#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011997.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_2011997
loop_
_publ_author_name
'Linden, Anthony'
'Ghorbani-Salman Pour, Fatemeh'
'Breitenmoser, Roland A.'
'Heimgartner, Heinz'
_publ_section_title
;
 (+-)-6-Benzyl-3,3-dimethylmorpholine-2,5-dione and its 5-monothio and
 2,5-dithio derivatives
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              634
_journal_page_last               637
_journal_paper_doi               10.1107/S0108270101003195
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C13 H15 N O S2'
_chemical_formula_sum            'C13 H15 N O S2'
_chemical_formula_weight         265.39
_chemical_melting_point          396.5(5)
_chemical_name_systematic
;
6-benzyl-3,3-dimethylmorpholine-2,5-dithione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.62(2)
_cell_angle_beta                 76.211(16)
_cell_angle_gamma                84.971(18)
_cell_formula_units_Z            4
_cell_length_a                   8.6915(13)
_cell_length_b                   11.896(3)
_cell_length_c                   13.661(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      19.0
_cell_volume                     1328.2(6)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
; MSC/AFC Diffractometer Control Software (Molecular
Structure Corporation, 1991)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173.0(10)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Rigaku AFC-5R diffractometer'
_diffrn_measurement_method       'ω--2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0207
_diffrn_reflns_av_sigmaI/netI    .0440
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6399
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .384
_exptl_absorpt_correction_T_max  .891
_exptl_absorpt_correction_T_min  .781
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .30
_refine_diff_density_max         .540
_refine_diff_density_min         -.405
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         6101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          .0802
_refine_ls_R_factor_gt           .0487
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0823P)²+0.0825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1421
_reflns_number_gt                4424
_reflns_number_total             6101
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk1460.cif
_cod_data_source_block           VI
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '396-397' was changed to '396.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '396-397' was changed to '396.5(5)' -
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_database_code               2011997
_cod_database_fobs_code          2011997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S2 1.31149(7) .61456(6) .69359(6) .04615(19) Uani d . 1 . . S
S5 .78907(7) .39220(5) .58055(6) .03978(18) Uani d . 1 . . S
O1 1.02831(18) .60055(13) .67956(16) .0411(4) Uani d . 1 . . O
N4 1.0494(2) .37797(15) .65169(16) .0297(4) Uani d . 1 . . N
H4 1.064(4) .310(3) .634(2) .057(9) Uiso d . 1 . . H
C2 1.1665(3) .54387(19) .68373(19) .0322(5) Uani d . 1 . . C
C3 1.1772(2) .41325(18) .69084(19) .0296(5) Uani d . 1 . . C
C5 .9228(2) .43916(18) .62984(19) .0318(5) Uani d . 1 . . C
C6 .8992(3) .56035(19) .6472(2) .0381(6) Uani d . 1 . . C
H6 .8919 .6136 .5791 .046 Uiso calc R 1 . . H
C7 1.3348(3) .3776(2) .6257(2) .0355(5) Uani d . 1 . . C
H71 1.3472 .4220 .5537 .053 Uiso calc R 1 . . H
H72 1.3354 .2945 .6283 .053 Uiso calc R 1 . . H
H73 1.4225 .3935 .6535 .053 Uiso calc R 1 . . H
C8 1.1591(3) .3487(2) .8052(2) .0429(6) Uani d . 1 . . C
H81 1.1635 .2648 .8109 .064 Uiso calc R 1 . . H
H82 1.0570 .3709 .8457 .064 Uiso calc R 1 . . H
H83 1.2452 .3693 .8320 .064 Uiso calc R 1 . . H
C9 .7450(3) .5789(2) .7248(3) .0504(8) Uani d . 1 . . C
H91 .7367 .6612 .7288 .060 Uiso calc R 1 . . H
H92 .6547 .5646 .6974 .060 Uiso calc R 1 . . H
C10 .7289(3) .5037(2) .8330(2) .0474(7) Uani d . 1 . . C
C11 .6270(3) .4108(2) .8676(3) .0544(8) Uani d . 1 . . C
H11 .5719 .3923 .8217 .065 Uiso calc R 1 . . H
C12 .6056(4) .3452(3) .9691(3) .0633(9) Uani d . 1 . . C
H12 .5350 .2825 .9919 .076 Uiso calc R 1 . . H
C13 .6837(4) .3690(3) 1.0358(3) .0679(10) Uani d . 1 . . C
H13 .6681 .3234 1.1050 .082 Uiso calc R 1 . . H
C14 .7868(4) .4606(3) 1.0026(3) .0729(11) Uani d . 1 . . C
H14 .8426 .4777 1.0488 .088 Uiso calc R 1 . . H
C15 .8079(3) .5266(3) .9026(3) .0617(9) Uani d . 1 . . C
H15 .8783 .5894 .8806 .074 Uiso calc R 1 . . H
S22 .51036(7) -.14157(5) .71819(7) .0507(2) Uani d . 1 . . S
S25 1.14229(6) .11719(5) .57744(5) .03136(15) Uani d . 1 . . S
O21 .80999(16) -.12851(12) .68707(13) .0299(3) Uani d . 1 . . O
N24 .83142(19) .10772(15) .62064(14) .0252(4) Uani d . 1 . . N
H24 .838(3) .186(2) .598(2) .039(7) Uiso d . 1 . . H
C22 .6729(2) -.06953(18) .68532(18) .0283(4) Uani d . 1 . . C
C23 .6698(2) .06227(17) .65390(16) .0246(4) Uani d . 1 . . C
C25 .9671(2) .05103(18) .62203(16) .0246(4) Uani d . 1 . . C
C26 .9652(2) -.07851(18) .66533(18) .0278(4) Uani d . 1 . . C
H26 1.0381 -.1152 .6126 .033 Uiso calc R 1 . . H
C27 .5915(3) .10592(19) .56134(18) .0303(5) Uani d . 1 . . C
H271 .5911 .1910 .5416 .045 Uiso calc R 1 . . H
H272 .4823 .0796 .5806 .045 Uiso calc R 1 . . H
H273 .6511 .0751 .5027 .045 Uiso calc R 1 . . H
C28 .5812(3) .11054(19) .74677(17) .0302(5) Uani d . 1 . . C
H281 .4702 .0881 .7657 .045 Uiso calc R 1 . . H
H282 .5862 .1954 .7283 .045 Uiso calc R 1 . . H
H283 .6306 .0789 .8057 .045 Uiso calc R 1 . . H
C29 1.0253(3) -.11551(19) .76561(18) .0310(5) Uani d . 1 . . C
H291 1.0276 -.2013 .7880 .037 Uiso calc R 1 . . H
H292 1.1352 -.0895 .7517 .037 Uiso calc R 1 . . H
C30 .9237(3) -.06613(19) .85260(17) .0295(5) Uani d . 1 . . C
C31 .9515(3) .0432(2) .86368(18) .0340(5) Uani d . 1 . . C
H31 1.0376 .0862 .8173 .041 Uiso calc R 1 . . H
C32 .8556(3) .0904(2) .94128(19) .0393(5) Uani d . 1 . . C
H32 .8760 .1652 .9475 .047 Uiso calc R 1 . . H
C33 .7303(3) .0285(2) 1.00955(19) .0388(5) Uani d . 1 . . C
H33 .6640 .0609 1.0624 .047 Uiso calc R 1 . . H
C34 .7020(3) -.0810(2) 1.00048(19) .0401(6) Uani d . 1 . . C
H34 .6169 -.1241 1.0479 .048 Uiso calc R 1 . . H
C35 .7973(3) -.1280(2) .92259(19) .0356(5) Uani d . 1 . . C
H35 .7765 -.2028 .9168 .043 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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H .0000 .0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N .0061 .0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O .0106 .0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
S S .1246 .1234
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 2 -2
-2 3 -2
-2 -1 -2
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
C2 O1 C6 124.91(18) yes
C5 N4 C3 128.14(19) yes
C5 N4 H4 115(2) ?
C3 N4 H4 117(2) ?
O1 C2 C3 119.02(19) ?
O1 C2 S2 117.96(17) ?
C3 C2 S2 122.68(16) ?
N4 C3 C2 110.90(17) ?
N4 C3 C7 107.16(18) ?
C2 C3 C7 111.39(18) ?
N4 C3 C8 108.33(18) ?
C2 C3 C8 108.7(2) ?
C7 C3 C8 110.28(19) ?
N4 C5 C6 118.2(2) ?
N4 C5 S5 124.03(18) ?
C6 C5 S5 117.72(16) ?
O1 C6 C5 114.97(18) ?
O1 C6 C9 107.5(2) ?
C5 C6 C9 113.86(19) ?
O1 C6 H6 106.6 ?
C5 C6 H6 106.6 ?
C9 C6 H6 106.6 ?
C3 C7 H71 109.5 ?
C3 C7 H72 109.5 ?
H71 C7 H72 109.5 ?
C3 C7 H73 109.5 ?
H71 C7 H73 109.5 ?
H72 C7 H73 109.5 ?
C3 C8 H81 109.5 ?
C3 C8 H82 109.5 ?
H81 C8 H82 109.5 ?
C3 C8 H83 109.5 ?
H81 C8 H83 109.5 ?
H82 C8 H83 109.5 ?
C10 C9 C6 115.5(2) ?
C10 C9 H91 108.4 ?
C6 C9 H91 108.4 ?
C10 C9 H92 108.4 ?
C6 C9 H92 108.4 ?
H91 C9 H92 107.5 ?
C15 C10 C11 117.8(3) ?
C15 C10 C9 122.0(2) ?
C11 C10 C9 120.2(3) ?
C12 C11 C10 120.3(3) ?
C12 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
C13 C12 C11 121.1(3) ?
C13 C12 H12 119.5 ?
C11 C12 H12 119.5 ?
C12 C13 C14 119.5(4) ?
C12 C13 H13 120.2 ?
C14 C13 H13 120.2 ?
C15 C14 C13 119.8(4) ?
C15 C14 H14 120.1 ?
C13 C14 H14 120.1 ?
C14 C15 C10 121.5(3) ?
C14 C15 H15 119.2 ?
C10 C15 H15 119.2 ?
C22 O21 C26 126.03(16) yes
C25 N24 C23 128.93(18) yes
C25 N24 H24 115.1(17) ?
C23 N24 H24 115.9(17) ?
O21 C22 C23 120.13(18) ?
O21 C22 S22 118.61(15) ?
C23 C22 S22 121.26(15) ?
N24 C23 C22 111.51(16) ?
N24 C23 C28 108.02(17) ?
C22 C23 C28 109.37(18) ?
N24 C23 C27 106.60(17) ?
C22 C23 C27 110.35(18) ?
C28 C23 C27 110.96(17) ?
N24 C25 C26 118.26(18) ?
N24 C25 S25 122.55(16) ?
C26 C25 S25 119.19(15) ?
O21 C26 C25 114.31(16) ?
O21 C26 C29 106.92(17) ?
C25 C26 C29 112.68(17) ?
O21 C26 H26 107.5 ?
C25 C26 H26 107.5 ?
C29 C26 H26 107.5 ?
C23 C27 H271 109.5 ?
C23 C27 H272 109.5 ?
H271 C27 H272 109.5 ?
C23 C27 H273 109.5 ?
H271 C27 H273 109.5 ?
H272 C27 H273 109.5 ?
C23 C28 H281 109.5 ?
C23 C28 H282 109.5 ?
H281 C28 H282 109.5 ?
C23 C28 H283 109.5 ?
H281 C28 H283 109.5 ?
H282 C28 H283 109.5 ?
C30 C29 C26 112.80(17) ?
C30 C29 H291 109.0 ?
C26 C29 H291 109.0 ?
C30 C29 H292 109.0 ?
C26 C29 H292 109.0 ?
H291 C29 H292 107.8 ?
C31 C30 C35 118.2(2) ?
C31 C30 C29 120.9(2) ?
C35 C30 C29 120.8(2) ?
C32 C31 C30 121.1(2) ?
C32 C31 H31 119.4 ?
C30 C31 H31 119.4 ?
C33 C32 C31 120.0(2) ?
C33 C32 H32 120.0 ?
C31 C32 H32 120.0 ?
C32 C33 C34 119.7(2) ?
C32 C33 H33 120.2 ?
C34 C33 H33 120.2 ?
C33 C34 C35 120.4(2) ?
C33 C34 H34 119.8 ?
C35 C34 H34 119.8 ?
C34 C35 C30 120.6(2) ?
C34 C35 H35 119.7 ?
C30 C35 H35 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S2 C2 . 1.624(2) yes
S5 C5 . 1.670(2) yes
O1 C2 . 1.331(3) yes
O1 C6 . 1.455(3) yes
N4 C5 . 1.319(3) yes
N4 C3 . 1.473(3) yes
N4 H4 . .89(3) ?
C2 C3 . 1.529(3) ?
C3 C7 . 1.534(3) ?
C3 C8 . 1.538(3) ?
C5 C6 . 1.507(3) ?
C6 C9 . 1.534(3) ?
C6 H6 . 1.0000 ?
C7 H71 . .9800 ?
C7 H72 . .9800 ?
C7 H73 . .9800 ?
C8 H81 . .9800 ?
C8 H82 . .9800 ?
C8 H83 . .9800 ?
C9 C10 . 1.508(4) ?
C9 H91 . .9900 ?
C9 H92 . .9900 ?
C10 C15 . 1.386(4) ?
C10 C11 . 1.393(3) ?
C11 C12 . 1.389(5) ?
C11 H11 . .9500 ?
C12 C13 . 1.352(5) ?
C12 H12 . .9500 ?
C13 C14 . 1.389(5) ?
C13 H13 . .9500 ?
C14 C15 . 1.375(5) ?
C14 H14 . .9500 ?
C15 H15 . .9500 ?
S22 C22 . 1.628(2) yes
S25 C25 . 1.685(2) yes
O21 C22 . 1.331(2) yes
O21 C26 . 1.458(2) yes
N24 C25 . 1.308(3) yes
N24 C23 . 1.476(2) yes
N24 H24 . .91(3) ?
C22 C23 . 1.519(3) ?
C23 C28 . 1.533(3) ?
C23 C27 . 1.534(3) ?
C25 C26 . 1.507(3) ?
C26 C29 . 1.531(3) ?
C26 H26 . 1.0000 ?
C27 H271 . .9800 ?
C27 H272 . .9800 ?
C27 H273 . .9800 ?
C28 H281 . .9800 ?
C28 H282 . .9800 ?
C28 H283 . .9800 ?
C29 C30 . 1.514(3) ?
C29 H291 . .9900 ?
C29 H292 . .9900 ?
C30 C31 . 1.394(3) ?
C30 C35 . 1.398(3) ?
C31 C32 . 1.388(3) ?
C31 H31 . .9500 ?
C32 C33 . 1.383(3) ?
C32 H32 . .9500 ?
C33 C34 . 1.387(4) ?
C33 H33 . .9500 ?
C34 C35 . 1.387(3) ?
C34 H34 . .9500 ?
C35 H35 . .9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4 S25 .89(3) 2.58(3) 3.469(2) 173(3) yes
N24 H24 S5 .91(3) 2.42(3) 3.293(2) 163(2) yes
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
C6 O1 C2 C3 -21.4(4)
C6 O1 C2 S2 165.11(19)
C5 N4 C3 C2 -11.8(3)
C5 N4 C3 C7 -133.6(2)
C5 N4 C3 C8 107.4(3)
O1 C2 C3 N4 22.2(3)
S2 C2 C3 N4 -164.59(17)
O1 C2 C3 C7 141.5(2)
S2 C2 C3 C7 -45.3(3)
O1 C2 C3 C8 -96.8(3)
S2 C2 C3 C8 76.4(2)
C3 N4 C5 C6 -1.0(4)
C3 N4 C5 S5 177.11(19)
C2 O1 C6 C5 7.2(4)
C2 O1 C6 C9 135.2(2)
N4 C5 C6 O1 4.6(3)
S5 C5 C6 O1 -173.61(17)
N4 C5 C6 C9 -120.1(3)
S5 C5 C6 C9 61.7(3)
O1 C6 C9 C10 -67.7(3)
C5 C6 C9 C10 60.9(3)
C6 C9 C10 C15 77.1(3)
C6 C9 C10 C11 -105.8(3)
C15 C10 C11 C12 .7(4)
C9 C10 C11 C12 -176.6(3)
C10 C11 C12 C13 -.6(5)
C11 C12 C13 C14 .1(5)
C12 C13 C14 C15 .4(5)
C13 C14 C15 C10 -.3(5)
C11 C10 C15 C14 -.2(4)
C9 C10 C15 C14 177.0(3)
C26 O21 C22 C23 2.9(3)
C26 O21 C22 S22 -176.68(16)
C25 N24 C23 C22 -4.9(3)
C25 N24 C23 C28 115.3(2)
C25 N24 C23 C27 -125.4(2)
O21 C22 C23 N24 4.4(3)
S22 C22 C23 N24 -176.09(16)
O21 C22 C23 C28 -115.0(2)
S22 C22 C23 C28 64.5(2)
O21 C22 C23 C27 122.6(2)
S22 C22 C23 C27 -57.8(2)
C23 N24 C25 C26 -1.8(3)
C23 N24 C25 S25 178.19(16)
C22 O21 C26 C25 -9.6(3)
C22 O21 C26 C29 115.9(2)
N24 C25 C26 O21 8.7(3)
S25 C25 C26 O21 -171.28(14)
N24 C25 C26 C29 -113.6(2)
S25 C25 C26 C29 66.4(2)
O21 C26 C29 C30 -64.3(2)
C25 C26 C29 C30 62.1(2)
C26 C29 C30 C31 -86.9(3)
C26 C29 C30 C35 91.7(2)
C35 C30 C31 C32 -.7(3)
C29 C30 C31 C32 178.0(2)
C30 C31 C32 C33 .3(4)
C31 C32 C33 C34 .5(4)
C32 C33 C34 C35 -.8(4)
C33 C34 C35 C30 .4(4)
C31 C30 C35 C34 .3(3)
C29 C30 C35 C34 -178.3(2)
