#------------------------------------------------------------------------------
#$Date: 2019-11-23 23:32:55 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235603 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/70/4037050.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_4037050
loop_
_publ_author_name
'Le Guen, Clothilde'
'Tran Do, Minh-Loan'
'Chardon, Aurélien'
'Lebargy, Cyril'
'Lohier, Jean-François'
'Pfund, Emmanuel'
'Lequeux, Thierry'
_publ_section_title
;
 Access to Fluoropyrrolidines by Intramolecular Aza-Michael Addition
 Reaction.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6714
_journal_page_last               6720
_journal_paper_doi               10.1021/acs.joc.6b01363
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C19 H19 F N2 O2 S2'
_chemical_formula_sum            'C19 H19 F N2 O2 S2'
_chemical_formula_weight         390.48
_chemical_melting_point          355
_chemical_name_systematic
2-[(Fluoro-2-benzothiazolylsulfonyl)-ethyl]-1-benzylpyrrolidine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.3530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6636(3)
_cell_length_b                   15.0363(3)
_cell_length_c                   10.1827(2)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      32.11
_cell_measurement_theta_min      2.49
_cell_volume                     1860.49(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40928
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.242
_diffrn_reflns_theta_min         2.486
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         7119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0645P)²+0.4271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5193
_reflns_number_total             7119
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b01363_si_001.cif
_cod_data_source_block           leguen1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037050
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.78329(3) 0.16427(3) 0.56506(4) 0.04786(11) Uani 1 1 d . .
S2 S 0.95959(3) 0.13424(2) 0.83449(5) 0.05465(12) Uani 1 1 d . .
F1 F 0.64740(8) 0.18757(9) 0.70642(10) 0.0652(3) Uani 1 1 d . .
N1 N 0.47414(8) 0.26578(7) 0.47573(12) 0.0379(2) Uani 1 1 d . .
N2 N 0.91776(9) 0.28734(8) 0.71395(13) 0.0431(2) Uani 1 1 d . .
O2 O 0.77566(11) 0.07091(8) 0.58786(18) 0.0789(4) Uani 1 1 d . .
O1 O 0.79771(10) 0.19662(12) 0.43994(14) 0.0766(4) Uani 1 1 d . .
C14 C 0.99878(10) 0.30166(9) 0.83514(15) 0.0420(3) Uani 1 1 d . .
C2 C 0.56380(10) 0.20591(8) 0.46661(14) 0.0383(2) Uani 1 1 d . .
H2 H 0.5834 0.2180 0.3818 0.046 Uiso 1 1 calc R U
C7 C 0.39272(11) 0.41623(8) 0.43263(15) 0.0408(3) Uani 1 1 d . .
C1 C 0.66342(10) 0.22067(8) 0.58807(15) 0.0397(3) Uani 1 1 d . .
H1 H 0.6786 0.2846 0.5990 0.048 Uiso 1 1 calc R U
C13 C 0.89124(10) 0.20434(9) 0.70395(15) 0.0421(3) Uani 1 1 d . .
C15 C 1.03257(11) 0.22534(9) 0.91566(16) 0.0449(3) Uani 1 1 d . .
C12 C 0.33883(13) 0.47078(9) 0.32523(16) 0.0466(3) Uani 1 1 d . .
H12 H 0.3567 0.4677 0.2428 0.056 Uiso 1 1 calc R U
C8 C 0.36500(15) 0.42286(11) 0.55418(18) 0.0559(4) Uani 1 1 d . .
H8 H 0.4005 0.3870 0.6278 0.067 Uiso 1 1 calc R U
C6 C 0.48154(12) 0.35369(9) 0.41705(19) 0.0496(3) Uani 1 1 d . .
H6A H 0.4760 0.3471 0.3206 0.059 Uiso 1 1 calc R U
H6B H 0.5529 0.3794 0.4616 0.059 Uiso 1 1 calc R U
C11 C 0.25817(14) 0.53026(10) 0.33872(18) 0.0544(4) Uani 1 1 d . .
H11 H 0.2227 0.5665 0.2656 0.065 Uiso 1 1 calc R U
C5 C 0.37261(12) 0.21888(9) 0.40634(18) 0.0487(3) Uani 1 1 d . .
H5A H 0.3578 0.2225 0.3077 0.058 Uiso 1 1 calc R U
H5B H 0.3103 0.2429 0.4324 0.058 Uiso 1 1 calc R U
C19 C 1.04371(14) 0.38449(11) 0.88303(19) 0.0558(4) Uani 1 1 d . .
H19 H 1.0234 0.4353 0.8298 0.067 Uiso 1 1 calc R U
C16 C 1.10960(13) 0.23125(12) 1.04434(19) 0.0581(4) Uani 1 1 d . .
H16 H 1.1326 0.1808 1.0974 0.070 Uiso 1 1 calc R U
C10 C 0.23104(14) 0.53542(10) 0.4595(2) 0.0573(4) Uani 1 1 d . .
H10 H 0.1766 0.5745 0.4684 0.069 Uiso 1 1 calc R U
C3 C 0.51531(13) 0.11143(10) 0.4607(2) 0.0575(4) Uani 1 1 d . .
H3A H 0.5215 0.0802 0.3799 0.069 Uiso 1 1 calc R U
H3B H 0.5534 0.0775 0.5411 0.069 Uiso 1 1 calc R U
C9 C 0.28509(17) 0.48225(12) 0.5678(2) 0.0630(4) Uani 1 1 d . .
H9 H 0.2678 0.4862 0.6506 0.076 Uiso 1 1 calc R U
C18 C 1.11806(15) 0.38938(13) 1.0097(2) 0.0639(4) Uani 1 1 d . .
H18 H 1.1478 0.4443 1.0429 0.077 Uiso 1 1 calc R U
C4 C 0.39630(14) 0.12447(10) 0.4556(2) 0.0588(4) Uani 1 1 d . .
H4A H 0.3854 0.1168 0.5455 0.071 Uiso 1 1 calc R U
H4B H 0.3494 0.0829 0.3925 0.071 Uiso 1 1 calc R U
C17 C 1.15012(14) 0.31358(14) 1.0899(2) 0.0635(4) Uani 1 1 d . .
H17 H 1.2001 0.3190 1.1761 0.076 Uiso 1 1 calc R U
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'
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
O1 S1 O2 120.83(10)
O1 S1 C13 109.49(7)
O2 S1 C13 106.04(8)
O1 S1 C1 106.22(8)
O2 S1 C1 109.95(7)
C13 S1 C1 102.93(6)
C13 S2 C15 88.22(7)
C5 N1 C6 112.75(12)
C5 N1 C2 105.27(10)
C6 N1 C2 112.77(10)
C13 N2 C14 109.45(12)
N2 C14 C19 125.25(13)
N2 C14 C15 114.92(13)
C19 C14 C15 119.78(14)
N1 C2 C1 109.81(10)
N1 C2 C3 105.07(11)
C1 C2 C3 113.44(11)
N1 C2 H2 109.5
C1 C2 H2 109.5
C3 C2 H2 109.5
C8 C7 C12 118.17(13)
C8 C7 C6 121.61(13)
C12 C7 C6 120.19(13)
F1 C1 C2 111.69(10)
F1 C1 S1 106.30(9)
C2 C1 S1 111.21(9)
F1 C1 H1 109.2
C2 C1 H1 109.2
S1 C1 H1 109.2
N2 C13 S2 117.87(11)
N2 C13 S1 121.15(11)
S2 C13 S1 120.90(8)
C16 C15 C14 120.81(15)
C16 C15 S2 129.54(12)
C14 C15 S2 109.54(11)
C7 C12 C11 120.98(14)
C7 C12 H12 119.5
C11 C12 H12 119.5
C7 C8 C9 120.88(15)
C7 C8 H8 119.6
C9 C8 H8 119.6
N1 C6 C7 112.61(11)
N1 C6 H6A 109.1
C7 C6 H6A 109.1
N1 C6 H6B 109.1
C7 C6 H6B 109.1
H6A C6 H6B 107.8
C10 C11 C12 120.08(15)
C10 C11 H11 120.0
C12 C11 H11 120.0
N1 C5 C4 103.17(12)
N1 C5 H5A 111.1
C4 C5 H5A 111.1
N1 C5 H5B 111.1
C4 C5 H5B 111.1
H5A C5 H5B 109.1
C18 C19 C14 118.75(16)
C18 C19 H19 120.6
C14 C19 H19 120.6
C17 C16 C15 118.06(16)
C17 C16 H16 121.0
C15 C16 H16 121.0
C11 C10 C9 119.50(15)
C11 C10 H10 120.2
C9 C10 H10 120.2
C4 C3 C2 105.36(11)
C4 C3 H3A 110.7
C2 C3 H3A 110.7
C4 C3 H3B 110.7
C2 C3 H3B 110.7
H3A C3 H3B 108.8
C10 C9 C8 120.38(16)
C10 C9 H9 119.8
C8 C9 H9 119.8
C19 C18 C17 121.19(17)
C19 C18 H18 119.4
C17 C18 H18 119.4
C3 C4 C5 103.74(13)
C3 C4 H4A 111.0
C5 C4 H4A 111.0
C3 C4 H4B 111.0
C5 C4 H4B 111.0
H4A C4 H4B 109.0
C16 C17 C18 121.38(17)
C16 C17 H17 119.3
C18 C17 H17 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4228(14)
S1 O2 1.4305(14)
S1 C13 1.7729(15)
S1 C1 1.8107(12)
S2 C13 1.7260(14)
S2 C15 1.7273(16)
F1 C1 1.3707(17)
N1 C5 1.4622(18)
N1 C6 1.4645(17)
N1 C2 1.4722(15)
N2 C13 1.2889(17)
N2 C14 1.3817(19)
C14 C19 1.399(2)
C14 C15 1.4052(19)
C2 C1 1.5139(19)
C2 C3 1.5422(19)
C2 H2 0.9800
C7 C8 1.382(2)
C7 C12 1.384(2)
C7 C6 1.5084(18)
C1 H1 0.9800
C15 C16 1.399(2)
C12 C11 1.393(2)
C12 H12 0.9300
C8 C9 1.386(2)
C8 H8 0.9300
C6 H6A 0.9700
C6 H6B 0.9700
C11 C10 1.369(3)
C11 H11 0.9300
C5 C4 1.507(2)
C5 H5A 0.9700
C5 H5B 0.9700
C19 C18 1.368(3)
C19 H19 0.9300
C16 C17 1.370(3)
C16 H16 0.9300
C10 C9 1.378(3)
C10 H10 0.9300
C3 C4 1.506(2)
C3 H3A 0.9700
C3 H3B 0.9700
C9 H9 0.9300
C18 C17 1.394(3)
C18 H18 0.9300
C4 H4A 0.9700
C4 H4B 0.9700
C17 H17 0.9300
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
C2 H2 F1 0.98 2.58 3.5050(16) 156.5 4_565
C2 H2 F1 0.98 2.58 3.5050(16) 156.5 4_565
