
C6 C7 1.362(5)
C7 C8 1.406(4)
C8 C9 1.480(4)
C9 C10 1.388(4)
C10 C11 1.369(5)
C11 C12 1.356(5)
C12 C13 1.364(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660017
