#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/55/2005575.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_2005575
loop_
_publ_author_name
'Fleming, F. F.'
'Hussain, Z.'
'Mullaney, M.'
'Norman, R. E.'
'Chang, S.-C.'
_publ_contact_author
;
Richard E. Norman
Department of Chemistry and Biochemistry
Duquesne University
Pittsburgh, PA 15282  USA
;
_publ_section_title
(8<i>R</i>,8a<i>S</i>)-Indolizidine-1-spiro-2'-(1',3'-dithiane)-8-carbonitrile
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2849
_journal_page_last               2851
_journal_paper_doi               10.1107/S0108270196007548
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C12 H18 N2 S2'
_chemical_formula_weight         254.41
_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'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 97.18(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.513(3)
_cell_length_b                   11.182(2)
_cell_length_c                   11.206(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.2
_cell_measurement_theta_max      20.50
_cell_measurement_theta_min      16.81
_cell_volume                     1307.0(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1992)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      294
_diffrn_measurement_device       AFC7R
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4997
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        -1.8
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'\y scans (TEXSAN; Molecular Structure Corporation, 1992)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       triangular
_exptl_crystal_F_000             544.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.55
_refine_ls_extinction_coef       0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.92
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.060
_refine_ls_shift/esd_max         0.1240
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
; calc w = 4F^2^/\s^2^(F^2^);
\s^2^(F^2^) = [S^2^(C+R^2^B)+(0.045F^2^)^2^]/Lp^2^, where S = scan rate,
C = total integrated peak count, R = ratio of scan to background
counting times, B = total
background count, Lp = Lorentz-polarization factor
;
_refine_ls_wR_factor_obs         0.076
_reflns_number_observed          2248
_reflns_number_total             4787
_reflns_observed_criterion       I>3.00\s(I)
_cod_data_source_file            bk1249.cif
_cod_data_source_block           Indolizidine
_cod_original_sg_symbol_H-M      'P 21/n  '
_cod_original_formula_sum        'C12 H18 N2 S2 '
_cod_database_code               2005575
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
1/2-x,1/2+y,1/2-z
'   -x,   -y,   -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
S(1) 0.0743(6) 0.0558(5) 0.0506(5) 0.0274(4) 0.0126(4) 0.0108(4)
S(2) 0.0993(7) 0.0395(4) 0.0363(4) 0.0118(4) 0.0170(4) 0.0013(3)
N(1) 0.055(2) 0.0440(10) 0.0360(10) 0.0020(10) 0.0040(10) -0.0018(10)
N(2) 0.113(3) 0.049(2) 0.059(2) 0.008(2) 0.031(2) 0.0080(10)
C(1) 0.053(2) 0.0370(10) 0.0350(10) 0.0060(10) 0.0070(10) 0.0030(10)
C(2) 0.062(2) 0.065(2) 0.053(2) -0.006(2) 0.012(2) 0.008(2)
C(3) 0.066(2) 0.051(2) 0.062(2) -0.010(2) 0.000(2) 0.000(2)
C(5) 0.079(3) 0.065(2) 0.0370(10) 0.016(2) -0.001(2) -0.0090(10)
C(6) 0.094(3) 0.079(3) 0.035(2) 0.023(2) 0.018(2) 0.004(2)
C(7) 0.082(3) 0.071(3) 0.052(2) 0.008(2) 0.034(2) 0.011(2)
C(8) 0.050(2) 0.052(2) 0.044(2) 0.0000(10) 0.0140(10) 0.0040(10)
C(9) 0.050(2) 0.0390(10) 0.0380(10) 0.0080(10) 0.0100(10) 0.0000(10)
C(10) 0.071(2) 0.044(2) 0.041(2) -0.005(2) 0.0190(10) 0.0040(10)
C(11) 0.078(3) 0.061(2) 0.051(2) 0.012(2) 0.004(2) 0.019(2)
C(12) 0.080(3) 0.067(2) 0.042(2) -0.009(2) 0.001(2) 0.012(2)
C(13) 0.098(3) 0.059(2) 0.038(2) 0.006(2) 0.019(2) 0.0030(10)
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
S(1) 0.46482(9) 0.06809(8) 0.17378(8) 0.0599(3) Uani d .
S(2) 0.3473(1) 0.30739(7) 0.21052(7) 0.0576(2) Uani d .
N(1) 0.2379(2) 0.1821(2) -0.0841(2) 0.0453(7) Uani d .
N(2) 0.2944(4) 0.5086(3) -0.0264(3) 0.072(1) Uani d .
C(1) 0.3390(3) 0.1726(2) 0.1189(2) 0.0413(7) Uani d .
C(2) 0.2042(4) 0.1156(4) 0.1047(3) 0.059(1) Uani d .
C(3) 0.1804(4) 0.0818(3) -0.0276(3) 0.060(1) Uani d .
C(5) 0.2497(4) 0.1668(4) -0.2119(3) 0.061(1) Uani d .
C(6) 0.3143(4) 0.2742(4) -0.2582(3) 0.069(1) Uani d .
C(7) 0.4413(4) 0.3024(4) -0.1835(3) 0.066(1) Uani d .
C(8) 0.4246(3) 0.3140(3) -0.0484(3) 0.0481(9) Uani d .
C(9) 0.3627(3) 0.1978(3) -0.0129(2) 0.0417(7) Uani d .
C(10) 0.3495(3) 0.4214(3) -0.0323(3) 0.0510(9) Uani d .
C(11) 0.4404(5) 0.0470(4) 0.3295(3) 0.064(1) Uani d .
C(12) 0.4426(4) 0.1601(4) 0.4016(3) 0.063(1) Uani d .
C(13) 0.3342(5) 0.2433(4) 0.3574(3) 0.064(1) Uani d .
H(1) 0.210(4) 0.045(4) 0.155(4) 0.08(1) Uiso calc C2
H(2) 0.140(4) 0.175(4) 0.117(4) 0.08(1) Uiso calc C2
H(3) 0.232(4) 0.002(4) -0.042(3) 0.08(1) Uiso calc C3
H(4) 0.089(4) 0.075(3) -0.056(3) 0.06(1) Uiso calc C3
H(5) 0.301(4) 0.091(3) -0.227(4) 0.07(1) Uiso calc C5
H(6) 0.156(4) 0.158(3) -0.245(3) 0.07(1) Uiso calc C5
H(7) 0.325(4) 0.257(5) -0.338(4) 0.10(1) Uiso calc C6
H(8) 0.261(4) 0.343(4) -0.251(4) 0.08(1) Uiso calc C6
H(9) 0.480(3) 0.375(4) -0.204(3) 0.07(1) Uiso calc C7
H(10) 0.505(3) 0.232(4) -0.187(3) 0.06(1) Uiso calc C7
H(11) 0.426(3) 0.142(3) -0.034(3) 0.043(8) Uiso calc C9
H(12) 0.504(3) 0.323(3) 0.001(3) 0.050(9) Uiso calc C8
H(13) 0.362(4) 0.007(4) 0.330(4) 0.08(1) Uiso calc C11
H(14) 0.513(5) -0.004(5) 0.349(4) 0.10(1) Uiso calc C11
H(15) 0.432(4) 0.138(4) 0.490(4) 0.08(1) Uiso calc C12
H(16) 0.525(4) 0.204(4) 0.409(4) 0.09(1) Uiso calc C12
H(17) 0.256(3) 0.212(3) 0.350(3) 0.046(10) Uiso calc C13
H(18) 0.321(4) 0.312(4) 0.415(4) 0.09(1) Uiso calc C13
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.003 0.002 'International Tables'
H 0.000 0.000 'International Tables'
S 0.125 0.123 'International Tables'
N 0.006 0.003 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 3 -2
4 3 0
4 1 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
C(1) S(1) C(11) 103.0(2) yes
C(1) S(2) C(13) 100.4(2) yes
C(3) N(1) C(5) 115.2(3) yes
C(3) N(1) C(9) 104.4(2) yes
C(5) N(1) C(9) 111.6(3) yes
S(1) C(1) S(2) 111.2(2) yes
S(1) C(1) C(2) 113.0(2) yes
S(1) C(1) C(9) 104.0(2) yes
S(2) C(1) C(2) 112.3(2) yes
S(2) C(1) C(9) 112.6(2) yes
C(2) C(1) C(9) 103.4(2) yes
C(1) C(2) C(3) 103.9(3) yes
C(1) C(2) H(1) 106(2) no
C(1) C(2) H(2) 110(2) no
C(3) C(2) H(1) 111(2) no
C(3) C(2) H(2) 105(2) no
H(1) C(2) H(2) 118(3) no
N(1) C(3) C(2) 101.9(3) yes
N(1) C(3) H(3) 109(2) no
N(1) C(3) H(4) 111(2) no
C(2) C(3) H(3) 109(2) no
C(2) C(3) H(4) 111(2) no
H(3) C(3) H(4) 112(2) no
N(1) C(5) C(6) 110.0(3) yes
N(1) C(5) H(5) 111(2) no
N(1) C(5) H(6) 99(2) no
C(6) C(5) H(5) 109(2) no
C(6) C(5) H(6) 114(2) no
H(5) C(5) H(6) 111(2) no
C(5) C(6) C(7) 112.3(3) yes
C(5) C(6) H(7) 105(3) no
C(5) C(6) H(8) 108(2) no
C(7) C(6) H(7) 111(2) no
C(7) C(6) H(8) 105(2) no
H(7) C(6) H(8) 112(3) no
C(6) C(7) C(8) 110.9(3) yes
C(6) C(7) H(9) 114(2) no
C(6) C(7) H(10) 110.0(10) no
C(8) C(7) H(9) 105(2) no
C(8) C(7) H(10) 104.0(10) no
H(9) C(7) H(10) 110(3) no
C(7) C(8) C(9) 106.7(3) yes
C(7) C(8) C(10) 108.6(3) yes
C(7) C(8) H(12) 112.0(10) no
C(9) C(8) C(10) 114.4(3) yes
C(9) C(8) H(12) 108.0(10) no
C(10) C(8) H(12) 106.0(10) no
N(1) C(9) C(1) 104.9(2) yes
N(1) C(9) C(8) 110.1(2) yes
N(1) C(9) H(11) 113.0(10) no
C(1) C(9) C(8) 121.7(2) yes
C(1) C(9) H(11) 108.0(10) no
C(8) C(9) H(11) 98.0(10) no
N(2) C(10) C(8) 175.2(3) yes
S(1) C(11) C(12) 114.5(3) yes
S(1) C(11) H(13) 107(2) no
S(1) C(11) H(14) 95(2) no
C(12) C(11) H(13) 110(2) no
C(12) C(11) H(14) 115(2) no
H(13) C(11) H(14) 113(4) no
C(11) C(12) C(13) 112.6(3) yes
C(11) C(12) H(15) 108(2) no
C(11) C(12) H(16) 114(2) no
C(13) C(12) H(15) 106(2) no
C(13) C(12) H(16) 109(2) no
H(15) C(12) H(16) 103(3) no
S(2) C(13) C(12) 113.7(3) yes
S(2) C(13) H(17) 104(2) no
S(2) C(13) H(18) 108(2) no
C(12) C(13) H(17) 116(2) no
C(12) C(13) H(18) 114(2) no
H(17) C(13) H(18) 98(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(1) 1.814(3) yes
S(1) C(11) 1.810(4) yes
S(2) C(1) 1.820(3) yes
S(2) C(13) 1.816(3) yes
N(1) C(3) 1.456(4) yes
N(1) C(5) 1.463(4) yes
N(1) C(9) 1.459(4) yes
N(2) C(10) 1.140(4) yes
C(1) C(2) 1.544(5) yes
C(1) C(9) 1.555(4) yes
C(2) C(3) 1.520(5) yes
C(2) H(1) 0.96(4) no
C(2) H(2) 0.97(4) no
C(3) H(3) 1.07(4) no
C(3) H(4) 0.98(4) no
C(5) C(6) 1.503(6) yes
C(5) H(5) 1.03(4) no
C(5) H(6) 1.01(4) no
C(6) C(7) 1.518(6) yes
C(6) H(7) 0.93(5) no
C(6) H(8) 0.96(4) no
C(7) C(8) 1.550(4) yes
C(7) H(9) 0.95(4) no
C(7) H(10) 1.04(4) no
C(8) C(9) 1.528(4) yes
C(8) C(10) 1.462(5) yes
C(8) H(12) 0.95(3) no
C(9) H(11) 0.96(3) no
C(11) C(12) 1.500(6) yes
C(11) H(13) 0.93(4) no
C(11) H(14) 0.96(5) no
C(12) C(13) 1.506(6) yes
C(12) H(15) 1.04(4) no
C(12) H(16) 0.99(4) no
C(13) H(17) 0.89(3) no
C(13) H(18) 1.02(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10753473