#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2000498.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2000498
loop_
_publ_author_name
'Robinson, P. D.'
'Hua, D. H.'
'Wu, X.'
'Miao, S. W.'
'Meled, M.'
_publ_section_title
;
 Ethyl
 (2<i>R</i>,3<i>R</i>,<i>SR</i>)-3-(ethoxycarbonyloxy)-2-[1-(<i>p</i>-tolylsulfinyl)cyclopropyl]-1-pyrrolidinecarboxylate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2088
_journal_page_last               2090
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C20 H27 N O6 S'
_chemical_formula_sum            'C20 H27 N O6 S'
_chemical_formula_weight         409.50
_chemical_name_systematic
;
Ethyl (2R, 3R, SR)-3-(Ethoxycarbonyloxy)-2-[1-(p-tolylsulfinyl)
cyclopropyl]-1-pyrrolidinecarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.622(2)
_cell_length_b                   27.282(7)
_cell_length_c                   8.107(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296
_cell_measurement_theta_max      11.2
_cell_measurement_theta_min      8.1
_cell_volume                     2128.1(9)
_computing_cell_refinement
;
 MSC/AFC Diffractometer Control  Software
;
_computing_data_collection
;
 MSC/AFC Diffractometer Control Software
 (Molecular Structure Corporation, 1985)
;
_computing_data_reduction
;
 TEXSAN PROCESS
 (Molecular Structure Corporation, 1988)
;
_computing_molecular_graphics    'TEXSAN ORTEP (Johnson, 1965)'
_computing_publication_material  'TEXSAN FINISH'
_computing_structure_refinement  'TEXSAN LS'
_computing_structure_solution
;
MITHRIL (Gilmore, 1984) and DIRDIF (Beurskens, 1984)
;
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Rigaku AFC5S diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         x-ray_tube
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  no_equivalents_measured
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2197
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        1.1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       platy
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       0.0
_refine_ls_extinction_method     Zachariasen_type_2_Gaussian_isotropic
_refine_ls_goodness_of_fit_obs   1.58
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         1169
_refine_ls_R_factor_obs          0.056
_refine_ls_shift/esd_max         0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 4F~o~/\s^2^(F~o~^2^)'
_refine_ls_wR_factor_obs         0.053
_reflns_number_observed          1169
_reflns_number_total             2172
_reflns_observed_criterion       '[I>2\s(I)]'
_[local]_cod_data_source_file    cr1017.cif
_[local]_cod_data_source_block   default
_[local]_cod_cif_authors_sg_H-M  'P 21 21 21'
_cod_original_cell_volume        2128.1(8)
_cod_database_code               2000498
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
? ? ? ? ? ? ? ?
S(1) 0.084(2) 0.0510(10) 0.066(2) 0.0020(10) -0.011(2) 0.0100(10) S
O(1) 0.101(5) 0.054(3) 0.071(4) -0.002(4) 0.020(5) -0.010(3) O
O(2) 0.114(5) 0.048(3) 0.076(4) -0.025(4) 0.005(5) 0.001(3) O
O(3) 0.104(5) 0.048(3) 0.096(4) 0.012(3) -0.012(4) -0.004(3) O
O(4) 0.062(4) 0.059(3) 0.058(4) -0.009(3) -0.009(4) -0.007(3) O
O(5) 0.080(5) 0.153(7) 0.088(5) -0.043(5) 0.009(5) 0.000(5) O
O(6) 0.071(5) 0.157(7) 0.107(6) -0.013(5) -0.031(5) 0.011(6) O
N(1) 0.055(4) 0.039(4) 0.042(4) -0.002(3) 0.000(4) -0.005(3) N
C(2) 0.046(5) 0.036(4) 0.058(5) -0.001(4) -0.003(5) -0.003(4) C
C(3) 0.070(6) 0.035(4) 0.050(5) -0.011(4) 0.000(5) -0.008(4) C
C(4) 0.063(6) 0.054(5) 0.059(6) 0.006(5) 0.008(5) -0.013(4) C
C(5) 0.058(6) 0.060(5) 0.061(5) -0.007(5) 0.010(6) -0.006(4) C
C(6) 0.067(6) 0.040(4) 0.056(5) -0.009(4) 0.001(5) 0.006(4) C
C(7) 0.084(6) 0.083(6) 0.070(6) -0.022(6) 0.000(6) 0.018(6) C
C(8) 0.092(7) 0.073(6) 0.045(5) -0.006(6) 0.013(6) 0.007(5) C
C(9) 0.060(6) 0.052(5) 0.047(6) 0.016(4) -0.011(5) 0.002(5) C
C(10) 0.077(7) 0.055(5) 0.075(7) 0.007(5) -0.008(7) -0.029(5) C
C(11) 0.052(6) 0.111(8) 0.078(7) -0.007(6) 0.002(6) -0.026(6) C
C(12) 0.065(7) 0.070(6) 0.072(6) -0.010(6) -0.017(6) -0.011(5) C
C(13) 0.059(6) 0.070(6) 0.068(7) 0.001(6) -0.006(6) -0.016(5) C
C(14) 0.053(6) 0.062(5) 0.073(6) 0.005(5) 0.003(5) -0.019(5) C
C(15) 0.087(8) 0.094(7) 0.130(10) -0.017(7) 0.001(8) -0.029(7) C
C(16) 0.067(6) 0.048(5) 0.051(6) -0.014(5) -0.006(5) -0.001(5) C
C(17) 0.200(10) 0.053(6) 0.130(10) -0.052(8) 0.050(10) -0.017(6) C
C(18) 0.21(2) 0.085(8) 0.22(2) -0.070(10) -0.010(10) 0.000(10) C
C(19) 0.077(8) 0.067(6) 0.100(10) -0.013(7) 0.000(9) -0.018(7) C
C(20) 0.090(10) 0.170(10) 0.24(2) -0.020(10) -0.050(10) 0.060(10) C
C(21) 0.100(10) 0.29(2) 0.30(2) 0.040(10) -0.01(2) 0.12(2) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
S(1) 0.1489(2) 0.93719(8) 0.0718(3) .0670(10) Uani ? ? S
O(1) 0.3395(7) 0.7922(2) 0.2042(7) .075(2) Uani ? ? O
O(2) 0.1728(7) 0.7747(2) 0.3920(7) .079(2) Uani ? ? O
O(3) 0.1107(6) 0.9766(2) 0.1903(7) .083(2) Uani ? ? O
O(4) 0.4211(6) 0.9169(2) 0.5737(7) .060(2) Uani ? ? O
O(5) 0.5869(7) 0.9582(3) 0.4400(10) .107(3) Uani ? ? O
O(6) 0.6147(7) 0.9275(3) 0.6960(10) .112(3) Uani ? ? O
N(1) 0.2417(6) 0.8513(2) 0.3627(7) .045(2) Uani ? ? N
C(2) 0.3354(8) 0.8900(2) 0.3080(10) .047(2) Uani ? ? C
C(3) 0.3228(9) 0.9285(2) 0.4450(10) .052(2) Uani ? ? C
C(4) 0.1820(10) 0.9200(3) 0.5210(10) .059(3) Uani ? ? C
C(5) 0.1592(8) 0.8649(3) 0.5070(10) .060(3) Uani ? ? C
C(6) 0.3089(9) 0.9098(3) 0.1330(10) .054(2) Uani ? ? C
C(7) 0.4300(10) 0.9365(3) 0.0560(10) .079(3) Uani ? ? C
C(8) 0.3900(10) 0.8875(3) -0.0070(10) .070(3) Uani ? ? C
C(9) 0.0288(8) 0.8883(3) 0.1030(10) .053(3) Uani ? ? C
C(10) -0.0870(10) 0.8968(3) 0.1980(10) .069(3) Uani ? ? C
C(11) -0.1890(10) 0.8611(4) 0.2150(10) .080(4) Uani ? ? C
C(12) -0.1760(10) 0.8164(3) 0.1370(10) .069(3) Uani ? ? C
C(13) -0.0620(10) 0.8092(3) 0.0390(10) .066(3) Uani ? ? C
C(14) 0.0397(9) 0.8441(3) 0.0200(10) .063(3) Uani ? ? C
C(15) -0.2880(10) 0.7771(4) 0.1560(10) .104(2) Uani ? ? C
C(16) 0.2590(10) 0.8051(3) 0.3120(10) .055(3) Uani ? ? C
C(17) 0.175(2) 0.7234(3) 0.3450(10) .128(4) Uani ? ? C
C(18) 0.042(2) 0.7037(4) 0.378(2) .172(8) Uani ? ? C
C(19) 0.5460(10) 0.9365(4) 0.558(2) .081(4) Uani ? ? C
C(20) 0.7530(10) 0.9547(5) 0.710(2) .167(7) Uani ? ? C
C(21) 0.8410(10) 0.9240(8) 0.741(3) .230(8) Uani ? ? C
H(2) 0.4273 0.8774 0.3105 0.056 Uiso calc C(2) H
H(3) 0.3335 0.9610 0.4053 0.062 Uiso calc C(3) H
H(4A) 0.1123 0.9374 0.4628 0.070 Uiso calc C(4) H
H(4B) 0.1815 0.9300 0.6338 0.070 Uiso calc C(4) H
H(5A) 0.0637 0.8575 0.4906 0.072 Uiso calc C(5) H
H(5B) 0.1916 0.8484 0.6030 0.072 Uiso calc C(5) H
H(7A) 0.5099 0.9464 0.1252 0.092 Uiso d ? H
H(7B) 0.4058 0.9669 -0.0402 0.092 Uiso d ? H
H(8A) 0.3305 0.8956 -0.1256 0.086 Uiso d ? H
H(8B) 0.4279 0.8497 0.0266 0.086 Uiso d ? H
H(10) -0.0980 0.9274 0.2517 0.083 Uiso calc C(10) H
H(11) -0.2682 0.8676 0.2811 0.096 Uiso calc C(11) H
H(13) -0.0526 0.7789 -0.0178 0.079 Uiso calc C(13) H
H(14) 0.1168 0.8381 -0.0507 0.075 Uiso calc C(14) H
H(15A) -0.2750 0.7601 0.2566 0.122 Uiso calc C(15) H
H(15B) -0.2824 0.7547 0.0663 0.122 Uiso calc C(15) H
H(15C) -0.3771 0.7923 0.1557 0.122 Uiso calc C(15) H
H(17A) 0.1960 0.7204 0.2308 0.151 Uiso calc C(17) H
H(17B) 0.2433 0.7064 0.4075 0.151 Uiso calc C(17) H
H(18A) -0.0150 0.7281 0.4273 0.206 Uiso calc C(18) H
H(18B) 0.0001 0.6933 0.2772 0.206 Uiso calc C(18) H
H(18C) 0.0500 0.6765 0.4502 0.206 Uiso calc C(18) H
H(20A) 0.7741 0.9708 0.6093 0.197 Uiso calc C(20) H
H(20B) 0.7484 0.9782 0.7966 0.197 Uiso calc C(20) H
H(21A) 0.9309 0.9380 0.7265 0.274 Uiso calc C(21) H
H(21B) 0.8311 0.9133 0.8518 0.274 Uiso calc C(21) H
H(21C) 0.8306 0.8969 0.6686 0.274 Uiso calc C(21) H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .002 .002 International_Tables_Vol_IV_Table_2.3.1
H 0 0 International_Tables_Vol_IV_Table_2.3.1
O .008 .006 International_Tables_Vol_IV_Table_2.3.1
N .004 .003 International_Tables_Vol_IV_Table_2.3.1
S .110 .124 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -2 1
-1 -4 1
1 -4 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(3) S(1) C(6) 109.6(4) yes
O(3) S(1) C(9) 106.8(4) yes
C(6) S(1) C(9) 101.9(3) yes
C(16) O(2) C(17) 117.4(7) yes
C(3) O(4) C(19) 116.0(8) yes
C(19) O(6) C(20) 114.0(10) yes
C(2) N(1) C(5) 113.4(6) yes
C(2) N(1) C(16) 120.8(7) yes
C(5) N(1) C(16) 123.5(7) yes
N(1) C(2) C(3) 102.9(6) yes
N(1) C(2) C(6) 115.7(6) yes
C(3) C(2) C(6) 114.7(6) yes
O(4) C(3) C(2) 108.9(6) yes
O(4) C(3) C(4) 105.2(6) yes
C(2) C(3) C(4) 105.3(6) yes
C(3) C(4) C(5) 104.4(6) yes
N(1) C(5) C(4) 103.4(6) yes
S(1) C(6) C(2) 123.2(6) yes
S(1) C(6) C(7) 110.4(5) yes
S(1) C(6) C(8) 114.0(6) yes
C(2) C(6) C(7) 114.9(7) yes
C(2) C(6) C(8) 117.9(7) yes
C(7) C(6) C(8) 58.8(6) yes
C(6) C(7) C(8) 60.5(5) yes
C(6) C(8) C(7) 60.6(5) yes
S(1) C(9) C(10) 118.6(6) yes
S(1) C(9) C(14) 122.2(7) yes
C(10) C(9) C(14) 118.7(8) yes
C(9) C(10) C(11) 120.8(7) yes
C(10) C(11) C(12) 120.6(9) yes
C(11) C(12) C(13) 117.8(8) yes
C(11) C(12) C(15) 121.0(10) yes
C(13) C(12) C(15) 121.6(8) yes
C(12) C(13) C(14) 122.4(8) yes
C(9) C(14) C(13) 119.6(8) yes
O(1) C(16) O(2) 124.0(8) yes
O(1) C(16) N(1) 125.0(8) yes
O(2) C(16) N(1) 111.0(8) yes
O(2) C(17) C(18) 107.0(10) yes
O(4) C(19) O(5) 125.0(10) yes
O(4) C(19) O(6) 107.0(10) yes
O(5) C(19) O(6) 127.0(10) yes
O(6) C(20) C(21) 107.0(10) yes
C(6) C(7) H(7A) 120.02 no
C(6) C(7) H(7B) 117.70 no
C(8) C(7) H(7A) 130.20 no
C(8) C(7) H(7B) 110.75 no
H(7A) C(7) H(7B) 110.05 no
C(6) C(8) H(8A) 107.19 no
C(6) C(8) H(8B) 110.54 no
C(7) C(8) H(8A) 104.49 no
C(7) C(8) H(8B) 131.09 no
H(8A) C(8) H(8B) 122.86 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) O(3) 1.487(6) yes
S(1) C(6) 1.783(9) yes
S(1) C(9) 1.783(8) yes
O(1) C(16) 1.220(9) yes
O(2) C(16) 1.342(9) yes
O(2) C(17) 1.450(10) yes
O(4) C(3) 1.441(9) yes
O(4) C(19) 1.320(10) yes
O(5) C(19) 1.200(10) yes
O(6) C(19) 1.320(10) yes
O(6) C(20) 1.530(10) yes
N(1) C(2) 1.459(8) yes
N(1) C(5) 1.463(9) yes
N(1) C(16) 1.335(9) yes
C(2) C(3) 1.536(9) yes
C(2) C(6) 1.530(10) yes
C(3) C(4) 1.510(10) yes
C(4) C(5) 1.520(10) yes
C(6) C(7) 1.510(10) yes
C(6) C(8) 1.510(10) yes
C(7) C(8) 1.480(10) yes
C(9) C(10) 1.380(10) yes
C(9) C(14) 1.380(10) yes
C(10) C(11) 1.380(10) yes
C(11) C(12) 1.380(10) yes
C(12) C(13) 1.370(10) yes
C(12) C(15) 1.530(10) yes
C(13) C(14) 1.370(10) yes
C(17) C(18) 1.42(2) yes
C(20) C(21) 1.22(2) yes
C(7) H(7A) 0.985 no
C(7) H(7B) 1.164 no
C(8) H(8A) 1.140 no
C(8) H(8B) 1.128 no
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
S(1) C(6) C(2) N(1) 59.6(8)
S(1) C(6) C(2) C(3) -60.0(9)
S(1) C(6) C(7) C(8) -106.3(7)
S(1) C(6) C(8) C(7) 100.3(6)
S(1) C(9) C(10) C(11) 175.0(7)
S(1) C(9) C(14) C(13) -175.0(7)
O(1) C(16) O(2) C(17) -1.0(10)
O(1) C(16) N(1) C(2) -10.0(10)
O(1) C(16) N(1) C(5) -171.2(8)
O(2) C(16) N(1) C(2) 172.6(6)
O(2) C(16) N(1) C(5) 11.0(10)
O(3) S(1) C(6) C(2) 52.0(7)
O(3) S(1) C(6) C(7) -89.4(7)
O(3) S(1) C(6) C(8) -153.3(6)
O(3) S(1) C(9) C(10) 12.0(7)
O(3) S(1) C(9) C(14) -175.8(7)
O(4) C(3) C(2) N(1) 87.2(7)
O(4) C(3) C(2) C(6) -146.4(7)
O(4) C(3) C(4) C(5) -81.9(6)
O(4) C(19) O(6) C(20) -170.5(9)
O(5) C(19) O(4) C(3) -8.0(10)
O(5) C(19) O(6) C(20) 9(2)
O(6) C(19) O(4) C(3) 171.7(7)
N(1) C(2) C(3) C(4) -25.2(7)
N(1) C(2) C(6) C(7) -160.6(7)
N(1) C(2) C(6) C(8) -94.1(9)
N(1) C(5) C(4) C(3) -27.5(8)
N(1) C(16) O(2) C(17) 177.3(8)
C(2) N(1) C(5) C(4) 12.2(8)
C(2) C(3) O(4) C(19) 89.5(8)
C(2) C(3) C(4) C(5) 33.0(8)
C(2) C(6) S(1) C(9) -60.9(7)
C(2) C(6) C(7) C(8) 108.8(7)
C(2) C(6) C(8) C(7) -103.7(8)
C(3) C(2) N(1) C(5) 7.9(8)
C(3) C(2) N(1) C(16) -155.6(7)
C(3) C(2) C(6) C(7) 79.9(9)
C(3) C(2) C(6) C(8) 146.3(7)
C(4) C(3) O(4) C(19) -158.1(7)
C(4) C(3) C(2) C(6) 101.3(8)
C(4) C(5) N(1) C(16) 175.1(7)
C(5) N(1) C(2) C(6) -117.9(7)
C(6) S(1) C(9) C(10) 127.1(7)
C(6) S(1) C(9) C(14) -60.8(8)
C(6) C(2) N(1) C(16) 78.6(9)
C(7) C(6) S(1) C(9) 157.7(6)
C(8) C(6) S(1) C(9) 93.7(6)
C(9) C(10) C(11) C(12) .0(10)
C(9) C(14) C(13) C(12) 1.0(10)
C(10) C(9) C(14) C(13) -3.0(10)
C(10) C(11) C(12) C(13) -2.0(10)
C(10) C(11) C(12) C(15) -180.0(10)
C(11) C(10) C(9) C(14) 3.0(10)
C(11) C(12) C(13) C(14) 2.0(10)
C(14) C(13) C(12) C(15) 179.4(9)
C(16) O(2) C(17) C(18) -152.0(10)
C(19) O(6) C(20) C(21) -128(2)