#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023821.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_4023821
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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H22 N2 O4 S1'
_chemical_formula_sum            'C23 H22 N2 O4 S'
_chemical_formula_weight         422.49
_chemical_name_systematic
;
 3-Benzenesulfonyl-7-methyl-1-phenyl-2a,3,4,4a,5,7b-
hexahydro-1H-1,3-diaza-cyclobut[e]indene-2,6-dione 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-04-30T15:47:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                97.111(2)
_cell_angle_beta                 92.414(1)
_cell_angle_gamma                112.811(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0604(3)
_cell_length_b                   8.3944(3)
_cell_length_c                   16.6281(8)
_cell_measurement_reflns_used    14021
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      1.24
_cell_measurement_wavelength     0.71073
_cell_volume                     1024.12(7)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_unetI/netI     0.046
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4822
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1296P)²+0.0562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.2121
_reflns_number_gt                3409
_reflns_number_total             4822
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801668b_si_001_1.cif
_cod_data_source_block           compound_13b
_cod_database_code               4023821
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
C1 C 0.4413(3) 0.0468(3) 0.85824(14) 0.0403(5) Uani 1 1 d . . .
H1 H 0.3563 0.0736 0.8923 0.048 Uiso 1 1 calc R . .
C2 C 0.5909(3) 0.2159(3) 0.83462(13) 0.0370(5) Uani 1 1 d . . .
H2 H 0.5717 0.3236 0.8499 0.044 Uiso 1 1 calc R . .
C3 C 0.6245(3) 0.1836(3) 0.74804(13) 0.0401(5) Uani 1 1 d . . .
C4 C 0.6393(3) 0.2828(3) 0.68968(16) 0.0534(7) Uani 1 1 d . . .
C5 C 0.6593(4) 0.1863(5) 0.61268(17) 0.0750(10) Uani 1 1 d . . .
C6 C 0.6537(4) 0.0127(5) 0.62783(18) 0.0781(10) Uani 1 1 d . . .
H6A H 0.7641 0 0.6141 0.094 Uiso 1 1 calc R . .
H6B H 0.5518 -0.0814 0.5956 0.094 Uiso 1 1 calc R . .
C7 C 0.6338(3) 0.0098(3) 0.71905(15) 0.0485(6) Uani 1 1 d . . .
H7 H 0.7446 0.0089 0.7453 0.058 Uiso 1 1 calc R . .
C8 C 0.4712(4) -0.1457(3) 0.74038(18) 0.0557(7) Uani 1 1 d . . .
H8A H 0.4009 -0.2152 0.6902 0.067 Uiso 1 1 calc R . .
H8B H 0.5162 -0.2189 0.7676 0.067 Uiso 1 1 calc R . .
C9 C 0.6369(4) 0.4617(4) 0.6953(2) 0.0781(11) Uani 1 1 d . . .
H9A H 0.5348 0.4562 0.6615 0.117 Uiso 1 1 calc R . .
H9B H 0.7464 0.5402 0.6774 0.117 Uiso 1 1 calc R . .
H9C H 0.6281 0.5031 0.7508 0.117 Uiso 1 1 calc R . .
C10 C 0.5960(3) 0.0306(3) 0.90884(15) 0.0446(5) Uani 1 1 d . . .
C11 C 0.9045(3) 0.2819(3) 0.91180(12) 0.0372(5) Uani 1 1 d . . .
C12 C 1.0048(3) 0.2197(3) 0.95936(15) 0.0486(6) Uani 1 1 d . . .
H12 H 0.9486 0.1147 0.9791 0.058 Uiso 1 1 calc R . .
C13 C 1.1880(4) 0.3147(4) 0.97708(17) 0.0574(7) Uani 1 1 d . . .
H13 H 1.2554 0.2729 1.0087 0.069 Uiso 1 1 calc R . .
C14 C 1.2729(4) 0.4708(3) 0.94856(18) 0.0573(7) Uani 1 1 d . . .
H14 H 1.3968 0.5337 0.9606 0.069 Uiso 1 1 calc R . .
C15 C 1.1725(3) 0.5332(3) 0.90198(17) 0.0525(6) Uani 1 1 d . . .
H15 H 1.2291 0.6392 0.8831 0.063 Uiso 1 1 calc R . .
C16 C 0.9893(3) 0.4396(3) 0.88317(14) 0.0435(5) Uani 1 1 d . . .
H16 H 0.9226 0.4819 0.8514 0.052 Uiso 1 1 calc R . .
C17 C 0.1481(3) 0.0219(3) 0.69826(14) 0.0408(5) Uani 1 1 d . . .
C18 C 0.1329(3) 0.1733(3) 0.73370(14) 0.0435(5) Uani 1 1 d . . .
H18 H 0.1189 0.1902 0.7889 0.052 Uiso 1 1 calc R . .
C19 C 0.1390(3) 0.2994(3) 0.68609(16) 0.0500(6) Uani 1 1 d . . .
H19 H 0.1258 0.3998 0.7095 0.06 Uiso 1 1 calc R . .
C20 C 0.1642(3) 0.2786(3) 0.60446(15) 0.0515(6) Uani 1 1 d . . .
C21 C 0.1816(4) 0.1278(4) 0.57113(16) 0.0595(7) Uani 1 1 d . . .
H21 H 0.1999 0.1129 0.5163 0.071 Uiso 1 1 calc R . .
C22 C 0.1726(4) -0.0021(3) 0.61652(16) 0.0552(6) Uani 1 1 d . . .
H22 H 0.1829 -0.1036 0.5926 0.066 Uiso 1 1 calc R . .
C23 C 0.1730(5) 0.4170(5) 0.5529(2) 0.0828(10) Uani 1 1 d . . .
H23A H 0.297 0.4851 0.5459 0.124 Uiso 1 1 calc R . .
H23B H 0.1205 0.4919 0.5794 0.124 Uiso 1 1 calc R . .
H23C H 0.1072 0.3621 0.5006 0.124 Uiso 1 1 calc R . .
N1 N 0.7175(2) 0.1876(2) 0.89257(11) 0.0395(4) Uani 1 1 d . . .
N2 N 0.3508(2) -0.0953(2) 0.79290(12) 0.0429(5) Uani 1 1 d . . .
O1 O 0.6115(3) -0.0782(2) 0.94613(12) 0.0612(5) Uani 1 1 d . . .
O2 O 0.6766(4) 0.2363(5) 0.54692(14) 0.1194(12) Uani 1 1 d . . .
O3 O 0.0829(3) -0.3019(2) 0.70639(15) 0.0722(6) Uani 1 1 d . . .
O4 O 0.0494(2) -0.1183(3) 0.82766(13) 0.0626(5) Uani 1 1 d . . .
S1 S 0.14253(8) -0.13796(7) 0.75861(4) 0.0486(2) 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 0 '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 0.006 '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
N2 C1 C10 115.00(18) . . ?
N2 C1 C2 116.52(18) . . ?
C10 C1 C2 85.69(16) . . ?
N1 C2 C3 113.41(17) . . ?
N1 C2 C1 86.34(15) . . ?
C3 C2 C1 110.05(18) . . ?
C4 C3 C2 129.5(2) . . ?
C4 C3 C7 113.9(2) . . ?
C2 C3 C7 116.56(18) . . ?
C3 C4 C5 108.3(3) . . ?
C3 C4 C9 129.1(3) . . ?
C5 C4 C9 122.6(2) . . ?
O2 C5 C4 126.7(4) . . ?
O2 C5 C6 124.3(4) . . ?
C4 C5 C6 109.0(2) . . ?
C5 C6 C7 105.5(2) . . ?
C3 C7 C6 103.3(2) . . ?
C3 C7 C8 112.49(19) . . ?
C6 C7 C8 115.5(2) . . ?
N2 C8 C7 114.38(19) . . ?
O1 C10 N1 132.7(2) . . ?
O1 C10 C1 135.4(2) . . ?
N1 C10 C1 91.80(16) . . ?
C16 C11 C12 119.8(2) . . ?
C16 C11 N1 119.42(19) . . ?
C12 C11 N1 120.8(2) . . ?
C13 C12 C11 119.5(2) . . ?
C14 C13 C12 120.9(2) . . ?
C13 C14 C15 119.5(2) . . ?
C16 C15 C14 120.5(2) . . ?
C15 C16 C11 119.8(2) . . ?
C22 C17 C18 120.4(2) . . ?
C22 C17 S1 119.96(18) . . ?
C18 C17 S1 119.57(18) . . ?
C17 C18 C19 119.4(2) . . ?
C20 C19 C18 121.2(2) . . ?
C21 C20 C19 118.2(2) . . ?
C21 C20 C23 120.7(3) . . ?
C19 C20 C23 121.1(3) . . ?
C20 C21 C22 122.1(2) . . ?
C21 C22 C17 118.7(2) . . ?
C10 N1 C11 134.12(18) . . ?
C10 N1 C2 95.65(17) . . ?
C11 N1 C2 129.58(17) . . ?
C1 N2 C8 115.23(19) . . ?
C1 N2 S1 119.68(15) . . ?
C8 N2 S1 120.55(18) . . ?
O4 S1 O3 120.23(13) . . ?
O4 S1 N2 106.84(12) . . ?
O3 S1 N2 105.52(11) . . ?
O4 S1 C17 108.16(11) . . ?
O3 S1 C17 107.80(13) . . ?
N2 S1 C17 107.72(10) . . ?
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
C1 N2 1.440(3) . ?
C1 C10 1.534(3) . ?
C1 C2 1.573(3) . ?
C2 N1 1.479(3) . ?
C2 C3 1.487(3) . ?
C3 C4 1.335(3) . ?
C3 C7 1.511(3) . ?
C4 C5 1.478(4) . ?
C4 C9 1.500(4) . ?
C5 O2 1.214(4) . ?
C5 C6 1.494(5) . ?
C6 C7 1.534(4) . ?
C7 C8 1.540(3) . ?
C8 N2 1.477(3) . ?
C10 O1 1.207(3) . ?
C10 N1 1.371(3) . ?
C11 C16 1.388(3) . ?
C11 C12 1.388(3) . ?
C11 N1 1.405(3) . ?
C12 C13 1.377(4) . ?
C13 C14 1.377(4) . ?
C14 C15 1.380(3) . ?
C15 C16 1.377(3) . ?
C17 C22 1.383(3) . ?
C17 C18 1.385(3) . ?
C17 S1 1.760(2) . ?
C18 C19 1.386(3) . ?
C19 C20 1.381(4) . ?
C20 C21 1.379(4) . ?
C20 C23 1.509(4) . ?
C21 C22 1.382(4) . ?
N2 S1 1.6353(19) . ?
O3 S1 1.426(2) . ?
O4 S1 1.425(2) . ?
