#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151690.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_7151690
loop_
_publ_author_name
'Li, Peng'
'Liu, Li-Juan'
'Liu, Jin-Tao'
_publ_section_title
;
 Per(poly)fluoroalkanesulfinamides assisted diastereoselective
 three-component inverse-electron-demand aza Diels-Alder reaction.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              74
_journal_page_last               77
_journal_paper_doi               10.1039/C0OB00699H
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C14 H11 Cl F7 N O2 S'
_chemical_formula_weight         425.75
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.492(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1841(15)
_cell_length_b                   5.7816(7)
_cell_length_c                   24.406(3)
_cell_measurement_reflns_used    2471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.418
_cell_measurement_theta_min      5.170
_cell_volume                     1695.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8450
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76363
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.223
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1508P)²+0.4758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2257
_refine_ls_wR_factor_ref         0.2394
_reflns_number_gt                2317
_reflns_number_total             3133
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00699H.TXT
_cod_data_source_block           cd29400
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7151690
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.19596(8) 0.05154(17) 0.10981(4) 0.0474(4) Uani 1 1 d . . .
Cl1 Cl 0.16353(16) 0.3050(3) -0.06205(5) 0.1074(7) Uani 1 1 d . . .
F1 F -0.0230(2) 0.2895(7) 0.22699(13) 0.0914(10) Uani 1 1 d . . .
F2 F -0.0142(3) 0.1198(11) 0.15129(18) 0.152(2) Uani 1 1 d . . .
F3 F 0.0099(3) 0.4786(9) 0.15767(18) 0.1378(19) Uani 1 1 d . . .
F4 F 0.0919(3) 0.3602(7) 0.04496(13) 0.1103(13) Uani 1 1 d . . .
F5 F 0.2657(3) 0.4173(6) 0.05811(11) 0.0959(11) Uani 1 1 d . . .
F6 F 0.3020(4) 0.0599(10) -0.00139(19) 0.152(2) Uani 1 1 d . . .
F7 F 0.1365(4) -0.0587(7) -0.00948(14) 0.1257(15) Uani 1 1 d . . .
N1 N 0.2200(2) 0.2542(5) 0.15902(12) 0.0427(7) Uani 1 1 d . . .
O1 O 0.3404(2) 0.5649(5) 0.18947(11) 0.0537(7) Uani 1 1 d . . .
H1 H 0.3127 0.6377 0.1618 0.081 Uiso 1 1 calc R . .
O2 O 0.2964(3) -0.0877(5) 0.10944(12) 0.0623(8) Uani 1 1 d . . .
C1 C 0.3373(3) 0.3289(7) 0.17731(14) 0.0415(8) Uani 1 1 d . . .
H1A H 0.3810 0.2976 0.1478 0.050 Uiso 1 1 calc R . .
C2 C 0.3863(3) 0.1982(7) 0.22949(14) 0.0416(8) Uani 1 1 d . . .
H2A H 0.4642 0.2384 0.2401 0.050 Uiso 1 1 calc R . .
H2B H 0.3814 0.0331 0.2224 0.050 Uiso 1 1 calc R . .
C3 C 0.3226(3) 0.2596(6) 0.27672(14) 0.0412(8) Uani 1 1 d . . .
H3 H 0.3434 0.4182 0.2882 0.049 Uiso 1 1 calc R . .
C4 C 0.1993(3) 0.2607(7) 0.25537(16) 0.0467(9) Uani 1 1 d . . .
H4 H 0.1516 0.2681 0.2814 0.056 Uiso 1 1 calc R . .
C5 C 0.1544(3) 0.2521(7) 0.20280(15) 0.0448(9) Uani 1 1 d . . .
C6 C 0.0324(4) 0.2837(12) 0.1848(2) 0.0778(16) Uani 1 1 d . . .
C7 C 0.3541(3) 0.1084(7) 0.32688(14) 0.0411(8) Uani 1 1 d . . .
C8 C 0.4359(3) 0.1787(8) 0.36942(15) 0.0515(10) Uani 1 1 d . . .
H8 H 0.4704 0.3210 0.3671 0.062 Uiso 1 1 calc R . .
C9 C 0.4676(4) 0.0399(10) 0.41566(17) 0.0667(13) Uani 1 1 d . . .
H9 H 0.5237 0.0880 0.4439 0.080 Uiso 1 1 calc R . .
C10 C 0.4157(4) -0.1687(10) 0.41953(18) 0.0714(14) Uani 1 1 d . . .
H10 H 0.4367 -0.2618 0.4506 0.086 Uiso 1 1 calc R . .
C11 C 0.3340(4) -0.2397(8) 0.37843(19) 0.0657(12) Uani 1 1 d . . .
H11 H 0.2983 -0.3802 0.3815 0.079 Uiso 1 1 calc R . .
C12 C 0.3039(3) -0.1023(7) 0.33176(16) 0.0521(10) Uani 1 1 d . . .
H12 H 0.2489 -0.1533 0.3033 0.063 Uiso 1 1 calc R . .
C13 C 0.1932(4) 0.2544(7) 0.04922(16) 0.0559(11) Uani 1 1 d . . .
C14 C 0.1917(6) 0.1248(12) -0.00441(19) 0.0857(17) 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'
Cl Cl 0.1484 0.1585 '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
O2 S1 N1 110.03(17) . . ?
O2 S1 C13 104.11(19) . . ?
N1 S1 C13 96.10(17) . . ?
C5 N1 C1 113.8(3) . . ?
C5 N1 S1 118.5(2) . . ?
C1 N1 S1 117.7(2) . . ?
C1 O1 H1 109.5 . . ?
O1 C1 N1 109.8(3) . . ?
O1 C1 C2 108.4(3) . . ?
N1 C1 C2 109.4(3) . . ?
O1 C1 H1A 109.7 . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
C1 C2 C3 109.7(3) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C7 C3 C4 113.0(3) . . ?
C7 C3 C2 112.6(3) . . ?
C4 C3 C2 109.9(3) . . ?
C7 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
C2 C3 H3 107.0 . . ?
C5 C4 C3 124.8(3) . . ?
C5 C4 H4 117.6 . . ?
C3 C4 H4 117.6 . . ?
C4 C5 N1 122.3(3) . . ?
C4 C5 C6 121.3(4) . . ?
N1 C5 C6 115.5(3) . . ?
F3 C6 F2 105.8(5) . . ?
F3 C6 F1 106.3(5) . . ?
F2 C6 F1 106.2(5) . . ?
F3 C6 C5 111.7(5) . . ?
F2 C6 C5 113.7(5) . . ?
F1 C6 C5 112.7(4) . . ?
C8 C7 C12 118.2(4) . . ?
C8 C7 C3 119.9(4) . . ?
C12 C7 C3 121.9(3) . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 121.1(4) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
F5 C13 F4 105.8(4) . . ?
F5 C13 C14 114.9(4) . . ?
F4 C13 C14 106.0(4) . . ?
F5 C13 S1 113.7(3) . . ?
F4 C13 S1 103.7(3) . . ?
C14 C13 S1 111.6(4) . . ?
F7 C14 F6 106.1(6) . . ?
F7 C14 C13 115.9(5) . . ?
F6 C14 C13 102.5(4) . . ?
F7 C14 Cl1 113.4(4) . . ?
F6 C14 Cl1 105.4(4) . . ?
C13 C14 Cl1 112.2(4) . . ?
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 O2 1.466(3) . ?
S1 N1 1.669(3) . ?
S1 C13 1.884(4) . ?
Cl1 C14 1.739(6) . ?
F1 C6 1.322(6) . ?
F2 C6 1.317(7) . ?
F3 C6 1.312(7) . ?
F4 C13 1.367(5) . ?
F5 C13 1.285(5) . ?
F6 C14 1.386(7) . ?
F7 C14 1.251(7) . ?
N1 C5 1.436(5) . ?
N1 C1 1.489(4) . ?
O1 C1 1.396(5) . ?
O1 H1 0.8200 . ?
C1 C2 1.516(5) . ?
C1 H1A 0.9800 . ?
C2 C3 1.534(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C7 1.502(5) . ?
C3 C4 1.506(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.310(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.491(6) . ?
C7 C8 1.377(5) . ?
C7 C12 1.377(6) . ?
C8 C9 1.386(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.355(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.506(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 S1 0.82 2.96 3.696(3) 150.6 1_565
O1 H1 O2 0.82 2.03 2.791(4) 154.9 1_565
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C5 -119.3(3) . . . . ?
C13 S1 N1 C5 133.2(3) . . . . ?
O2 S1 N1 C1 24.2(3) . . . . ?
C13 S1 N1 C1 -83.3(3) . . . . ?
C5 N1 C1 O1 -70.5(4) . . . . ?
S1 N1 C1 O1 144.4(2) . . . . ?
C5 N1 C1 C2 48.4(4) . . . . ?
S1 N1 C1 C2 -96.7(3) . . . . ?
O1 C1 C2 C3 56.4(4) . . . . ?
N1 C1 C2 C3 -63.3(4) . . . . ?
C1 C2 C3 C7 170.7(3) . . . . ?
C1 C2 C3 C4 43.7(4) . . . . ?
C7 C3 C4 C5 -138.1(4) . . . . ?
C2 C3 C4 C5 -11.3(5) . . . . ?
C3 C4 C5 N1 -3.8(6) . . . . ?
C3 C4 C5 C6 -172.2(4) . . . . ?
C1 N1 C5 C4 -15.4(5) . . . . ?
S1 N1 C5 C4 129.5(4) . . . . ?
C1 N1 C5 C6 153.7(4) . . . . ?
S1 N1 C5 C6 -61.5(5) . . . . ?
C4 C5 C6 F3 111.2(5) . . . . ?
N1 C5 C6 F3 -57.9(6) . . . . ?
C4 C5 C6 F2 -129.2(5) . . . . ?
N1 C5 C6 F2 61.6(6) . . . . ?
C4 C5 C6 F1 -8.3(7) . . . . ?
N1 C5 C6 F1 -177.5(4) . . . . ?
C4 C3 C7 C8 -141.1(4) . . . . ?
C2 C3 C7 C8 93.6(4) . . . . ?
C4 C3 C7 C12 39.3(5) . . . . ?
C2 C3 C7 C12 -85.9(4) . . . . ?
C12 C7 C8 C9 0.6(6) . . . . ?
C3 C7 C8 C9 -178.9(4) . . . . ?
C7 C8 C9 C10 -1.0(7) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C12 1.0(7) . . . . ?
C8 C7 C12 C11 0.5(6) . . . . ?
C3 C7 C12 C11 -179.9(4) . . . . ?
C10 C11 C12 C7 -1.3(7) . . . . ?
O2 S1 C13 F5 -74.0(4) . . . . ?
N1 S1 C13 F5 38.5(4) . . . . ?
O2 S1 C13 F4 171.6(3) . . . . ?
N1 S1 C13 F4 -75.9(3) . . . . ?
O2 S1 C13 C14 58.0(4) . . . . ?
N1 S1 C13 C14 170.4(4) . . . . ?
F5 C13 C14 F7 167.8(5) . . . . ?
F4 C13 C14 F7 -75.8(7) . . . . ?
S1 C13 C14 F7 36.5(7) . . . . ?
F5 C13 C14 F6 52.8(6) . . . . ?
F4 C13 C14 F6 169.3(4) . . . . ?
S1 C13 C14 F6 -78.5(5) . . . . ?
F5 C13 C14 Cl1 -59.7(6) . . . . ?
F4 C13 C14 Cl1 56.7(5) . . . . ?
S1 C13 C14 Cl1 168.9(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190577
