#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:58:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178675 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/86/4078614.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_4078614
loop_
_publ_author_name
'Lu, Bei-Li'
'Wei, Yin'
'Shi, Min'
_publ_section_title
;
 Rhodium(I)-Catalyzed Pauson--Khand-type [3 + 2 + 1] Cycloaddition
 Reaction of Ene-Vinylidenecyclopropanes and CO: A Highly Regio- and
 Stereoselective Synthetic Approach for the Preparation of Aza- and
 Oxa-Bicyclic Compounds
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              4601
_journal_paper_doi               10.1021/om3004288
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C21 H27 N O3 S'
_chemical_formula_weight         373.50
_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                91.113(2)
_cell_angle_beta                 98.047(2)
_cell_angle_gamma                95.389(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5624(12)
_cell_length_b                   8.6068(12)
_cell_length_c                   13.3479(19)
_cell_measurement_reflns_used    3389
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.38
_cell_volume                     969.2(2)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7668
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_correction_T_min  0.9460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1019P)²+0.2342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                3865
_reflns_number_total             4611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om3004288_si_002.cif
_cod_data_source_block           mo_dm11276_0m
_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_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4078614
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
S1 S 0.29512(5) 0.17801(5) 0.49094(3) 0.01704(15) Uani 1 1 d .
N1 N 0.40084(18) 0.09856(18) 0.58454(11) 0.0180(3) Uani 1 1 d .
O1 O 0.34065(18) 0.1910(2) 0.95585(12) 0.0339(4) Uani 1 1 d .
O2 O 0.40439(16) 0.24621(17) 0.42789(10) 0.0224(3) Uani 1 1 d .
O3 O 0.17146(16) 0.06127(16) 0.44940(10) 0.0229(3) Uani 1 1 d .
C1 C 0.5540(2) 0.1816(2) 0.63008(14) 0.0197(4) Uani 1 1 d .
H1A H 0.5413 0.2906 0.6499 0.024 Uiso 1 1 calc R
H1B H 0.6329 0.1823 0.5824 0.024 Uiso 1 1 calc R
C2 C 0.3183(2) 0.0424(2) 0.66859(14) 0.0196(4) Uani 1 1 d .
H2A H 0.2343 -0.0428 0.6453 0.024 Uiso 1 1 calc R
H2B H 0.2706 0.1281 0.7001 0.024 Uiso 1 1 calc R
C3 C 0.4513(2) -0.0169(2) 0.74223(14) 0.0214(4) Uani 1 1 d .
H3 H 0.4621 -0.1279 0.7232 0.026 Uiso 1 1 calc R
C4 C 0.6043(2) 0.0860(2) 0.72389(14) 0.0200(4) Uani 1 1 d .
H4 H 0.6856 0.0166 0.7081 0.024 Uiso 1 1 calc R
C5 C 0.6720(2) 0.1894(2) 0.81592(14) 0.0201(4) Uani 1 1 d .
C6 C 0.5451(2) 0.2713(2) 0.85641(13) 0.0196(4) Uani 1 1 d .
C7 C 0.4251(2) 0.1578(3) 0.89346(14) 0.0240(4) Uani 1 1 d .
C8 C 0.4205(3) -0.0085(3) 0.85226(15) 0.0281(4) Uani 1 1 d .
H8A H 0.3153 -0.0640 0.8571 0.034 Uiso 1 1 calc R
H8B H 0.5012 -0.0629 0.8948 0.034 Uiso 1 1 calc R
C9 C 0.8220(2) 0.1944(3) 0.86145(15) 0.0251(4) Uani 1 1 d .
C10 C 0.9468(3) 0.1059(3) 0.82340(18) 0.0361(6) Uani 1 1 d .
H10A H 0.9701 0.0194 0.8681 0.054 Uiso 1 1 calc R
H10B H 1.0436 0.1762 0.8228 0.054 Uiso 1 1 calc R
H10C H 0.9081 0.0644 0.7546 0.054 Uiso 1 1 calc R
C11 C 0.8830(3) 0.2908(3) 0.95754(18) 0.0381(6) Uani 1 1 d .
H11A H 0.7939 0.3323 0.9844 0.057 Uiso 1 1 calc R
H11B H 0.9579 0.3775 0.9426 0.057 Uiso 1 1 calc R
H11C H 0.9366 0.2249 1.0079 0.057 Uiso 1 1 calc R
C12 C 0.5297(2) 0.4259(2) 0.84992(14) 0.0229(4) Uani 1 1 d .
C13 C 0.6517(3) 0.5359(3) 0.81107(18) 0.0321(5) Uani 1 1 d .
H13A H 0.7375 0.4777 0.7932 0.048 Uiso 1 1 calc R
H13B H 0.6947 0.6156 0.8636 0.048 Uiso 1 1 calc R
H13C H 0.6028 0.5862 0.7510 0.048 Uiso 1 1 calc R
C14 C 0.3909(3) 0.5041(3) 0.87746(16) 0.0306(5) Uani 1 1 d .
H14A H 0.3047 0.4246 0.8865 0.046 Uiso 1 1 calc R
H14B H 0.3542 0.5728 0.8232 0.046 Uiso 1 1 calc R
H14C H 0.4233 0.5660 0.9406 0.046 Uiso 1 1 calc R
C15 C 0.2078(2) 0.3287(2) 0.54634(13) 0.0173(4) Uani 1 1 d .
C16 C 0.2905(2) 0.4755(2) 0.56330(15) 0.0208(4) Uani 1 1 d .
H16 H 0.3891 0.4976 0.5389 0.025 Uiso 1 1 calc R
C17 C 0.2283(2) 0.5897(2) 0.61609(15) 0.0217(4) Uani 1 1 d .
H17 H 0.2843 0.6906 0.6269 0.026 Uiso 1 1 calc R
C18 C 0.0845(2) 0.5587(2) 0.65370(15) 0.0209(4) Uani 1 1 d .
C19 C 0.0024(2) 0.4110(2) 0.63437(15) 0.0227(4) Uani 1 1 d .
H19 H -0.0964 0.3889 0.6583 0.027 Uiso 1 1 calc R
C20 C 0.0621(2) 0.2958(2) 0.58099(15) 0.0210(4) Uani 1 1 d .
H20 H 0.0047 0.1958 0.5682 0.025 Uiso 1 1 calc R
C21 C 0.0213(3) 0.6818(3) 0.71465(18) 0.0311(5) Uani 1 1 d .
H21A H -0.0941 0.6611 0.7097 0.047 Uiso 1 1 calc R
H21B H 0.0478 0.7849 0.6882 0.047 Uiso 1 1 calc R
H21C H 0.0690 0.6793 0.7857 0.047 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'
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
O3 S1 O2 120.01(8)
O3 S1 N1 106.71(8)
O2 S1 N1 106.75(8)
O3 S1 C15 108.12(8)
O2 S1 C15 108.60(9)
N1 S1 C15 105.79(8)
C2 N1 C1 107.08(14)
C2 N1 S1 117.04(12)
C1 N1 S1 118.81(13)
N1 C1 C4 103.59(15)
N1 C1 H1A 111.0
C4 C1 H1A 111.0
N1 C1 H1B 111.0
C4 C1 H1B 111.0
H1A C1 H1B 109.0
N1 C2 C3 102.86(14)
N1 C2 H2A 111.2
C3 C2 H2A 111.2
N1 C2 H2B 111.2
C3 C2 H2B 111.2
H2A C2 H2B 109.1
C2 C3 C8 112.66(16)
C2 C3 C4 104.71(15)
C8 C3 C4 112.92(16)
C2 C3 H3 108.8
C8 C3 H3 108.8
C4 C3 H3 108.8
C5 C4 C1 112.25(16)
C5 C4 C3 111.46(15)
C1 C4 C3 105.52(15)
C5 C4 H4 109.2
C1 C4 H4 109.2
C3 C4 H4 109.2
C9 C5 C6 124.18(17)
C9 C5 C4 124.08(17)
C6 C5 C4 111.39(15)
C12 C6 C7 123.33(17)
C12 C6 C5 124.85(18)
C7 C6 C5 111.41(17)
O1 C7 C6 124.0(2)
O1 C7 C8 121.1(2)
C6 C7 C8 114.86(17)
C7 C8 C3 113.00(17)
C7 C8 H8A 109.0
C3 C8 H8A 109.0
C7 C8 H8B 109.0
C3 C8 H8B 109.0
H8A C8 H8B 107.8
C5 C9 C10 124.05(19)
C5 C9 C11 122.78(18)
C10 C9 C11 113.18(18)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C6 C12 C13 121.76(18)
C6 C12 C14 124.8(2)
C13 C12 C14 113.40(19)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C16 C15 C20 120.60(17)
C16 C15 S1 119.63(14)
C20 C15 S1 119.52(15)
C17 C16 C15 119.47(17)
C17 C16 H16 120.3
C15 C16 H16 120.3
C16 C17 C18 121.09(18)
C16 C17 H17 119.5
C18 C17 H17 119.5
C19 C18 C17 118.34(17)
C19 C18 C21 121.05(18)
C17 C18 C21 120.61(18)
C20 C19 C18 121.38(17)
C20 C19 H19 119.3
C18 C19 H19 119.3
C19 C20 C15 119.08(18)
C19 C20 H20 120.5
C15 C20 H20 120.5
C18 C21 H21A 109.5
C18 C21 H21B 109.5
H21A C21 H21B 109.5
C18 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4326(14)
S1 O2 1.4369(14)
S1 N1 1.6373(16)
S1 C15 1.7573(18)
N1 C2 1.473(2)
N1 C1 1.478(2)
O1 C7 1.224(2)
C1 C4 1.544(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.529(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C8 1.530(3)
C3 C4 1.563(3)
C3 H3 1.0000
C4 C5 1.516(3)
C4 H4 1.0000
C5 C9 1.338(3)
C5 C6 1.504(2)
C6 C12 1.352(3)
C6 C7 1.492(3)
C7 C8 1.518(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.507(3)
C9 C11 1.515(3)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.497(3)
C12 C14 1.505(3)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 C16 1.388(3)
C15 C20 1.397(2)
C16 C17 1.387(3)
C16 H16 0.9500
C17 C18 1.399(3)
C17 H17 0.9500
C18 C19 1.394(3)
C18 C21 1.508(3)
C19 C20 1.386(3)
C19 H19 0.9500
C20 H20 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
