#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:08:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178422 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/43/4024343.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_4024343
loop_
_publ_author_name
'Javier Carreras'
'Alberto Avenoza'
'Jesús H. Busto'
'Jesús M. Peregrina'
_publ_section_title
;
A Highly Regioselective Ring-Opening Metathesis-Cross Metathesis Process
Modulated by the Electronic Effects of the Cross Metathesis Partner: An
Entry to Quaternary Prolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1736
_journal_page_last               1739
_journal_paper_doi               10.1021/jo802399k
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H23 F3 N O3 S'
_chemical_formula_sum            'C18 H24 F3 N O4 S'
_chemical_formula_weight         407.44
_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                111.883(3)
_cell_angle_beta                 90.183(2)
_cell_angle_gamma                102.146(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3859(5)
_cell_length_b                   10.6390(6)
_cell_length_c                   10.8902(6)
_cell_measurement_reflns_used    2557
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.21
_cell_volume                     982.51(9)
_computing_cell_refinement       'Denzo and Scalepak (1997)'
_computing_data_collection       'Nonius Kappa CCD'
_computing_data_reduction        'Denzo and Scalepak (1997)'
_computing_molecular_graphics    'ORTEP III'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8627
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     refxyz
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0573
_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)+(0.0610P)²+0.4213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                2856
_reflns_number_total             4262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802399k_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024343
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33252(7) 0.06055(8) 0.18720(8) 0.0616(2) Uani 1 1 d . . .
N2 N 0.7043(2) 0.3773(2) 0.5145(2) 0.0417(5) Uani 1 1 d . . .
C3 C 0.7954(3) 0.4434(3) 0.6463(2) 0.0443(6) Uani 1 1 d . . .
C4 C 0.8266(3) 0.2062(3) 0.3656(3) 0.0467(6) Uani 1 1 d . . .
O5 O 0.8229(2) 0.07144(18) 0.3019(2) 0.0615(5) Uani 1 1 d . . .
C6 C 0.7052(2) 0.2252(2) 0.4585(2) 0.0426(5) Uani 1 1 d . . .
C7 C 0.5562(3) 0.1370(3) 0.3867(3) 0.0458(6) Uani 1 1 d . . .
C8 C 0.2852(3) 0.3758(3) 0.6053(3) 0.0468(6) Uani 1 1 d . . .
O9 O 0.1946(2) 0.4456(2) 0.6116(2) 0.0708(6) Uani 1 1 d . . .
O10 O 0.9132(2) 0.29770(19) 0.3517(2) 0.0702(6) Uani 1 1 d . . .
O11 O 0.4096(2) 0.3923(2) 0.5721(2) 0.0717(6) Uani 1 1 d . . .
C12 C 0.5102(3) 0.1644(3) 0.2670(3) 0.0524(6) Uani 1 1 d . . .
C13 C 0.3621(3) -0.1069(3) 0.0968(2) 0.0488(6) Uani 1 1 d . . .
C14 C 0.2302(3) 0.2503(3) 0.6424(3) 0.0577(7) Uani 1 1 d . . .
C15 C 0.7575(3) 0.5788(3) 0.7305(3) 0.0548(7) Uani 1 1 d . . .
C16 C 0.2398(3) -0.2073(3) 0.0238(3) 0.0590(7) Uani 1 1 d . . .
C17 C 0.4953(3) -0.1441(3) 0.0939(3) 0.0566(7) Uani 1 1 d . . .
C18 C 0.7450(4) 0.1945(3) 0.5805(3) 0.0570(7) Uani 1 1 d . . .
C19 C 0.5042(4) -0.2796(3) 0.0195(3) 0.0658(8) Uani 1 1 d . . .
C20 C 0.8483(4) 0.6478(4) 0.8633(3) 0.0639(8) Uani 1 1 d . . .
F21 F 0.1429(3) 0.1482(2) 0.5487(2) 0.1149(9) Uani 1 1 d . . .
C22 C 0.2511(4) -0.3412(3) -0.0511(3) 0.0677(8) Uani 1 1 d . . .
C23 C 0.3837(4) -0.3776(3) -0.0521(3) 0.0666(8) Uani 1 1 d . . .
C24 C 0.9390(4) 0.0377(3) 0.2171(4) 0.0786(10) Uani 1 1 d . . .
H24A H 0.9260 -0.0615 0.1768 0.118 Uiso 1 1 calc R . .
H24B H 1.0318 0.0778 0.2692 0.118 Uiso 1 1 calc R . .
H24C H 0.9364 0.0745 0.1491 0.118 Uiso 1 1 calc R . .
F25 F 0.1588(3) 0.2785(2) 0.7484(2) 0.1167(9) Uani 1 1 d . . .
C26 C 0.7584(4) 0.3278(3) 0.6987(3) 0.0625(8) Uani 1 1 d . . .
F27 F 0.3369(3) 0.1974(3) 0.6679(3) 0.1153(9) Uani 1 1 d . . .
H22 H 0.167(4) -0.408(3) -0.103(3) 0.077(10) Uiso 1 1 d . . .
H19 H 0.598(4) -0.304(3) 0.026(3) 0.082(10) Uiso 1 1 d . . .
H23 H 0.397(4) -0.467(4) -0.103(3) 0.084(10) Uiso 1 1 d . . .
H7A H 0.482(3) 0.151(3) 0.448(3) 0.049(7) Uiso 1 1 d . . .
H12A H 0.499(3) 0.263(3) 0.295(3) 0.059(8) Uiso 1 1 d . . .
H12B H 0.578(3) 0.152(3) 0.203(3) 0.060(8) Uiso 1 1 d . . .
H20C H 0.830(3) 0.592(3) 0.913(3) 0.061(9) Uiso 1 1 d . . .
H20B H 0.824(3) 0.740(3) 0.915(3) 0.071(9) Uiso 1 1 d . . .
H20A H 0.951(4) 0.662(3) 0.850(3) 0.077(10) Uiso 1 1 d . . .
H15B H 0.774(3) 0.646(3) 0.676(3) 0.078(10) Uiso 1 1 d . . .
H15A H 0.659(4) 0.563(3) 0.744(3) 0.069(9) Uiso 1 1 d . . .
H2A H 0.614(3) 0.387(3) 0.531(3) 0.049(7) Uiso 1 1 d . . .
H16 H 0.154(3) -0.180(3) 0.030(3) 0.071(9) Uiso 1 1 d . . .
H26B H 0.829(3) 0.341(3) 0.763(3) 0.068(9) Uiso 1 1 d . . .
H3 H 0.894(3) 0.457(3) 0.625(3) 0.066(9) Uiso 1 1 d . . .
H26A H 0.653(4) 0.327(4) 0.738(4) 0.108(13) Uiso 1 1 d . . .
H7B H 0.562(3) 0.042(3) 0.361(3) 0.052(7) Uiso 1 1 d . . .
H2B H 0.740(3) 0.425(3) 0.461(3) 0.059(8) Uiso 1 1 d . . .
H18B H 0.833(4) 0.165(4) 0.571(4) 0.093(12) Uiso 1 1 d . . .
H18A H 0.676(4) 0.117(4) 0.584(3) 0.080(10) Uiso 1 1 d . . .
H17 H 0.577(3) -0.073(3) 0.139(3) 0.065(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 0.0033 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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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
C13 S1 C12 104.79(13) . . ?
C6 N2 C3 107.70(19) . . ?
C6 N2 H2A 109.3(17) . . ?
C3 N2 H2A 106.7(17) . . ?
C6 N2 H2B 114.4(17) . . ?
C3 N2 H2B 108.9(17) . . ?
H2A N2 H2B 109(2) . . ?
C15 C3 N2 110.8(2) . . ?
C15 C3 C26 115.8(2) . . ?
N2 C3 C26 101.0(2) . . ?
C15 C3 H3 111.8(18) . . ?
N2 C3 H3 105.1(18) . . ?
C26 C3 H3 111.3(18) . . ?
O10 C4 O5 124.4(2) . . ?
O10 C4 C6 125.3(2) . . ?
O5 C4 C6 110.3(2) . . ?
C4 O5 C24 116.5(2) . . ?
N2 C6 C4 107.52(19) . . ?
N2 C6 C7 110.92(19) . . ?
C4 C6 C7 111.7(2) . . ?
N2 C6 C18 104.4(2) . . ?
C4 C6 C18 109.5(2) . . ?
C7 C6 C18 112.4(2) . . ?
C12 C7 C6 114.7(2) . . ?
C12 C7 H7A 108.8(15) . . ?
C6 C7 H7A 109.7(15) . . ?
C12 C7 H7B 110.6(16) . . ?
C6 C7 H7B 106.3(16) . . ?
H7A C7 H7B 106(2) . . ?
O11 C8 O9 129.0(3) . . ?
O11 C8 C14 117.0(2) . . ?
O9 C8 C14 114.0(2) . . ?
C7 C12 S1 113.25(19) . . ?
C7 C12 H12A 110.5(16) . . ?
S1 C12 H12A 104.0(16) . . ?
C7 C12 H12B 112.9(18) . . ?
S1 C12 H12B 109.0(18) . . ?
H12A C12 H12B 107(2) . . ?
C17 C13 C16 118.8(3) . . ?
C17 C13 S1 125.3(2) . . ?
C16 C13 S1 116.0(2) . . ?
F21 C14 F25 106.3(3) . . ?
F21 C14 F27 105.4(3) . . ?
F25 C14 F27 105.2(3) . . ?
F21 C14 C8 112.9(2) . . ?
F25 C14 C8 113.3(2) . . ?
F27 C14 C8 113.0(2) . . ?
C3 C15 C20 111.8(2) . . ?
C3 C15 H15B 108.3(17) . . ?
C20 C15 H15B 110.5(17) . . ?
C3 C15 H15A 109.4(19) . . ?
C20 C15 H15A 109.6(19) . . ?
H15B C15 H15A 107(3) . . ?
C22 C16 C13 120.6(3) . . ?
C22 C16 H16 123(2) . . ?
C13 C16 H16 116(2) . . ?
C13 C17 C19 119.8(3) . . ?
C13 C17 H17 116.8(18) . . ?
C19 C17 H17 123.3(18) . . ?
C26 C18 C6 106.1(2) . . ?
C26 C18 H18B 111(2) . . ?
C6 C18 H18B 110(2) . . ?
C26 C18 H18A 115(2) . . ?
C6 C18 H18A 111(2) . . ?
H18B C18 H18A 103(3) . . ?
C23 C19 C17 121.1(3) . . ?
C23 C19 H19 121(2) . . ?
C17 C19 H19 117(2) . . ?
C15 C20 H20C 111.1(18) . . ?
C15 C20 H20B 109.9(18) . . ?
H20C C20 H20B 109(2) . . ?
C15 C20 H20A 110.3(19) . . ?
H20C C20 H20A 107(3) . . ?
H20B C20 H20A 110(3) . . ?
C23 C22 C16 120.2(3) . . ?
C23 C22 H22 120(2) . . ?
C16 C22 H22 120(2) . . ?
C19 C23 C22 119.5(3) . . ?
C19 C23 H23 117(2) . . ?
C22 C23 H23 123(2) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C26 C3 106.1(2) . . ?
C18 C26 H26B 113(2) . . ?
C3 C26 H26B 110(2) . . ?
C18 C26 H26A 108(2) . . ?
C3 C26 H26A 109(2) . . ?
H26B C26 H26A 110(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
S1 C13 1.767(3) . ?
S1 C12 1.805(3) . ?
N2 C6 1.503(3) . ?
N2 C3 1.508(3) . ?
N2 H2A 0.89(3) . ?
N2 H2B 0.93(3) . ?
C3 C15 1.508(4) . ?
C3 C26 1.517(4) . ?
C3 H3 0.95(3) . ?
C4 O10 1.187(3) . ?
C4 O5 1.333(3) . ?
C4 C6 1.521(3) . ?
O5 C24 1.446(3) . ?
C6 C7 1.530(3) . ?
C6 C18 1.545(4) . ?
C7 C12 1.518(4) . ?
C7 H7A 0.96(3) . ?
C7 H7B 0.96(3) . ?
C8 O11 1.220(3) . ?
C8 O9 1.228(3) . ?
C8 C14 1.524(4) . ?
C12 H12A 1.00(3) . ?
C12 H12B 0.94(3) . ?
C13 C17 1.386(4) . ?
C13 C16 1.392(4) . ?
C14 F21 1.298(3) . ?
C14 F25 1.305(3) . ?
C14 F27 1.323(3) . ?
C15 C20 1.514(4) . ?
C15 H15B 1.07(3) . ?
C15 H15A 0.93(3) . ?
C16 C22 1.380(4) . ?
C16 H16 0.90(3) . ?
C17 C19 1.387(4) . ?
C17 H17 0.94(3) . ?
C18 C26 1.499(4) . ?
C18 H18B 0.93(4) . ?
C18 H18A 0.95(3) . ?
C19 C23 1.366(4) . ?
C19 H19 0.97(3) . ?
C20 H20C 0.94(3) . ?
C20 H20B 1.01(3) . ?
C20 H20A 0.97(4) . ?
C22 C23 1.378(5) . ?
C22 H22 0.95(3) . ?
C23 H23 0.94(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 H26B 0.92(3) . ?
C26 H26A 1.08(4) . ?
