#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/23/7102383.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_7102383
loop_
_publ_author_name
'Santoro, Stefano'
'Poulsen, Thomas B'
'Jørgensen, Karl Anker'
_publ_section_title
;
 Enantioselective organocatalytic substitution of alpha-cyanoacetates
 on imidoyl chlorides--synthesis of optically active ketimines.
;
_journal_issue                   48
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5155
_journal_page_last               5157
_journal_paper_doi               10.1039/b715810f
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H18 F3 N3 O5'
_chemical_formula_sum            'C20 H18 F3 N3 O5'
_chemical_formula_weight         437.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2007-09-20T11:08:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2352(4)
_cell_length_b                   14.0673(5)
_cell_length_c                   17.2845(8)
_cell_measurement_reflns_used    2920
_cell_measurement_temperature    91(1)
_cell_measurement_theta_max      64.31
_cell_measurement_theta_min      5.12
_cell_measurement_wavelength     0.71073
_cell_volume                     2002.36(15)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_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      91(1)
_diffrn_detector_area_resol_mean 0.0833
_diffrn_measured_fraction_theta_full 0.813
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       'φ-scans and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2538
_diffrn_reflns_reduction_process
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        65.31
_diffrn_reflns_theta_max         65.31
_diffrn_reflns_theta_min         4.05
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 928 Friedel pairs'
_refine_ls_abs_structure_Flack   0.08(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.031
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0503P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                2398
_reflns_number_total             2538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715810f.txt
_cod_data_source_block           07jo0042_0m
_cod_database_code               7102383
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.4277(3) 0.25447(14) 0.10214(14) 0.0187(5) Uani 1 1 d .
C2 C 0.4007(3) 0.16834(14) 0.06572(13) 0.0226(6) Uani 1 1 d .
H2 H 0.4877 0.1333 0.0467 0.027 Uiso 1 1 calc R
C3 C 0.2446(3) 0.13474(14) 0.05775(13) 0.0257(6) Uani 1 1 d .
H3 H 0.226 0.0764 0.0341 0.031 Uiso 1 1 calc R
C4 C 0.1156(3) 0.18778(14) 0.08495(13) 0.0234(6) Uani 1 1 d .
H4 H 0.0101 0.166 0.0778 0.028 Uiso 1 1 calc R
C5 C 0.1421(3) 0.27354(14) 0.12293(14) 0.0214(6) Uani 1 1 d .
H5 H 0.0545 0.3074 0.1427 0.026 Uiso 1 1 calc R
C6 C 0.2990(3) 0.30896(13) 0.13147(13) 0.0177(5) Uani 1 1 d .
C7 C 0.2867(3) 0.47243(13) 0.16583(13) 0.0174(5) Uani 1 1 d .
C8 C 0.2195(3) 0.50515(14) 0.08843(14) 0.0223(6) Uani 1 1 d .
C9 C 0.3067(3) 0.54716(12) 0.22931(13) 0.0161(5) Uani 1 1 d .
C10 C 0.3953(3) 0.50403(14) 0.29497(15) 0.0193(5) Uani 1 1 d .
C11 C 0.1398(3) 0.58315(13) 0.25978(14) 0.0200(5) Uani 1 1 d .
H11A H 0.1583 0.6286 0.301 0.024 Uiso 1 1 calc R
H11B H 0.0838 0.6159 0.2183 0.024 Uiso 1 1 calc R
C12 C 0.0340(3) 0.50554(14) 0.28930(14) 0.0196(6) Uani 1 1 d .
C13 C 0.0272(3) 0.45550(15) 0.35506(15) 0.0261(6) Uani 1 1 d .
H13 H 0.0926 0.4637 0.3984 0.031 Uiso 1 1 calc R
C14 C -0.0992(3) 0.38719(14) 0.34606(14) 0.0242(6) Uani 1 1 d .
H14 H -0.1328 0.3427 0.3825 0.029 Uiso 1 1 calc R
C15 C -0.1598(3) 0.39954(15) 0.27526(15) 0.0292(6) Uani 1 1 d .
H15 H -0.2441 0.3642 0.2539 0.035 Uiso 1 1 calc R
C16 C 0.4122(3) 0.63220(13) 0.20146(13) 0.0200(6) Uani 1 1 d .
C17 C 0.6401(3) 0.66840(14) 0.11466(14) 0.0205(6) Uani 1 1 d .
C18 C 0.7363(3) 0.60039(14) 0.06452(14) 0.0268(6) Uani 1 1 d .
H18A H 0.8196 0.6348 0.0376 0.04 Uiso 1 1 calc R
H18B H 0.665 0.5709 0.0277 0.04 Uiso 1 1 calc R
H18C H 0.7851 0.5525 0.0965 0.04 Uiso 1 1 calc R
C19 C 0.7439(3) 0.71203(15) 0.17794(15) 0.0263(6) Uani 1 1 d .
H19A H 0.6811 0.7579 0.2061 0.039 Uiso 1 1 calc R
H19B H 0.8364 0.7427 0.1552 0.039 Uiso 1 1 calc R
H19C H 0.78 0.663 0.2126 0.039 Uiso 1 1 calc R
C20 C 0.5500(3) 0.74121(15) 0.06663(15) 0.0290(7) Uani 1 1 d .
H20A H 0.4858 0.7808 0.1 0.043 Uiso 1 1 calc R
H20B H 0.4803 0.7093 0.0305 0.043 Uiso 1 1 calc R
H20C H 0.6266 0.7798 0.0389 0.043 Uiso 1 1 calc R
N1 N 0.4598(3) 0.47535(12) 0.34885(13) 0.0265(5) Uani 1 1 d .
N2 N 0.3258(2) 0.38775(11) 0.18059(11) 0.0169(5) Uani 1 1 d .
N3 N 0.5941(3) 0.28730(12) 0.10848(11) 0.0219(5) Uani 1 1 d .
O1 O 0.7044(2) 0.22921(10) 0.10050(10) 0.0295(4) Uani 1 1 d .
O2 O 0.6180(2) 0.37267(10) 0.12098(9) 0.0264(4) Uani 1 1 d .
O3 O 0.51920(19) 0.60188(9) 0.15095(9) 0.0190(4) Uani 1 1 d .
O4 O 0.3923(2) 0.71190(9) 0.22589(9) 0.0263(4) Uani 1 1 d .
O5 O -0.0793(2) 0.47240(10) 0.23838(9) 0.0282(4) Uani 1 1 d .
F1 F 0.20486(18) 0.60000(8) 0.08348(8) 0.0285(4) Uani 1 1 d .
F2 F 0.07178(17) 0.46965(8) 0.07431(8) 0.0277(3) Uani 1 1 d .
F3 F 0.31547(18) 0.47734(9) 0.03028(8) 0.0324(4) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C2 C1 C6 121.5(2)
C2 C1 N3 117.7(2)
C6 C1 N3 120.82(19)
C3 C2 C1 119.7(2)
C3 C2 H2 120.1
C1 C2 H2 120.1
C2 C3 C4 119.9(2)
C2 C3 H3 120
C4 C3 H3 120
C3 C4 C5 120.6(2)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 120.4(2)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 117.85(18)
C5 C6 N2 119.3(2)
C1 C6 N2 121.9(2)
N2 C7 C8 123.91(19)
N2 C7 C9 118.51(19)
C8 C7 C9 117.58(17)
F3 C8 F2 106.93(18)
F3 C8 F1 107.21(18)
F2 C8 F1 106.14(18)
F3 C8 C7 110.96(18)
F2 C8 C7 112.27(19)
F1 C8 C7 112.95(18)
C10 C9 C7 108.77(16)
C10 C9 C16 106.11(19)
C7 C9 C16 111.55(18)
C10 C9 C11 108.01(19)
C7 C9 C11 111.80(18)
C16 C9 C11 110.35(15)
N1 C10 C9 175.4(2)
C12 C11 C9 113.24(16)
C12 C11 H11A 108.9
C9 C11 H11A 108.9
C12 C11 H11B 108.9
C9 C11 H11B 108.9
H11A C11 H11B 107.7
C13 C12 O5 109.84(19)
C13 C12 C11 134.6(2)
O5 C12 C11 115.5(2)
C12 C13 C14 107.0(2)
C12 C13 H13 126.5
C14 C13 H13 126.5
C15 C14 C13 106.6(2)
C15 C14 H14 126.7
C13 C14 H14 126.7
C14 C15 O5 110.0(2)
C14 C15 H15 125
O5 C15 H15 125
O4 C16 O3 128.7(2)
O4 C16 C9 122.0(2)
O3 C16 C9 109.34(16)
O3 C17 C20 108.98(18)
O3 C17 C18 101.07(15)
C20 C17 C18 111.7(2)
O3 C17 C19 108.90(18)
C20 C17 C19 113.45(18)
C18 C17 C19 111.9(2)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C7 N2 C6 125.43(19)
O1 N3 O2 123.2(2)
O1 N3 C1 118.56(17)
O2 N3 C1 118.26(19)
C16 O3 C17 121.36(15)
C12 O5 C15 106.56(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.383(3)
C1 C6 1.402(3)
C1 N3 1.450(3)
C2 C3 1.377(4)
C2 H2 0.93
C3 C4 1.380(3)
C3 H3 0.93
C4 C5 1.391(3)
C4 H4 0.93
C5 C6 1.393(3)
C5 H5 0.93
C6 N2 1.414(3)
C7 N2 1.260(2)
C7 C8 1.519(3)
C7 C9 1.528(3)
C8 F3 1.337(3)
C8 F2 1.337(3)
C8 F1 1.342(2)
C9 C10 1.479(3)
C9 C16 1.555(3)
C9 C11 1.557(3)
C10 N1 1.145(3)
C11 C12 1.487(3)
C11 H11A 0.97
C11 H11B 0.97
C12 C13 1.338(3)
C12 O5 1.365(3)
C13 C14 1.425(3)
C13 H13 0.93
C14 C15 1.333(3)
C14 H14 0.93
C15 O5 1.377(3)
C15 H15 0.93
C16 O4 1.209(2)
C16 O3 1.312(3)
C17 O3 1.504(3)
C17 C20 1.513(3)
C17 C18 1.514(3)
C17 C19 1.518(3)
C18 H18A 0.96
C18 H18B 0.96
C18 H18C 0.96
C19 H19A 0.96
C19 H19B 0.96
C19 H19C 0.96
C20 H20A 0.96
C20 H20B 0.96
C20 H20C 0.96
N3 O1 1.230(2)
N3 O2 1.236(2)
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
C6 C1 C2 C3 0.0(3)
N3 C1 C2 C3 -179.4(2)
C1 C2 C3 C4 1.1(3)
C2 C3 C4 C5 -2.3(3)
C3 C4 C5 C6 2.5(4)
C4 C5 C6 C1 -1.3(3)
C4 C5 C6 N2 -169.9(2)
C2 C1 C6 C5 0.1(3)
N3 C1 C6 C5 179.5(2)
C2 C1 C6 N2 168.4(2)
N3 C1 C6 N2 -12.2(3)
N2 C7 C8 F3 -52.2(3)
C9 C7 C8 F3 128.2(2)
N2 C7 C8 F2 67.4(3)
C9 C7 C8 F2 -112.2(2)
N2 C7 C8 F1 -172.6(2)
C9 C7 C8 F1 7.7(3)
N2 C7 C9 C10 8.6(3)
C8 C7 C9 C10 -171.76(19)
N2 C7 C9 C16 125.3(2)
C8 C7 C9 C16 -55.1(3)
N2 C7 C9 C11 -110.6(2)
C8 C7 C9 C11 69.0(3)
C10 C9 C11 C12 -62.9(2)
C7 C9 C11 C12 56.7(3)
C16 C9 C11 C12 -178.53(19)
C9 C11 C12 C13 79.1(3)
C9 C11 C12 O5 -97.3(2)
O5 C12 C13 C14 -0.8(3)
C11 C12 C13 C14 -177.3(2)
C12 C13 C14 C15 0.6(3)
C13 C14 C15 O5 -0.2(3)
C10 C9 C16 O4 -92.3(3)
C7 C9 C16 O4 149.4(2)
C11 C9 C16 O4 24.5(3)
C10 C9 C16 O3 87.1(2)
C7 C9 C16 O3 -31.2(3)
C11 C9 C16 O3 -156.13(19)
C8 C7 N2 C6 -6.7(4)
C9 C7 N2 C6 173.0(2)
C5 C6 N2 C7 -73.3(3)
C1 C6 N2 C7 118.5(3)
C2 C1 N3 O1 -18.7(3)
C6 C1 N3 O1 161.9(2)
C2 C1 N3 O2 160.71(19)
C6 C1 N3 O2 -18.8(3)
O4 C16 O3 C17 0.2(4)
C9 C16 O3 C17 -179.12(18)
C20 C17 O3 C16 -64.0(3)
C18 C17 O3 C16 178.2(2)
C19 C17 O3 C16 60.2(2)
C13 C12 O5 C15 0.7(2)
C11 C12 O5 C15 177.90(18)
C14 C15 O5 C12 -0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21196172
