#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:13:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178840 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/94/4109471.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_4109471
loop_
_publ_author_name
'Zhenjie Lu'
'Yu Zhang'
'William D. Wulff'
_publ_section_title
;
 Direct Access to N-H-Aziridines from Asymmetric Catalytic Aziridination
 with Borate Catalysts Derived from Vaulted Binaphthol and Vaulted
 Biphenanthrol Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7185
_journal_page_last               7194
_journal_paper_doi               10.1021/ja069371r
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C26 H26 F3 N O5'
_chemical_formula_weight         489.48
_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                113.04(3)
_cell_angle_beta                 100.21(3)
_cell_angle_gamma                101.66(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6523(19)
_cell_length_b                   11.259(2)
_cell_length_c                   12.919(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1213.1(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.1196
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10037
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.107
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.805
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.1725
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.2037
_reflns_number_gt                2331
_reflns_number_total             5537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja069371rrom20061231_091630.cif
_cod_data_source_block           wf041305
_cod_original_cell_volume        1213.0(4)
_cod_database_code               4109471
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
C1 C 0.5502(3) 0.2689(3) -0.0953(3) 0.0315(7) Uani 1 1 d .
H1A H 0.4860 0.2713 -0.1619 0.038 Uiso 1 1 calc R
N2 N 0.4688(3) 0.2767(3) -0.0053(2) 0.0294(6) Uani 1 1 d .
H2A H 0.424(3) 0.353(3) 0.008(2) 0.034(8) Uiso 1 1 d .
H2B H 0.534(3) 0.298(3) 0.059(3) 0.029(9) Uiso 1 1 d .
C3 C 0.3471(3) 0.1482(3) -0.0308(3) 0.0326(8) Uani 1 1 d .
H3A H 0.3963 0.0906 -0.0077 0.039 Uiso 1 1 calc R
C4 C 0.2703(3) 0.0693(3) -0.1611(3) 0.0338(8) Uani 1 1 d .
C5 C 0.2642(4) -0.0654(3) -0.2173(3) 0.0418(9) Uani 1 1 d .
H5A H 0.3033 -0.1067 -0.1744 0.050 Uiso 1 1 calc R
C6 C 0.1996(4) -0.1396(4) -0.3383(3) 0.0551(10) Uani 1 1 d .
H6A H 0.1951 -0.2302 -0.3760 0.066 Uiso 1 1 calc R
C7 C 0.1427(4) -0.0776(4) -0.4008(3) 0.0604(11) Uani 1 1 d .
H7A H 0.1008 -0.1265 -0.4815 0.073 Uiso 1 1 calc R
C8 C 0.1467(4) 0.0564(4) -0.3459(3) 0.0567(11) Uani 1 1 d .
H8A H 0.1075 0.0975 -0.3890 0.068 Uiso 1 1 calc R
C9 C 0.2099(4) 0.1287(3) -0.2255(3) 0.0420(9) Uani 1 1 d .
H9A H 0.2116 0.2185 -0.1878 0.050 Uiso 1 1 calc R
C10 C 0.2489(4) 0.1880(3) 0.0479(3) 0.0356(8) Uani 1 1 d .
C11 C 0.0997(4) 0.1687(4) 0.0061(3) 0.0504(10) Uani 1 1 d .
H11A H 0.0564 0.1327 -0.0742 0.061 Uiso 1 1 calc R
C12 C 0.0142(4) 0.2022(4) 0.0821(4) 0.0586(11) Uani 1 1 d .
H12A H -0.0860 0.1878 0.0525 0.070 Uiso 1 1 calc R
C13 C 0.0765(5) 0.2567(4) 0.2011(4) 0.0643(12) Uani 1 1 d .
H13A H 0.0192 0.2807 0.2522 0.077 Uiso 1 1 calc R
C14 C 0.2253(5) 0.2756(4) 0.2445(4) 0.0674(12) Uani 1 1 d .
H14A H 0.2684 0.3114 0.3248 0.081 Uiso 1 1 calc R
C15 C 0.3086(4) 0.2410(4) 0.1678(3) 0.0517(10) Uani 1 1 d .
H15A H 0.4083 0.2536 0.1976 0.062 Uiso 1 1 calc R
C16 C 0.6927(3) 0.3902(3) -0.0439(3) 0.0327(8) Uani 1 1 d .
H16A H 0.7629 0.3805 0.0149 0.039 Uiso 1 1 calc R
O17 O 0.6606(2) 0.5143(2) 0.0113(2) 0.0338(5) Uani 1 1 d .
H17 H 0.664(4) 0.528(3) 0.086(3) 0.057(11) Uiso 1 1 d .
C18 C 0.7606(3) 0.3884(3) -0.1408(3) 0.0319(8) Uani 1 1 d .
C19 C 0.8979(4) 0.3698(3) -0.1393(3) 0.0399(8) Uani 1 1 d .
H19A H 0.9510 0.3606 -0.0769 0.048 Uiso 1 1 calc R
C20 C 0.9568(4) 0.3650(3) -0.2307(3) 0.0486(10) Uani 1 1 d .
H20A H 1.0497 0.3532 -0.2290 0.058 Uiso 1 1 calc R
C21 C 0.8790(4) 0.3774(3) -0.3235(3) 0.0496(10) Uani 1 1 d .
H21A H 0.9189 0.3736 -0.3848 0.060 Uiso 1 1 calc R
C22 C 0.7436(4) 0.3953(4) -0.3261(3) 0.0529(10) Uani 1 1 d .
H22A H 0.6908 0.4029 -0.3896 0.063 Uiso 1 1 calc R
C23 C 0.6837(4) 0.4023(4) -0.2347(3) 0.0462(9) Uani 1 1 d .
H23A H 0.5917 0.4163 -0.2364 0.055 Uiso 1 1 calc R
C24 C 0.5905(4) 0.1385(3) -0.1387(3) 0.0380(8) Uani 1 1 d .
O25 O 0.6318(3) 0.0908(2) -0.0747(2) 0.0480(6) Uani 1 1 d .
O26 O 0.5790(3) 0.0911(2) -0.2519(2) 0.0547(7) Uani 1 1 d .
C27 C 0.6288(6) -0.0277(4) -0.3025(4) 0.0879(16) Uani 1 1 d .
H27A H 0.7131 -0.0219 -0.2452 0.106 Uiso 1 1 calc R
H27B H 0.5505 -0.1084 -0.3212 0.106 Uiso 1 1 calc R
C28 C 0.6666(14) -0.0376(8) -0.4006(9) 0.266(7) Uani 1 1 d .
H28A H 0.6974 -0.1171 -0.4323 0.398 Uiso 1 1 calc R
H28B H 0.7462 0.0409 -0.3817 0.398 Uiso 1 1 calc R
H28C H 0.5832 -0.0436 -0.4574 0.398 Uiso 1 1 calc R
C30 C 0.6878(3) 0.4828(4) 0.2677(3) 0.0364(8) Uani 1 1 d .
O31 O 0.6714(3) 0.3602(2) 0.2100(2) 0.0470(6) Uani 1 1 d .
O32 O 0.6747(2) 0.5683(2) 0.23202(19) 0.0435(6) Uani 1 1 d .
C33 C 0.7287(5) 0.5350(4) 0.4004(3) 0.0560(11) Uani 1 1 d .
F34 F 0.6191(3) 0.5107(5) 0.4357(2) 0.203(3) Uani 1 1 d .
F35 F 0.8007(4) 0.6646(3) 0.4593(2) 0.1219(12) Uani 1 1 d .
F36 F 0.8268(4) 0.4873(3) 0.4413(2) 0.1185(12) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 C24 110.6(2)
N2 C1 C16 110.9(2)
C24 C1 C16 109.2(2)
C1 N2 C3 117.5(2)
C10 C3 C4 116.1(3)
C10 C3 N2 108.7(2)
C4 C3 N2 110.6(2)
C9 C4 C5 119.3(3)
C9 C4 C3 121.9(3)
C5 C4 C3 118.8(3)
C4 C5 C6 120.3(3)
C7 C6 C5 119.3(4)
C6 C7 C8 121.0(4)
C7 C8 C9 119.1(4)
C4 C9 C8 120.9(3)
C15 C10 C11 117.6(3)
C15 C10 C3 118.8(3)
C11 C10 C3 123.5(3)
C12 C11 C10 121.0(4)
C13 C12 C11 120.3(4)
C12 C13 C14 119.5(4)
C15 C14 C13 119.5(4)
C14 C15 C10 122.1(4)
O17 C16 C18 111.0(2)
O17 C16 C1 110.4(2)
C18 C16 C1 109.2(2)
C19 C18 C23 118.9(3)
C19 C18 C16 121.0(3)
C23 C18 C16 120.1(3)
C18 C19 C20 120.1(3)
C21 C20 C19 120.4(3)
C22 C21 C20 120.0(3)
C21 C22 C23 120.5(3)
C18 C23 C22 120.1(3)
O25 C24 O26 126.7(3)
O25 C24 C1 122.6(3)
O26 C24 C1 110.6(3)
C24 O26 C27 116.1(3)
C28 C27 O26 111.4(5)
O32 C30 O31 128.9(3)
O32 C30 C33 115.3(3)
O31 C30 C33 115.8(3)
F34 C33 F36 107.9(4)
F34 C33 F35 108.9(4)
F36 C33 F35 98.8(4)
F34 C33 C30 112.3(3)
F36 C33 C30 113.9(3)
F35 C33 C30 114.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.499(4)
C1 C24 1.511(4)
C1 C16 1.551(4)
N2 C3 1.544(4)
C3 C10 1.514(4)
C3 C4 1.514(4)
C4 C9 1.379(4)
C4 C5 1.386(4)
C5 C6 1.396(5)
C6 C7 1.372(5)
C7 C8 1.382(5)
C8 C9 1.387(5)
C10 C15 1.382(5)
C10 C11 1.385(5)
C11 C12 1.382(5)
C12 C13 1.374(6)
C13 C14 1.385(6)
C14 C15 1.373(5)
C16 O17 1.425(3)
C16 C18 1.508(4)
C18 C19 1.382(4)
C18 C23 1.387(4)
C19 C20 1.385(5)
C20 C21 1.370(5)
C21 C22 1.359(5)
C22 C23 1.387(5)
C24 O25 1.203(4)
C24 O26 1.321(4)
O26 C27 1.460(4)
C27 C28 1.349(8)
C30 O32 1.238(4)
C30 O31 1.245(4)
C30 C33 1.523(5)
C33 F34 1.246(5)
C33 F36 1.309(5)
C33 F35 1.313(5)
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
C24 C1 N2 C3 -44.0(4)
C16 C1 N2 C3 -165.2(3)
C1 N2 C3 C10 -162.3(3)
C1 N2 C3 C4 -33.7(4)
C10 C3 C4 C9 71.0(4)
N2 C3 C4 C9 -53.5(4)
C10 C3 C4 C5 -110.8(3)
N2 C3 C4 C5 124.8(3)
C9 C4 C5 C6 1.0(5)
C3 C4 C5 C6 -177.4(3)
C4 C5 C6 C7 0.2(5)
C5 C6 C7 C8 -0.9(6)
C6 C7 C8 C9 0.2(6)
C5 C4 C9 C8 -1.6(5)
C3 C4 C9 C8 176.7(3)
C7 C8 C9 C4 1.0(5)
C4 C3 C10 C15 169.9(3)
N2 C3 C10 C15 -64.7(4)
C4 C3 C10 C11 -7.0(4)
N2 C3 C10 C11 118.4(3)
C15 C10 C11 C12 0.4(5)
C3 C10 C11 C12 177.4(3)
C10 C11 C12 C13 0.6(6)
C11 C12 C13 C14 -1.2(6)
C12 C13 C14 C15 0.7(6)
C13 C14 C15 C10 0.3(6)
C11 C10 C15 C14 -0.9(5)
C3 C10 C15 C14 -178.0(3)
N2 C1 C16 O17 -50.5(3)
C24 C1 C16 O17 -172.5(2)
N2 C1 C16 C18 -172.8(2)
C24 C1 C16 C18 65.1(3)
O17 C16 C18 C19 121.9(3)
C1 C16 C18 C19 -116.1(3)
O17 C16 C18 C23 -59.7(4)
C1 C16 C18 C23 62.3(4)
C23 C18 C19 C20 -0.1(5)
C16 C18 C19 C20 178.3(3)
C18 C19 C20 C21 -0.5(5)
C19 C20 C21 C22 0.3(5)
C20 C21 C22 C23 0.6(5)
C19 C18 C23 C22 1.0(5)
C16 C18 C23 C22 -177.4(3)
C21 C22 C23 C18 -1.2(6)
N2 C1 C24 O25 -39.4(4)
C16 C1 C24 O25 82.9(4)
N2 C1 C24 O26 143.1(3)
C16 C1 C24 O26 -94.7(3)
O25 C24 O26 C27 -3.2(5)
C1 C24 O26 C27 174.2(3)
C24 O26 C27 C28 -156.3(7)
O32 C30 C33 F34 98.4(5)
O31 C30 C33 F34 -81.2(5)
O32 C30 C33 F36 -138.6(4)
O31 C30 C33 F36 41.8(5)
O32 C30 C33 F35 -26.2(5)
O31 C30 C33 F35 154.2(4)
