#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/66/1506630.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_1506630
loop_
_publ_author_name
'Shi, Weifeng'
'Zhang, Bo'
'Zhang, Jian'
'Liu, Binge'
'Zhang, Shiwei'
'Wang, Jianbo'
_publ_section_title
;
 Stereoselective intramolecular 1,3 C-H insertion in Rh(II) carbene
 reactions.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3103
_journal_page_last               3106
_journal_paper_doi               10.1021/ol051130l
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C15 H20 N2 O4 S'
_chemical_formula_weight         324.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   'hydrogen atoms are generated by HFIX'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.68(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.602(2)
_cell_length_b                   10.937(2)
_cell_length_c                   13.353(3)
_cell_measurement_reflns_used    15716
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.41
_cell_volume                     1693.6(6)
_computing_cell_refinement       'Molecular Structure Corporation (1994)'
_computing_data_collection       'Molecular Structure Corporation (1994)'
_computing_data_reduction        'Sheldrick, G. M. (1997) SHELXS97, Program'
_computing_molecular_graphics    'Interactive Molecular Graphics XP, Virsion'
_computing_publication_material  'Sheldrick, G. M. (1997) SHELXL97, Program'
_computing_structure_refinement  'Sheldrick, G. M. (1997) SHELXL97, Program'
_computing_structure_solution    'Sheldrick, G. M. (1997) SHELXS97, Program'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15716
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0087(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment
'hydrogen coordinates ride on the coordinates'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                1985
_reflns_number_total             3869
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051130lsi20050516_054056.cif
_cod_data_source_block           a
_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.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1506630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.26564(4) 0.15141(4) 0.30826(4) 0.06309(18) Uani 1 1 d .
O1 O 0.25270(12) 0.03066(11) 0.34988(10) 0.0837(4) Uani 1 1 d .
O2 O 0.37048(10) 0.21809(13) 0.32944(10) 0.0837(4) Uani 1 1 d .
O3 O 0.00985(11) 0.33385(12) 0.18994(10) 0.0781(4) Uani 1 1 d .
O4 O -0.11821(12) 0.17936(14) 0.19390(12) 0.0952(5) Uani 1 1 d .
N1 N -0.00334(14) 0.09041(18) 0.35423(12) 0.0766(5) Uani 1 1 d .
N2 N -0.0384(2) 0.0053(2) 0.38879(17) 0.1265(9) Uani 1 1 d .
C1 C 0.24088(14) 0.14265(16) 0.17790(14) 0.0549(5) Uani 1 1 d .
C2 C 0.18123(15) 0.04445(17) 0.13526(15) 0.0636(5) Uani 1 1 d .
H2 H 0.1582 -0.0204 0.1750 0.076 Uiso 1 1 calc R
C3 C 0.15651(17) 0.04381(19) 0.03384(17) 0.0712(6) Uani 1 1 d .
H3 H 0.1167 -0.0222 0.0058 0.085 Uiso 1 1 calc R
C4 C 0.18926(18) 0.1387(2) -0.02722(15) 0.0720(6) Uani 1 1 d .
C5 C 0.25077(18) 0.23492(19) 0.01704(17) 0.0743(6) Uani 1 1 d .
H5 H 0.2754 0.2988 -0.0230 0.089 Uiso 1 1 calc R
C6 C 0.27607(16) 0.23810(17) 0.11810(16) 0.0669(5) Uani 1 1 d .
H6 H 0.3165 0.3038 0.1461 0.080 Uiso 1 1 calc R
C7 C 0.1597(2) 0.1403(2) -0.13778(16) 0.1084(8) Uani 1 1 d .
H7A H 0.1182 0.0672 -0.1557 0.163 Uiso 1 1 calc R
H7B H 0.2294 0.1442 -0.1747 0.163 Uiso 1 1 calc R
H7C H 0.1128 0.2104 -0.1534 0.163 Uiso 1 1 calc R
C8 C 0.0864(2) 0.3627(2) 0.61958(15) 0.0951(7) Uani 1 1 d .
H8A H 0.0334 0.4237 0.6418 0.143 Uiso 1 1 calc R
H8B H 0.1636 0.3856 0.6395 0.143 Uiso 1 1 calc R
H8C H 0.0680 0.2853 0.6491 0.143 Uiso 1 1 calc R
C9 C 0.07730(17) 0.35223(19) 0.50659(14) 0.0732(6) Uani 1 1 d .
H9A H 0.0944 0.4310 0.4772 0.088 Uiso 1 1 calc R
H9B H -0.0012 0.3308 0.4868 0.088 Uiso 1 1 calc R
C10 C 0.15880(15) 0.25713(16) 0.46593(13) 0.0609(5) Uani 1 1 d .
H10A H 0.1435 0.1790 0.4972 0.073 Uiso 1 1 calc R
H10B H 0.2375 0.2802 0.4837 0.073 Uiso 1 1 calc R
C11 C 0.14681(13) 0.24293(15) 0.35178(12) 0.0515(4) Uani 1 1 d .
H11 H 0.1546 0.3246 0.3226 0.062 Uiso 1 1 calc R
C12 C 0.03501(14) 0.19155(16) 0.31333(13) 0.0549(5) Uani 1 1 d .
C13 C -0.03397(16) 0.23217(19) 0.22740(14) 0.0630(5) Uani 1 1 d .
C14 C -0.0425(2) 0.3817(2) 0.09771(17) 0.0961(8) Uani 1 1 d .
H14A H -0.0738 0.3148 0.0578 0.115 Uiso 1 1 calc R
H14B H 0.0158 0.4224 0.0592 0.115 Uiso 1 1 calc R
C15 C -0.1344(2) 0.4681(2) 0.11934(17) 0.1118(9) Uani 1 1 d .
H15A H -0.1675 0.4989 0.0576 0.168 Uiso 1 1 calc R
H15B H -0.1033 0.5347 0.1583 0.168 Uiso 1 1 calc R
H15C H -0.1928 0.4274 0.1563 0.168 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
O2 S1 O1 119.02(9)
O2 S1 C1 109.56(9)
O1 S1 C1 108.41(8)
O2 S1 C11 107.67(8)
O1 S1 C11 107.05(9)
C1 S1 C11 104.11(8)
C13 O3 C14 117.76(16)
N2 N1 C12 178.5(2)
C6 C1 C2 119.89(18)
C6 C1 S1 119.20(14)
C2 C1 S1 120.81(15)
C3 C2 C1 119.59(18)
C2 C3 C4 121.65(19)
C3 C4 C5 117.64(19)
C3 C4 C7 122.0(2)
C5 C4 C7 120.4(2)
C6 C5 C4 121.87(19)
C5 C6 C1 119.34(18)
C8 C9 C10 112.49(17)
C9 C10 C11 112.68(14)
C12 C11 C10 115.65(14)
C12 C11 S1 110.10(12)
C10 C11 S1 109.06(11)
N1 C12 C13 113.60(16)
N1 C12 C11 118.35(15)
C13 C12 C11 127.72(16)
O4 C13 O3 125.11(18)
O4 C13 C12 124.60(19)
O3 C13 C12 110.28(16)
O3 C14 C15 110.79(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4391(13)
S1 O1 1.4423(13)
S1 C1 1.7586(18)
S1 C11 1.8131(17)
O3 C13 1.327(2)
O3 C14 1.455(2)
O4 C13 1.210(2)
N1 N2 1.120(2)
N1 C12 1.317(2)
C1 C6 1.383(2)
C1 C2 1.390(2)
C2 C3 1.376(2)
C3 C4 1.380(3)
C4 C5 1.393(3)
C4 C7 1.506(3)
C5 C6 1.373(3)
C8 C9 1.514(3)
C9 C10 1.517(2)
C10 C11 1.534(2)
C11 C12 1.491(2)
C12 C13 1.449(2)
C14 C15 1.459(3)
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
O2 S1 C1 C6 -32.42(16)
O1 S1 C1 C6 -163.78(13)
C11 S1 C1 C6 82.50(15)
O2 S1 C1 C2 151.03(14)
O1 S1 C1 C2 19.68(17)
C11 S1 C1 C2 -94.05(15)
C6 C1 C2 C3 -0.8(3)
S1 C1 C2 C3 175.77(13)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 1.3(3)
C2 C3 C4 C7 -178.31(18)
C3 C4 C5 C6 -1.6(3)
C7 C4 C5 C6 177.99(19)
C4 C5 C6 C1 0.8(3)
C2 C1 C6 C5 0.4(3)
S1 C1 C6 C5 -176.14(14)
C8 C9 C10 C11 177.93(16)
C9 C10 C11 C12 -66.6(2)
C9 C10 C11 S1 168.71(13)
O2 S1 C11 C12 168.28(11)
O1 S1 C11 C12 -62.66(14)
C1 S1 C11 C12 52.03(14)
O2 S1 C11 C10 -63.83(14)
O1 S1 C11 C10 65.24(13)
C1 S1 C11 C10 179.92(12)
N2 N1 C12 C13 -42(9)
N2 N1 C12 C11 144(8)
C10 C11 C12 N1 -49.9(2)
S1 C11 C12 N1 74.23(19)
C10 C11 C12 C13 137.11(18)
S1 C11 C12 C13 -98.72(19)
C14 O3 C13 O4 -4.2(3)
C14 O3 C13 C12 174.61(17)
N1 C12 C13 O4 -0.9(3)
C11 C12 C13 O4 172.30(18)
N1 C12 C13 O3 -179.74(15)
C11 C12 C13 O3 -6.5(3)
C13 O3 C14 C15 90.8(2)
