#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024566.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_4024566
loop_
_publ_author_name
'Franca M. Cordero'
'Maria Salvati'
'Carolina Vurchio'
'Armin de Meijere'
'Alberto Brandi'
_publ_contact_author_address
;
University of Florence
Department  of Organic Chemistry ?Ugo Schiff? and HeteroBioLab
Via della Lastruccia 13
50019 Sesto Fiorentino (FI)
Italy 
;
_publ_contact_author_email       franca.cordero@unifi.it
_publ_contact_author_name        'Prof.ssa Franca Cordero'
_publ_section_title
;
Synthesis of α-Cyclopropyl-β-homoprolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4225
_journal_page_last               4231
_journal_paper_doi               10.1021/jo9004684
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C13 H16 F3 N O5'
_chemical_formula_weight         323.27
_chemical_melting_point          390
_chemical_name_systematic
;
1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(trifluoroacetyl)tetrahydro-3aH-
[1,3]dioxolo[4,5-c]pyrrol-4-yl]cyclopropanecarboxylic Acid
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Tue Feb 24 11:50:53 2009'
;
_audit_creation_method
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0340(10)
_cell_length_b                   25.6730(10)
_cell_length_c                   8.0660(10)
_cell_measurement_reflns_used    1394
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7669
_cell_measurement_theta_min      5.1676
_cell_volume                     1456.6(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    Ortep3
_computing_publication_material  Encifer
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir2004
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Xcalibur CuKα (Oxford Diffraction)'
_diffrn_measurement_method       'profile data from omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3494
_diffrn_reflns_theta_full        72.94
_diffrn_reflns_theta_max         72.94
_diffrn_reflns_theta_min         5.48
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 300
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  0.9085
_exptl_absorpt_correction_T_min  0.8353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 'Diethyl ether and petroleum ether'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       0.0180(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0392
_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)+(0.0683P)²+0.8724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                1604
_reflns_number_total             2147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9004684_si_003.cif
_cod_data_source_block           compound16
_cod_database_code               4024566
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6301(4) 0.35595(11) 0.2210(4) 0.0454(7) Uani 1 1 d . . .
O1 O 0.2782(3) 0.37158(8) 0.5098(3) 0.0514(7) Uani 1 1 d . . .
O2 O 0.5292(3) 0.42775(9) 0.4924(4) 0.0605(8) Uani 1 1 d . . .
O3 O 0.5332(4) 0.36507(12) -0.0449(4) 0.0707(8) Uani 1 1 d . . .
O4 O 0.7080(4) 0.25360(9) 0.3834(4) 0.0634(8) Uani 1 1 d . . .
O5 O 0.5360(4) 0.18798(9) 0.2831(4) 0.0665(8) Uani 1 1 d . . .
H5 H 0.6193 0.1706 0.3277 0.100 Uiso 1 1 calc R . .
F1 F 0.9869(4) 0.38128(11) 0.0711(4) 0.0852(8) Uani 1 1 d . . .
F2 F 0.8376(5) 0.41221(11) -0.1389(3) 0.0924(10) Uani 1 1 d . . .
F3 F 0.8249(4) 0.45147(9) 0.0941(4) 0.0870(9) Uani 1 1 d . . .
C1 C 0.4509(5) 0.33126(12) 0.2747(4) 0.0414(8) Uani 1 1 d . . .
C2 C 0.4414(5) 0.34168(13) 0.4621(5) 0.0448(8) Uani 1 1 d . . .
C3 C 0.6089(5) 0.37668(13) 0.5026(5) 0.0463(9) Uani 1 1 d . . .
C4 C 0.7500(5) 0.36985(14) 0.3655(5) 0.0500(9) Uani 1 1 d . . .
H4A H 0.8196 0.4018 0.3454 0.060 Uiso 1 1 calc R . .
H4B H 0.8395 0.3422 0.3910 0.060 Uiso 1 1 calc R . .
C5 C 0.3314(5) 0.42612(12) 0.5196(5) 0.0515(9) Uani 1 1 d . . .
C6 C 0.2397(8) 0.45557(16) 0.3788(7) 0.0902(17) Uani 1 1 d . . .
H6A H 0.1041 0.4553 0.3926 0.135 Uiso 1 1 calc R . .
H6B H 0.2721 0.4393 0.2755 0.135 Uiso 1 1 calc R . .
H6C H 0.2845 0.4909 0.3788 0.135 Uiso 1 1 calc R . .
C7 C 0.2814(8) 0.44582(17) 0.6885(6) 0.0828(15) Uani 1 1 d . . .
H7A H 0.1461 0.4442 0.7035 0.124 Uiso 1 1 calc R . .
H7B H 0.3231 0.4812 0.6996 0.124 Uiso 1 1 calc R . .
H7C H 0.3428 0.4247 0.7708 0.124 Uiso 1 1 calc R . .
C8 C 0.4300(5) 0.27395(12) 0.2320(4) 0.0423(8) Uani 1 1 d . . .
C9 C 0.3442(5) 0.25892(15) 0.0654(5) 0.0544(9) Uani 1 1 d . . .
H9A H 0.3138 0.2868 -0.0115 0.065 Uiso 1 1 calc R . .
H9B H 0.3883 0.2270 0.0140 0.065 Uiso 1 1 calc R . .
C10 C 0.2272(5) 0.25436(14) 0.2175(5) 0.0540(10) Uani 1 1 d . . .
H10A H 0.2000 0.2196 0.2584 0.065 Uiso 1 1 calc R . .
H10B H 0.1255 0.2794 0.2330 0.065 Uiso 1 1 calc R . .
C11 C 0.5719(5) 0.23841(13) 0.3063(5) 0.0485(9) Uani 1 1 d . . .
C12 C 0.6486(5) 0.37300(13) 0.0658(5) 0.0485(8) Uani 1 1 d . . .
C13 C 0.8273(7) 0.40442(15) 0.0240(5) 0.0633(11) Uani 1 1 d . . .
H3 H 0.672(5) 0.3703(14) 0.625(5) 0.052(10) Uiso 1 1 d . . .
H1 H 0.351(5) 0.3496(13) 0.217(4) 0.039(9) Uiso 1 1 d . . .
H2 H 0.444(5) 0.3092(14) 0.519(4) 0.045(9) 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 N1 C1 120.0(3) . . ?
C12 N1 C4 127.2(3) . . ?
C1 N1 C4 111.0(3) . . ?
C2 O1 C5 108.9(2) . . ?
C5 O2 C3 110.6(3) . . ?
C11 O5 H5 109.5 . . ?
N1 C1 C8 115.6(3) . . ?
N1 C1 C2 104.5(3) . . ?
C8 C1 C2 112.8(3) . . ?
N1 C1 H1 105.9(19) . . ?
C8 C1 H1 107.0(19) . . ?
C2 C1 H1 111(2) . . ?
O1 C2 C3 104.3(2) . . ?
O1 C2 C1 113.1(3) . . ?
C3 C2 C1 106.3(3) . . ?
O1 C2 H2 111(2) . . ?
C3 C2 H2 114(2) . . ?
C1 C2 H2 109(2) . . ?
O2 C3 C4 109.0(3) . . ?
O2 C3 C2 103.1(3) . . ?
C4 C3 C2 106.7(3) . . ?
O2 C3 H3 110.4(19) . . ?
C4 C3 H3 112.4(19) . . ?
C2 C3 H3 115(2) . . ?
N1 C4 C3 103.4(3) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
O2 C5 O1 106.0(3) . . ?
O2 C5 C7 111.3(4) . . ?
O1 C5 C7 108.4(3) . . ?
O2 C5 C6 106.9(4) . . ?
O1 C5 C6 109.4(3) . . ?
C7 C5 C6 114.6(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C8 C10 117.5(3) . . ?
C11 C8 C1 116.1(3) . . ?
C10 C8 C1 115.5(3) . . ?
C11 C8 C9 117.9(3) . . ?
C10 C8 C9 58.3(2) . . ?
C1 C8 C9 119.0(3) . . ?
C10 C9 C8 60.6(2) . . ?
C10 C9 H9A 117.7 . . ?
C8 C9 H9A 117.7 . . ?
C10 C9 H9B 117.7 . . ?
C8 C9 H9B 117.7 . . ?
H9A C9 H9B 114.8 . . ?
C9 C10 C8 61.0(2) . . ?
C9 C10 H10A 117.7 . . ?
C8 C10 H10A 117.7 . . ?
C9 C10 H10B 117.7 . . ?
C8 C10 H10B 117.7 . . ?
H10A C10 H10B 114.8 . . ?
O4 C11 O5 122.5(3) . . ?
O4 C11 C8 123.0(3) . . ?
O5 C11 C8 114.5(3) . . ?
O3 C12 N1 124.5(3) . . ?
O3 C12 C13 118.1(3) . . ?
N1 C12 C13 117.4(3) . . ?
F1 C13 F2 107.7(4) . . ?
F1 C13 F3 107.1(4) . . ?
F2 C13 F3 106.4(3) . . ?
F1 C13 C12 113.3(3) . . ?
F2 C13 C12 110.0(4) . . ?
F3 C13 C12 111.9(3) . . ?
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
N1 C12 1.333(5) . ?
N1 C1 1.476(4) . ?
N1 C4 1.482(5) . ?
O1 C2 1.434(4) . ?
O1 C5 1.452(4) . ?
O2 C5 1.409(4) . ?
O2 C3 1.428(4) . ?
O3 C12 1.224(5) . ?
O4 C11 1.206(4) . ?
O5 C11 1.332(4) . ?
O5 H5 0.8200 . ?
F1 C13 1.326(5) . ?
F2 C13 1.331(5) . ?
F3 C13 1.334(4) . ?
C1 C8 1.518(5) . ?
C1 C2 1.537(5) . ?
C1 H1 0.96(3) . ?
C2 C3 1.517(5) . ?
C2 H2 0.95(4) . ?
C3 C4 1.496(5) . ?
C3 H3 1.09(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.495(6) . ?
C5 C6 1.509(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C11 1.479(5) . ?
C8 C10 1.517(5) . ?
C8 C9 1.523(5) . ?
C9 C10 1.482(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.531(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658959
