#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023822.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_4023822
loop_
_publ_author_name
'Clarisse Olier'
'Nadia Azzi'
'Gérard Gil'
'Stéphane Gastaldi'
'Michèle P. Bertrand'
_publ_contact_author_address
;
   Laboratoire de Chimie Moleculaire Organique
   UMR 6264 LCP boite 562
   Universite Paul Cezanne
   Faculte des Sciences St Jerome
   Avenue Escadrille Normandie Niemen
   13397 Marseille Cedex 20 France. 
;
_publ_contact_author_email       michele.bertrand@univ-cezanne.fr
_publ_contact_author_name        'Michele, P., Bertrand'
_publ_section_title
;
 Dicobalt Hexacarbonyl Complexes of Alkynyl Imines in
 a Sequential Staudinger/Pauson-Khand Process.
 A Route to New Fused Tricyclic β-Lactams
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8469
_journal_page_last               8473
_journal_paper_doi               10.1021/jo801668b
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C24 H25 Cl3 N2 O4 S'
_chemical_formula_weight         543.87
_chemical_name_systematic
; 
 Benzenesulfonyl-5-methyl-6-oxo-2,3,4,6,7,7a-
hexahydro-1H-2-pyrindine-3-carboxylic acid phenylamide  
;
_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                 116.5581(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8864(1)
_cell_length_b                   16.4396(2)
_cell_length_c                   19.6870(3)
_cell_measurement_reflns_used    18389
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      1.16
_cell_volume                     2572.57(6)
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Bruker-Nonius, 1998)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Phi scan'
_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  0.036
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18389
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1342P)²+1.4584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2185
_reflns_number_gt                3946
_reflns_number_total             4750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801668b_si_001_2.cif
_cod_data_source_block           compound_14b
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023822
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
Cl1 Cl 0.3251(3) -0.20221(11) 0.13140(15) 0.1520(8) Uani 1 1 d . . .
Cl2 Cl 0.3323(4) -0.03473(13) 0.10881(14) 0.1771(10) Uani 1 1 d . . .
Cl3 Cl 0.6146(3) -0.11528(16) 0.23274(14) 0.1614(9) Uani 1 1 d . . .
S1 S 0.30647(8) 0.12742(4) 0.47509(4) 0.0382(2) Uani 1 1 d . . .
O1 O 0.4475(3) 0.12065(13) 0.54796(11) 0.0493(5) Uani 1 1 d . . .
O2 O 0.1475(3) 0.09264(13) 0.46212(13) 0.0488(5) Uani 1 1 d . . .
O3 O 0.8185(3) 0.10921(19) 0.27482(15) 0.0718(8) Uani 1 1 d . . .
O4 O 0.2170(3) -0.05777(15) 0.27313(12) 0.0574(6) Uani 1 1 d . . .
N1 N 0.1350(3) -0.05553(14) 0.36738(14) 0.0420(5) Uani 1 1 d . . .
N2 N 0.3598(3) 0.08340(13) 0.41489(12) 0.0358(5) Uani 1 1 d . . .
H1 H 0.1264 -0.0214 0.3995 0.053(9) Uiso 1 1 d R . .
C1 C 0.2731(4) 0.23131(17) 0.45086(15) 0.0398(6) Uani 1 1 d . . .
C2 C 0.1217(4) 0.25721(19) 0.39374(19) 0.0519(7) Uani 1 1 d . . .
H2 H 0.0352 0.2203 0.3684 0.062 Uiso 1 1 calc R . .
C3 C 0.1004(5) 0.3384(2) 0.3747(2) 0.0608(9) Uani 1 1 d . . .
H3 H -0.0013 0.3559 0.3360 0.073 Uiso 1 1 calc R . .
C4 C 0.2267(5) 0.3945(2) 0.4118(2) 0.0605(9) Uani 1 1 d . . .
C5 C 0.3759(5) 0.3670(2) 0.4681(2) 0.0639(9) Uani 1 1 d . . .
H5 H 0.4618 0.4041 0.4936 0.077 Uiso 1 1 calc R . .
C6 C 0.4027(4) 0.28622(19) 0.48829(17) 0.0516(7) Uani 1 1 d . . .
H6 H 0.5056 0.2688 0.5262 0.062 Uiso 1 1 calc R . .
C7 C 0.1987(7) 0.4837(2) 0.3900(3) 0.0933(15) Uani 1 1 d . . .
H7A H 0.2921 0.5150 0.4253 0.140 Uiso 1 1 calc R . .
H7B H 0.0971 0.5020 0.3910 0.140 Uiso 1 1 calc R . .
H7C H 0.1892 0.4906 0.3398 0.140 Uiso 1 1 calc R . .
C8 C 0.5386(3) 0.09054(18) 0.43022(15) 0.0401(6) Uani 1 1 d . . .
H8A H 0.6097 0.0633 0.4775 0.048 Uiso 1 1 calc R . .
H8B H 0.5708 0.1474 0.4351 0.048 Uiso 1 1 calc R . .
C9 C 0.5627(3) 0.05229(17) 0.36568(15) 0.0377(6) Uani 1 1 d . . .
H9 H 0.5325 -0.0055 0.3615 0.045 Uiso 1 1 calc R . .
C10 C 0.7382(4) 0.0617(2) 0.37078(17) 0.0504(7) Uani 1 1 d . . .
H10A H 0.8066 0.0975 0.4124 0.060 Uiso 1 1 calc R . .
H10B H 0.7937 0.0093 0.3786 0.060 Uiso 1 1 calc R . .
C11 C 0.7114(4) 0.0977(2) 0.29622(18) 0.0491(7) Uani 1 1 d . . .
C12 C 0.5321(4) 0.12037(19) 0.25377(17) 0.0470(7) Uani 1 1 d . . .
C13 C 0.4505(3) 0.09550(17) 0.29289(15) 0.0386(6) Uani 1 1 d . . .
C14 C 0.2735(3) 0.11093(19) 0.27759(16) 0.0439(6) Uani 1 1 d . . .
H14A H 0.1990 0.0907 0.2274 0.053 Uiso 1 1 calc R . .
H14B H 0.2558 0.1691 0.2779 0.053 Uiso 1 1 calc R . .
C15 C 0.2280(3) 0.07049(17) 0.33589(14) 0.0382(6) Uani 1 1 d . . .
H15 H 0.1243 0.0959 0.3315 0.046 Uiso 1 1 calc R . .
C16 C 0.1942(3) -0.02148(18) 0.32164(15) 0.0394(6) Uani 1 1 d . . .
C17 C 0.4665(5) 0.1662(3) 0.1806(2) 0.0725(11) Uani 1 1 d . . .
H17A H 0.3535 0.1838 0.1668 0.109 Uiso 1 1 calc R . .
H17B H 0.4673 0.1315 0.1415 0.109 Uiso 1 1 calc R . .
H17C H 0.5365 0.2127 0.1864 0.109 Uiso 1 1 calc R . .
C18 C 0.1040(3) -0.13783(16) 0.37634(15) 0.0381(6) Uani 1 1 d . . .
C19 C 0.0268(4) -0.15419(18) 0.42250(17) 0.0461(7) Uani 1 1 d . . .
H19 H -0.0061 -0.1115 0.4439 0.055 Uiso 1 1 calc R . .
C20 C -0.0012(5) -0.2335(2) 0.4368(2) 0.0584(8) Uani 1 1 d . . .
H20 H -0.0526 -0.2440 0.4680 0.070 Uiso 1 1 calc R . .
C21 C 0.0468(5) -0.2972(2) 0.4051(2) 0.0583(8) Uani 1 1 d . . .
H21 H 0.0286 -0.3506 0.4151 0.070 Uiso 1 1 calc R . .
C22 C 0.1212(4) -0.2813(2) 0.35890(19) 0.0552(8) Uani 1 1 d . . .
H22 H 0.1523 -0.3242 0.3371 0.066 Uiso 1 1 calc R . .
C23 C 0.1507(4) -0.20228(19) 0.34429(18) 0.0491(7) Uani 1 1 d . . .
H23 H 0.2019 -0.1922 0.3130 0.059 Uiso 1 1 calc R . .
C24 C 0.3976(9) -0.1114(3) 0.1776(4) 0.1091(19) Uani 1 1 d . . .
H24 H 0.3448 -0.1020 0.2113 0.131 Uiso 1 1 calc R . .
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'
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'
O O 0.0106 0.0060 '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'
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
O1 S1 O2 119.97(13) . . ?
O1 S1 N2 106.65(12) . . ?
O2 S1 N2 106.07(12) . . ?
O1 S1 C1 108.29(13) . . ?
O2 S1 C1 107.72(13) . . ?
N2 S1 C1 107.57(12) . . ?
C16 N1 C18 129.7(2) . . ?
C16 N1 H1 113.7 . . ?
C18 N1 H1 116.1 . . ?
C8 N2 C15 119.7(2) . . ?
C8 N2 S1 116.77(17) . . ?
C15 N2 S1 118.37(17) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 S1 120.3(2) . . ?
C6 C1 S1 119.2(2) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C7 121.7(3) . . ?
C3 C4 C7 120.3(3) . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 109.6(2) . . ?
N2 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N2 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C13 C9 C8 108.7(2) . . ?
C13 C9 C10 103.7(2) . . ?
C8 C9 C10 115.2(2) . . ?
C13 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
C11 C10 C9 105.4(2) . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
O3 C11 C12 125.3(3) . . ?
O3 C11 C10 126.5(3) . . ?
C12 C11 C10 108.2(2) . . ?
C13 C12 C11 108.8(3) . . ?
C13 C12 C17 129.2(3) . . ?
C11 C12 C17 122.0(3) . . ?
C12 C13 C14 129.0(3) . . ?
C12 C13 C9 113.1(2) . . ?
C14 C13 C9 117.6(2) . . ?
C13 C14 C15 112.6(2) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N2 C15 C14 112.0(2) . . ?
N2 C15 C16 109.2(2) . . ?
C14 C15 C16 112.6(2) . . ?
N2 C15 H15 107.6 . . ?
C14 C15 H15 107.6 . . ?
C16 C15 H15 107.6 . . ?
O4 C16 N1 124.8(3) . . ?
O4 C16 C15 122.4(2) . . ?
N1 C16 C15 112.8(2) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 119.0(3) . . ?
C19 C18 N1 116.8(2) . . ?
C23 C18 N1 124.1(3) . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 120.0(3) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
Cl1 C24 Cl3 110.3(3) . . ?
Cl1 C24 Cl2 107.5(4) . . ?
Cl3 C24 Cl2 113.6(3) . . ?
Cl1 C24 H24 108.4 . . ?
Cl3 C24 H24 108.4 . . ?
Cl2 C24 H24 108.4 . . ?
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
Cl1 C24 1.717(6) . ?
Cl2 C24 1.749(7) . ?
Cl3 C24 1.740(7) . ?
S1 O1 1.426(2) . ?
S1 O2 1.437(2) . ?
S1 N2 1.630(2) . ?
S1 C1 1.762(3) . ?
O3 C11 1.216(4) . ?
O4 C16 1.217(3) . ?
N1 C16 1.351(3) . ?
N1 C18 1.408(4) . ?
N1 H1 0.8742 . ?
N2 C8 1.483(3) . ?
N2 C15 1.485(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.388(4) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 C7 1.517(5) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.516(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.508(3) . ?
C9 C10 1.526(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.500(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.478(4) . ?
C12 C13 1.337(4) . ?
C12 C17 1.494(4) . ?
C13 C14 1.485(4) . ?
C14 C15 1.529(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.543(4) . ?
C15 H15 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.387(4) . ?
C18 C23 1.388(4) . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 0.9800 . ?
