#------------------------------------------------------------------------------
#$Date: 2020-07-28 02:06:12 +0300 (Tue, 28 Jul 2020) $
#$Revision: 254604 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038612.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_4038612
loop_
_publ_author_name
'Ben Jamaa, Abdelkhalek'
'Latrache, Mohammed'
'Riguet, Emmanuel'
'Grellepois, Fabienne'
_publ_section_title
;
 cis-Dihydroxylated α-Trifluoromethylated N,O-Acetal from l-Tartaric
 Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective
 Pictet-Spengler Cyclization of N-Acyliminium Ions
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00801
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H18 F3 N O4'
_chemical_formula_weight         345.31
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.260(5)
_cell_length_b                   10.089(5)
_cell_length_c                   18.565(5)
_cell_measurement_reflns_used    9206
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      74.49
_cell_measurement_theta_min      4.99
_cell_volume                     1547.1(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34080
_diffrn_reflns_theta_full        74.48
_diffrn_reflns_theta_max         74.48
_diffrn_reflns_theta_min         4.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0233
_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)+(0.0394P)²+0.2393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0612
_reflns_number_gt                3115
_reflns_number_total             3173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00801_si_002.cif
_cod_data_source_block           cu_14fg008bis_0m
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4038612
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.65110(8) 0.83662(7) 0.56166(4) 0.02376(16) Uani 1 1 d . . .
F2 F 0.90354(8) 0.84522(8) 0.53445(4) 0.02569(16) Uani 1 1 d . . .
F3 F 0.76279(9) 1.02534(7) 0.53972(4) 0.02732(16) Uani 1 1 d . . .
O4 O 1.01437(9) 1.23051(7) 0.69441(4) 0.01713(16) Uani 1 1 d . . .
O3 O 0.85774(9) 0.79756(7) 0.67511(4) 0.01736(16) Uani 1 1 d . . .
O2 O 0.69510(10) 1.18203(7) 0.76426(4) 0.01979(17) Uani 1 1 d . . .
O1 O 0.67480(10) 0.95492(8) 0.76105(4) 0.02054(17) Uani 1 1 d . . .
N1 N 0.96569(10) 1.01509(9) 0.65972(5) 0.01406(18) Uani 1 1 d . . .
C10 C 0.92317(12) 1.13731(10) 0.68326(5) 0.0142(2) Uani 1 1 d . . .
C1 C 1.13744(12) 0.96950(11) 0.65327(6) 0.0153(2) Uani 1 1 d . . .
C011 C 0.78670(14) 0.90735(11) 0.57052(6) 0.0179(2) Uani 1 1 d . . .
C11 C 0.68558(12) 0.99747(10) 0.68858(6) 0.0158(2) Uani 1 1 d . . .
C9 C 0.82752(12) 0.92418(10) 0.65086(6) 0.0144(2) Uani 1 1 d . . .
C12 C 0.73906(13) 1.14146(10) 0.69413(6) 0.0156(2) Uani 1 1 d . . .
C13 C 0.68850(13) 1.06694(10) 0.80937(6) 0.0176(2) Uani 1 1 d . . .
C3 C 1.30512(15) 1.15843(12) 0.59885(7) 0.0242(3) Uani 1 1 d . . .
H3 H 1.2982 1.2043 0.6422 0.029 Uiso 1 1 calc R . .
C2 C 1.22800(13) 1.03585(12) 0.59144(6) 0.0182(2) Uani 1 1 d . . .
C15 C 0.53803(14) 1.07789(14) 0.85535(6) 0.0239(2) Uani 1 1 d . . .
H15A H 0.5465 1.1542 0.8860 0.036 Uiso 1 1 calc R . .
H15B H 0.5272 0.9997 0.8844 0.036 Uiso 1 1 calc R . .
H15C H 0.4448 1.0867 0.8249 0.036 Uiso 1 1 calc R . .
C8 C 1.22258(13) 0.98261(11) 0.72568(6) 0.0176(2) Uani 1 1 d . . .
H8A H 1.2268 1.0743 0.7393 0.026 Uiso 1 1 calc R . .
H8B H 1.3306 0.9483 0.7219 0.026 Uiso 1 1 calc R . .
H8C H 1.1640 0.9335 0.7615 0.026 Uiso 1 1 calc R . .
C7 C 1.24251(14) 0.96879(15) 0.52631(7) 0.0294(3) Uani 1 1 d . . .
H7 H 1.1939 0.8862 0.5210 0.035 Uiso 1 1 calc R . .
C14 C 0.84143(15) 1.05101(12) 0.85358(7) 0.0234(2) Uani 1 1 d . . .
H14A H 0.9338 1.0512 0.8222 0.035 Uiso 1 1 calc R . .
H14B H 0.8373 0.9687 0.8794 0.035 Uiso 1 1 calc R . .
H14C H 0.8501 1.1231 0.8871 0.035 Uiso 1 1 calc R . .
C6 C 1.32833(15) 1.02303(18) 0.46910(7) 0.0369(3) Uani 1 1 d . . .
H6 H 1.3360 0.9772 0.4258 0.044 Uiso 1 1 calc R . .
C4 C 1.39207(17) 1.21214(13) 0.54177(8) 0.0328(3) Uani 1 1 d . . .
H4 H 1.4436 1.2935 0.5473 0.039 Uiso 1 1 calc R . .
C5 C 1.40264(17) 1.14558(16) 0.47665(7) 0.0352(3) Uani 1 1 d . . .
H5 H 1.4591 1.1828 0.4383 0.042 Uiso 1 1 calc R . .
H1 H 1.1268(17) 0.8740(15) 0.6410(8) 0.019(3) Uiso 1 1 d . . .
H11 H 0.5837(17) 0.9826(14) 0.6619(8) 0.017(3) Uiso 1 1 d . . .
H12 H 0.6919(18) 1.2047(14) 0.6596(8) 0.021(3) Uiso 1 1 d . . .
H10 H 0.877(2) 0.7938(19) 0.7207(11) 0.045(5) 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 0.0181 0.0091 '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 0.0311 0.0180 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C13 108.28(8) . . ?
C11 O1 C13 110.34(8) . . ?
C10 N1 C9 113.70(9) . . ?
C10 N1 C1 123.47(9) . . ?
C9 N1 C1 122.29(9) . . ?
O4 C10 N1 126.52(10) . . ?
O4 C10 C12 124.56(10) . . ?
N1 C10 C12 108.92(9) . . ?
N1 C1 C8 109.91(9) . . ?
N1 C1 C2 112.98(9) . . ?
C8 C1 C2 113.57(9) . . ?
F2 C011 F3 108.16(9) . . ?
F2 C011 F1 107.09(9) . . ?
F3 C011 F1 107.40(9) . . ?
F2 C011 C9 112.37(9) . . ?
F3 C011 C9 110.43(9) . . ?
F1 C011 C9 111.19(9) . . ?
O1 C11 C12 104.09(8) . . ?
O1 C11 C9 109.38(8) . . ?
C12 C11 C9 105.42(9) . . ?
O3 C9 N1 113.61(9) . . ?
O3 C9 C011 104.73(9) . . ?
N1 C9 C011 110.28(8) . . ?
O3 C9 C11 115.53(9) . . ?
N1 C9 C11 103.77(9) . . ?
C011 C9 C11 108.92(9) . . ?
O2 C12 C11 105.34(9) . . ?
O2 C12 C10 112.58(9) . . ?
C11 C12 C10 104.64(8) . . ?
O2 C13 O1 105.87(9) . . ?
O2 C13 C15 107.58(9) . . ?
O1 C13 C15 110.04(9) . . ?
O2 C13 C14 111.77(9) . . ?
O1 C13 C14 108.55(9) . . ?
C15 C13 C14 112.79(10) . . ?
C4 C3 C2 120.34(12) . . ?
C7 C2 C3 118.47(11) . . ?
C7 C2 C1 118.89(11) . . ?
C3 C2 C1 122.53(10) . . ?
C6 C7 C2 121.14(13) . . ?
C7 C6 C5 119.96(13) . . ?
C5 C4 C3 120.58(14) . . ?
C4 C5 C6 119.49(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C011 1.3382(14) . ?
F2 C011 1.3313(14) . ?
F3 C011 1.3353(14) . ?
O4 C10 1.2225(14) . ?
O3 C9 1.3773(14) . ?
O2 C12 1.4123(13) . ?
O2 C13 1.4327(14) . ?
O1 C11 1.4150(13) . ?
O1 C13 1.4474(14) . ?
N1 C10 1.3545(15) . ?
N1 C9 1.4734(14) . ?
N1 C1 1.4962(15) . ?
C10 C12 1.5347(17) . ?
C1 C8 1.5228(15) . ?
C1 C2 1.5249(15) . ?
C011 C9 1.5386(14) . ?
C11 C12 1.5218(16) . ?
C11 C9 1.5530(15) . ?
C13 C15 1.5119(17) . ?
C13 C14 1.5149(17) . ?
C3 C4 1.3902(18) . ?
C3 C2 1.3980(17) . ?
C2 C7 1.3906(17) . ?
C7 C6 1.3893(19) . ?
C6 C5 1.388(2) . ?
C4 C5 1.386(2) . ?
