#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007177.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_2007177
loop_
_publ_author_name
'Biedermann, M.'
'Hartung, H.'
'D\"olling, W.'
'Verjus, P.'
_publ_section_title
;
 (<i>R</i>)- and (<i>S</i>)-2-(4-Bromophenyl)-2-oxoethyl
 2-Methoxymethylpyrrolidine-1-dithiocarboxylate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              507
_journal_page_last               509
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C15 H18 Br N O2 S2'
_chemical_formula_sum            'C15 H18 Br N O2 S2'
_chemical_formula_weight         388.33
_chemical_melting_point          363(4)
_chemical_name_systematic
; (R)-2-(4-bromophenyl)-2-oxoethyl 2-methoxymethylpyrrolidine-1-
dithiocarboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7824(7)
_cell_length_b                   10.5830(10)
_cell_length_c                   16.3440(10)
_cell_measurement_reflns_used    80
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      10.2
_cell_volume                     1692.0(2)
_computing_cell_refinement       'STADI4 (Stoe, 1996a)'
_computing_data_collection       'STADI4 (Stoe, 1996a)'
_computing_data_reduction        'X-RED (STOE, 1996b)'
_computing_molecular_graphics    'XP/PC (Siemens, 1990)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Stoe Stadi4 diffractometer'
_diffrn_measurement_method       \q/2\q
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3432
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        6.8
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.68
_exptl_absorpt_correction_T_max  0.466
_exptl_absorpt_correction_T_min  0.396
_exptl_absorpt_correction_type   'empirical via \y scans'
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            brown--yellow
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_refine_diff_density_max         .330
_refine_diff_density_min         -.303
_refine_ls_abs_structure_details
'Flack (1983) parameter = 0.00(2); 1716 Friedel pairs'
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_method     SHELXL93_(Sheldrick,_1993)
_refine_ls_goodness_of_fit_all   1.242
_refine_ls_goodness_of_fit_obs   1.170
_refine_ls_hydrogen_treatment    H_atoms:_see_below
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.294
_refine_ls_restrained_S_obs      1.170
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_obs          0.0623
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0237P)^2^+1.8808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1326
_refine_ls_wR_factor_obs         0.0941
_reflns_number_observed          1891
_reflns_number_total             2969
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    jz1254.cif
_[local]_cod_data_source_block   1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '86--93_C' was changed to '363(4)' -
it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1692.1(2)
_cod_database_code               2007177
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Br1 0.1100(8) 0.1560(11) 0.0736(6) -0.0160(9) 0.0065(7) -0.0264(7)
S1 0.099(2) 0.0725(14) 0.0606(12) 0.0172(13) 0.0056(12) 0.0146(11)
S2 0.0669(13) 0.0704(13) 0.0559(10) 0.0101(12) -0.0016(12) -0.0182(11)
O1 0.077(4) 0.069(4) 0.080(4) 0.001(3) 0.025(3) 0.015(3)
O2 0.092(5) 0.160(6) 0.065(4) -0.048(5) -0.005(4) -0.004(4)
N1 0.063(4) 0.046(3) 0.044(3) 0.003(3) 0.001(3) -0.002(3)
C1 0.060(5) 0.060(5) 0.059(4) 0.011(4) -0.009(4) -0.007(4)
C2 0.071(6) 0.139(10) 0.049(5) -0.002(7) -0.003(4) 0.000(5)
C3 0.099(7) 0.078(6) 0.060(5) -0.011(7) 0.007(6) -0.008(4)
C4 0.099(7) 0.049(5) 0.058(4) -0.008(5) 0.007(5) -0.015(4)
C5 0.071(6) 0.061(5) 0.060(5) 0.016(5) 0.004(4) 0.011(4)
C6 0.142(10) 0.085(7) 0.137(9) 0.005(8) 0.075(8) 0.020(7)
C7 0.050(4) 0.053(5) 0.045(4) 0.002(4) 0.008(4) 0.009(3)
C8 0.070(5) 0.098(7) 0.054(4) 0.009(5) -0.010(4) 0.026(4)
C9 0.057(5) 0.077(6) 0.061(5) -0.001(5) 0.002(5) 0.018(4)
C10 0.046(4) 0.055(5) 0.058(4) 0.001(4) -0.004(4) 0.013(4)
C11 0.053(5) 0.094(7) 0.061(5) -0.011(5) -0.005(4) 0.008(5)
C12 0.052(5) 0.102(7) 0.065(5) -0.005(5) 0.001(4) 0.009(5)
C13 0.069(5) 0.078(6) 0.052(4) 0.006(5) 0.001(5) 0.008(4)
C14 0.064(5) 0.070(6) 0.067(5) -0.008(5) -0.017(5) 0.014(4)
C15 0.043(4) 0.083(6) 0.061(5) 0.002(4) -0.003(4) 0.028(5)
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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Br1 0.13842(12) 0.79678(13) 0.87151(6) 0.1132(5) Uani d . 1 Br
S1 0.2279(3) 0.6001(2) 0.35529(13) 0.0773(7) Uani d . 1 S
S2 0.1195(2) 0.8672(2) 0.36098(12) 0.0644(6) Uani d . 1 S
O1 0.2958(5) 0.8750(5) 0.1105(3) 0.075(2) Uani d . 1 O
O2 0.0150(7) 0.5889(7) 0.4846(3) 0.106(2) Uani d . 1 O
N1 0.1456(6) 0.7233(5) 0.2289(3) 0.0509(14) Uani d . 1 N
C1 0.0850(8) 0.8205(7) 0.1750(4) 0.060(2) Uani d . 1 C
H1 0.0049(8) 0.8572(7) 0.2022(4) 0.071 Uiso calc R 1 H
C2 0.0386(9) 0.7442(10) 0.1031(5) 0.086(3) Uani d . 1 C
H2A 0.0393(9) 0.7950(10) 0.0537(5) 0.103 Uiso calc R 1 H
H2B -0.0532(9) 0.7123(10) 0.1118(5) 0.103 Uiso calc R 1 H
C3 0.1406(10) 0.6356(8) 0.0964(4) 0.079(3) Uani d . 1 C
H3A 0.0984(10) 0.5622(8) 0.0713(4) 0.095 Uiso calc R 1 H
H3B 0.2194(10) 0.6602(8) 0.0641(4) 0.095 Uiso calc R 1 H
C4 0.1815(9) 0.6079(7) 0.1836(4) 0.069(3) Uani d . 1 C
H4A 0.1317(9) 0.5357(7) 0.2047(4) 0.082 Uiso calc R 1 H
H4B 0.2787(9) 0.5909(7) 0.1874(4) 0.082 Uiso calc R 1 H
C5 0.1847(8) 0.9245(7) 0.1547(4) 0.064(2) Uani d . 1 C
H5A 0.1393(8) 0.9890(7) 0.1224(4) 0.077 Uiso calc R 1 H
H5B 0.2175(8) 0.9633(7) 0.2048(4) 0.077 Uiso calc R 1 H
C6 0.3797(11) 0.9695(9) 0.0780(6) 0.121(4) Uani d . 1 C
H6A 0.4538(11) 0.9314(9) 0.0484(6) 0.182 Uiso calc R 1 H
H6B 0.4156(11) 1.0203(9) 0.1217(6) 0.182 Uiso calc R 1 H
H6C 0.3273(11) 1.0217(9) 0.0417(6) 0.182 Uiso calc R 1 H
C7 0.1593(7) 0.7377(6) 0.3093(4) 0.049(2) Uani d . 1 C
C8 0.2459(8) 0.6480(8) 0.4596(4) 0.074(2) Uani d . 1 C
H8A 0.3211(8) 0.6012(8) 0.4836(4) 0.089 Uiso calc R 1 H
H8B 0.2702(8) 0.7368(8) 0.4607(4) 0.089 Uiso calc R 1 H
C9 0.1200(9) 0.6290(8) 0.5125(5) 0.065(2) Uani d . 1 C
C10 0.1299(8) 0.6679(6) 0.6006(4) 0.053(2) Uani d . 1 C
C11 0.0176(8) 0.6497(8) 0.6496(5) 0.069(2) Uani d . 1 C
H11 -0.0600(8) 0.6114(8) 0.6280(5) 0.083 Uiso calc R 1 H
C12 0.0185(9) 0.6871(8) 0.7300(5) 0.073(2) Uani d . 1 C
H12 -0.0588(9) 0.6772(8) 0.7625(5) 0.088 Uiso calc R 1 H
C13 0.1358(9) 0.7396(7) 0.7615(4) 0.066(2) Uani d . 1 C
C14 0.2502(9) 0.7548(7) 0.7146(5) 0.067(2) Uani d . 1 C
H14 0.3289(9) 0.7895(7) 0.7373(5) 0.080 Uiso calc R 1 H
C15 0.2485(7) 0.7183(7) 0.6334(5) 0.063(2) Uani d . 1 C
H15 0.3262(7) 0.7275(7) 0.6011(5) 0.075 Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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_publ_flag
C7 S1 C8 102.0(4) yes
C6 O1 C5 112.4(6) ?
C7 N1 C4 124.7(6) ?
C7 N1 C1 123.4(6) ?
C4 N1 C1 111.9(5) ?
N1 C1 C2 102.4(6) ?
N1 C1 C5 112.3(6) ?
C2 C1 C5 114.6(7) ?
C1 C2 C3 105.3(6) ?
C4 C3 C2 104.6(6) ?
N1 C4 C3 104.6(6) ?
O1 C5 C1 109.9(6) ?
N1 C7 S2 125.1(5) yes
N1 C7 S1 111.3(5) yes
S2 C7 S1 123.6(4) yes
C9 C8 S1 115.2(6) yes
O2 C9 C10 121.1(8) ?
O2 C9 C8 121.6(7) yes
C10 C9 C8 117.2(7) yes
C11 C10 C15 120.0(6) ?
C11 C10 C9 117.9(7) ?
C15 C10 C9 122.1(7) ?
C12 C11 C10 120.8(7) ?
C11 C12 C13 118.7(7) ?
C14 C13 C12 121.5(7) ?
C14 C13 Br1 118.9(6) ?
C12 C13 Br1 119.7(6) ?
C13 C14 C15 119.7(7) ?
C14 C15 C10 119.3(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C13 1.898(7) ?
S1 C7 1.771(7) yes
S1 C8 1.787(7) yes
S2 C7 1.655(7) yes
O1 C6 1.399(9) ?
O1 C5 1.406(8) ?
O2 C9 1.201(9) yes
N1 C7 1.330(7) yes
N1 C4 1.471(8) ?
N1 C1 1.478(8) ?
C1 C2 1.497(10) ?
C1 C5 1.508(10) ?
C2 C3 1.526(12) ?
C3 C4 1.509(10) ?
C8 C9 1.519(10) yes
C9 C10 1.501(10) yes
C10 C11 1.373(9) ?
C10 C15 1.384(9) ?
C11 C12 1.373(10) ?
C12 C13 1.375(11) ?
C13 C14 1.366(10) ?
C14 C15 1.384(10) ?
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
_geom_torsion_publ_flag
C7 N1 C1 C2 -157.0(7) ?
C4 N1 C1 C2 20.0(8) ?
C7 N1 C1 C5 79.6(9) ?
C4 N1 C1 C5 -103.4(7) ?
N1 C1 C2 C3 -31.8(8) ?
C5 C1 C2 C3 90.1(8) ?
C1 C2 C3 C4 32.8(8) ?
C7 N1 C4 C3 177.0(7) ?
C1 N1 C4 C3 0.1(9) ?
C2 C3 C4 N1 -19.9(9) ?
C6 O1 C5 C1 169.9(7) ?
N1 C1 C5 O1 63.2(8) ?
C2 C1 C5 O1 -53.1(9) ?
C4 N1 C7 S2 179.9(6) ?
C1 N1 C7 S2 -3.5(10) ?
C4 N1 C7 S1 0.5(9) ?
C1 N1 C7 S1 177.1(5) ?
C8 S1 C7 N1 176.3(5) yes
C8 S1 C7 S2 -3.2(6) yes
C7 S1 C8 C9 87.1(6) yes
S1 C8 C9 O2 -2.6(11) yes
S1 C8 C9 C10 -180.0(5) yes
O2 C9 C10 C11 3.6(12) yes
C8 C9 C10 C11 -179.1(7) yes
O2 C9 C10 C15 -177.8(8) ?
C8 C9 C10 C15 -0.5(11) ?
C15 C10 C11 C12 3.6(12) ?
C9 C10 C11 C12 -177.8(7) ?
C10 C11 C12 C13 -2.1(13) ?
C11 C12 C13 C14 0.0(13) ?
C11 C12 C13 Br1 178.2(6) ?
C12 C13 C14 C15 0.8(12) ?
Br1 C13 C14 C15 -177.5(6) ?
C13 C14 C15 C10 0.6(11) ?
C11 C10 C15 C14 -2.8(11) ?
C9 C10 C15 C14 178.6(7) ?