#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/34/4023483.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_4023483
loop_
_publ_author_name
'Daniel Kadzimirsz'
'Daniel Kramer'
'Lertnarong Sripanom'
'Iris M. Oppel'
'Pawel Rodziewicz'
'Nikos L. Doltsinis'
'Gerald Dyker'
_publ_section_title
;
 A Domino Annulation Reaction under Willgerodt-Kindler Conditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4644
_journal_page_last               4649
_journal_paper_doi               10.1021/jo8005705
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C18 H18 N2 O2 S2'
_chemical_formula_weight         358.46
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.490(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.056(2)
_cell_length_b                   3.9938(5)
_cell_length_c                   23.829(3)
_cell_measurement_reflns_used    2924
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      36.7
_cell_measurement_theta_min      2.6
_cell_volume                     1605.4(3)
_computing_cell_refinement       'CrysAlis RED 1.171.32, Oxford Diffraction'
_computing_data_collection       'CrysAlis CCD 1.171.32, Oxford Diffraction'
_computing_data_reduction        'CrysAlis RED 1.171.32, Oxford Diffraction'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Sapphire2-CCD, Oxford Diffraction'
_diffrn_measurement_method       '373 images at 1.0 deg. in ω and 15 sec.'
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8141
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale-orange
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.225
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                2084
_reflns_number_total             2892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8005705-File002.cif
_cod_data_source_block           p21n
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023483
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.64820(3) -0.09004(15) 0.06375(2) 0.01903(16) Uani 1 1 d . . .
C02 C 0.74185(12) 0.0883(6) 0.08601(9) 0.0172(5) Uani 1 1 d . . .
C03 C 0.75159(12) 0.1882(6) 0.14139(9) 0.0188(5) Uani 1 1 d . . .
H03 H 0.7983 0.2888 0.1608 0.023 Uiso 1 1 calc R . .
C03A C 0.68226(12) 0.1211(6) 0.16606(9) 0.0185(5) Uani 1 1 d . . .
S04 S 0.65675(3) 0.20256(16) 0.23290(2) 0.02049(16) Uani 1 1 d . . .
C04A C 0.56321(12) 0.0304(6) 0.21223(9) 0.0180(5) Uani 1 1 d . . .
C04B C 0.50213(13) -0.0018(6) 0.24691(9) 0.0203(5) Uani 1 1 d . . .
C05 C 0.50807(13) 0.1096(6) 0.30367(9) 0.0251(6) Uani 1 1 d . . .
H05 H 0.5555 0.2136 0.3213 0.030 Uiso 1 1 calc R . .
C06 C 0.44601(14) 0.0689(7) 0.33341(10) 0.0288(6) Uani 1 1 d . . .
H06 H 0.4504 0.1461 0.3715 0.035 Uiso 1 1 calc R . .
C07 C 0.37591(15) -0.0864(7) 0.30792(10) 0.0295(6) Uani 1 1 d . . .
H07 H 0.3334 -0.1166 0.3291 0.035 Uiso 1 1 calc R . .
C08 C 0.36798(13) -0.1952(6) 0.25280(10) 0.0271(6) Uani 1 1 d . . .
H08 H 0.3200 -0.2981 0.2360 0.033 Uiso 1 1 calc R . .
C08A C 0.43103(13) -0.1547(6) 0.22073(9) 0.0210(5) Uani 1 1 d . . .
N09 N 0.41995(10) -0.2668(5) 0.16515(7) 0.0221(4) Uani 1 1 d . . .
C10 C 0.47785(12) -0.2344(6) 0.13433(9) 0.0188(5) Uani 1 1 d . . .
C10A C 0.55155(12) -0.0851(6) 0.15631(9) 0.0170(5) Uani 1 1 d . . .
C10B C 0.62160(12) -0.0266(6) 0.13083(9) 0.0182(5) Uani 1 1 d . . .
C11 C 0.46363(13) -0.3599(6) 0.07426(9) 0.0249(6) Uani 1 1 d . . .
H11A H 0.4123 -0.4743 0.0672 0.037 Uiso 1 1 calc R . .
H11B H 0.5058 -0.5168 0.0683 0.037 Uiso 1 1 calc R . .
H11C H 0.4635 -0.1705 0.0481 0.037 Uiso 1 1 calc R . .
N12 N 0.79730(10) 0.0922(5) 0.04847(7) 0.0181(4) Uani 1 1 d . . .
C13 C 0.87296(12) 0.2522(6) 0.07072(9) 0.0207(5) Uani 1 1 d . . .
H13A H 0.8933 0.1593 0.1086 0.025 Uiso 1 1 calc R . .
H13B H 0.8649 0.4959 0.0749 0.025 Uiso 1 1 calc R . .
C14 C 0.93221(12) 0.1912(6) 0.03078(9) 0.0231(5) Uani 1 1 d . . .
H14A H 0.9825 0.3062 0.0454 0.028 Uiso 1 1 calc R . .
H14B H 0.9432 -0.0517 0.0293 0.028 Uiso 1 1 calc R . .
O15 O 0.90408(8) 0.3092(4) -0.02505(6) 0.0239(4) Uani 1 1 d . . .
C16 C 0.83292(12) 0.1354(6) -0.04724(9) 0.0238(5) Uani 1 1 d . . .
H16A H 0.8442 -0.1072 -0.0491 0.029 Uiso 1 1 calc R . .
H16B H 0.8141 0.2147 -0.0863 0.029 Uiso 1 1 calc R . .
C17 C 0.76853(12) 0.1908(6) -0.01067(8) 0.0213(5) Uani 1 1 d . . .
H17A H 0.7530 0.4298 -0.0119 0.026 Uiso 1 1 calc R . .
H17B H 0.7212 0.0564 -0.0256 0.026 Uiso 1 1 calc R . .
O1 O 0.29345(11) 0.2833(6) 0.12436(9) 0.0432(5) Uani 1 1 d D . .
H1A H 0.3312(12) 0.409(6) 0.1352(12) 0.052 Uiso 1 1 d D . .
H1B H 0.3132(16) 0.107(4) 0.1381(12) 0.052 Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10B S01 C02 90.71(10) . . ?
C03 C02 N12 128.3(2) . . ?
C03 C02 S01 112.67(15) . . ?
N12 C02 S01 118.89(16) . . ?
C02 C03 C03A 110.8(2) . . ?
C10B C03A C03 115.34(18) . . ?
C10B C03A S04 111.94(15) . . ?
C03 C03A S04 132.68(17) . . ?
C04A S04 C03A 90.55(10) . . ?
C10A C04A C04B 120.6(2) . . ?
C10A C04A S04 113.34(15) . . ?
C04B C04A S04 126.04(17) . . ?
C05 C04B C08A 119.51(19) . . ?
C05 C04B C04A 124.8(2) . . ?
C08A C04B C04A 115.72(19) . . ?
C06 C05 C04B 120.5(2) . . ?
C05 C06 C07 120.2(2) . . ?
C08 C07 C06 120.8(2) . . ?
C07 C08 C08A 120.3(2) . . ?
N09 C08A C04B 123.19(18) . . ?
N09 C08A C08 118.1(2) . . ?
C04B C08A C08 118.7(2) . . ?
C10 N09 C08A 119.50(19) . . ?
N09 C10 C10A 122.00(19) . . ?
N09 C10 C11 117.92(19) . . ?
C10A C10 C11 120.08(18) . . ?
C04A C10A C10 118.97(18) . . ?
C04A C10A C10B 109.84(19) . . ?
C10 C10A C10B 131.2(2) . . ?
C03A C10B C10A 114.32(18) . . ?
C03A C10B S01 110.50(15) . . ?
C10A C10B S01 135.15(18) . . ?
C02 N12 C13 114.62(17) . . ?
C02 N12 C17 117.00(16) . . ?
C13 N12 C17 112.31(16) . . ?
N12 C13 C14 109.73(17) . . ?
O15 C14 C13 111.79(17) . . ?
C14 O15 C16 109.57(16) . . ?
O15 C16 C17 111.34(18) . . ?
N12 C17 C16 110.06(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S01 C10B 1.743(2) . ?
S01 C02 1.758(2) . ?
C02 C03 1.365(3) . ?
C02 N12 1.394(2) . ?
C03 C03A 1.421(3) . ?
C03A C10B 1.366(3) . ?
C03A S04 1.743(2) . ?
S04 C04A 1.740(2) . ?
C04A C10A 1.396(3) . ?
C04A C04B 1.428(3) . ?
C04B C05 1.413(3) . ?
C04B C08A 1.417(3) . ?
C05 C06 1.367(3) . ?
C06 C07 1.403(3) . ?
C07 C08 1.371(3) . ?
C08 C08A 1.417(3) . ?
C08A N09 1.384(3) . ?
N09 C10 1.321(2) . ?
C10 C10A 1.420(3) . ?
C10 C11 1.502(3) . ?
C10A C10B 1.437(3) . ?
N12 C13 1.467(3) . ?
N12 C17 1.476(3) . ?
C13 C14 1.507(3) . ?
C14 O15 1.426(3) . ?
O15 C16 1.430(3) . ?
C16 C17 1.516(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10B S01 C02 C03 0.19(18) . . . . ?
C10B S01 C02 N12 176.12(18) . . . . ?
N12 C02 C03 C03A -175.8(2) . . . . ?
S01 C02 C03 C03A -0.3(3) . . . . ?
C02 C03 C03A C10B 0.3(3) . . . . ?
C02 C03 C03A S04 -177.19(19) . . . . ?
C10B C03A S04 C04A 0.43(18) . . . . ?
C03 C03A S04 C04A 178.0(2) . . . . ?
C03A S04 C04A C10A -0.08(18) . . . . ?
C03A S04 C04A C04B 179.1(2) . . . . ?
C10A C04A C04B C05 -179.4(2) . . . . ?
S04 C04A C04B C05 1.4(4) . . . . ?
C10A C04A C04B C08A -0.1(3) . . . . ?
S04 C04A C04B C08A -179.26(17) . . . . ?
C08A C04B C05 C06 0.4(4) . . . . ?
C04A C04B C05 C06 179.7(2) . . . . ?
C04B C05 C06 C07 0.5(4) . . . . ?
C05 C06 C07 C08 -1.0(4) . . . . ?
C06 C07 C08 C08A 0.6(4) . . . . ?
C05 C04B C08A N09 179.1(2) . . . . ?
C04A C04B C08A N09 -0.2(3) . . . . ?
C05 C04B C08A C08 -0.8(3) . . . . ?
C04A C04B C08A C08 179.9(2) . . . . ?
C07 C08 C08A N09 -179.6(2) . . . . ?
C07 C08 C08A C04B 0.3(4) . . . . ?
C04B C08A N09 C10 0.5(4) . . . . ?
C08 C08A N09 C10 -179.6(2) . . . . ?
C08A N09 C10 C10A -0.5(3) . . . . ?
C08A N09 C10 C11 179.8(2) . . . . ?
C04B C04A C10A C10 0.2(3) . . . . ?
S04 C04A C10A C10 179.41(17) . . . . ?
C04B C04A C10A C10B -179.5(2) . . . . ?
S04 C04A C10A C10B -0.3(2) . . . . ?
N09 C10 C10A C04A 0.1(3) . . . . ?
C11 C10 C10A C04A 179.8(2) . . . . ?
N09 C10 C10A C10B 179.7(2) . . . . ?
C11 C10 C10A C10B -0.6(4) . . . . ?
C03 C03A C10B C10A -178.7(2) . . . . ?
S04 C03A C10B C10A -0.7(3) . . . . ?
C03 C03A C10B S01 -0.1(3) . . . . ?
S04 C03A C10B S01 177.86(12) . . . . ?
C04A C10A C10B C03A 0.6(3) . . . . ?
C10 C10A C10B C03A -179.0(2) . . . . ?
C04A C10A C10B S01 -177.4(2) . . . . ?
C10 C10A C10B S01 2.9(4) . . . . ?
C02 S01 C10B C03A -0.03(18) . . . . ?
C02 S01 C10B C10A 178.1(2) . . . . ?
C03 C02 N12 C13 -5.9(3) . . . . ?
S01 C02 N12 C13 178.87(16) . . . . ?
C03 C02 N12 C17 -140.5(2) . . . . ?
S01 C02 N12 C17 44.3(3) . . . . ?
C02 N12 C13 C14 170.66(18) . . . . ?
C17 N12 C13 C14 -52.6(2) . . . . ?
N12 C13 C14 O15 57.1(2) . . . . ?
C13 C14 O15 C16 -61.0(2) . . . . ?
C14 O15 C16 C17 60.1(2) . . . . ?
C02 N12 C17 C16 -172.16(19) . . . . ?
C13 N12 C17 C16 52.2(2) . . . . ?
O15 C16 C17 N12 -55.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658686
