#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/34/1513489.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_1513489
loop_
_publ_author_name
'Lin, Chia-Chi'
'Hsieh, Tsung-Han'
'Liao, Pen-Yuan'
'Liao, Zhen-Yuan'
'Chang, Chih-Wei'
'Shih, Yu-Chiao'
'Yeh, Wen-Hsiung'
'Chien, Tun-Cheng'
_publ_section_title
;
 Practical Synthesis of N-Substituted Cyanamides via Tiemann Rearrangement
 of Amidoximes.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              892
_journal_page_last               895
_journal_paper_doi               10.1021/ol403645y
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C16 H14 N2 O2 S'
_chemical_formula_sum            'C16 H14 N2 O2 S'
_chemical_formula_weight         298.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.867(7)
_cell_angle_beta                 74.001(6)
_cell_angle_gamma                73.228(7)
_cell_formula_units_Z            2
_cell_length_a                   8.2877(12)
_cell_length_b                   8.7172(16)
_cell_length_c                   10.9347(18)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     725.5(2)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0680
_diffrn_reflns_av_sigmaI/netI    0.1499
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4761
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                1302
_reflns_number_total             2575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403645y_si_003.cif
_cod_data_source_block           a14239
_cod_database_code               1513489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.4084(6) 0.4602(5) 0.7840(4) 0.0248(11) Uani 1 1 d .
C2 C 0.4128(6) 0.3708(6) 0.8891(4) 0.0323(12) Uani 1 1 d .
H2 H 0.5063 0.3567 0.9266 0.039 Uiso 1 1 calc R
C3 C 0.2807(6) 0.3021(6) 0.9392(4) 0.0350(13) Uani 1 1 d .
H3 H 0.2857 0.2379 1.0101 0.042 Uiso 1 1 calc R
C4 C 0.1410(6) 0.3246(6) 0.8885(4) 0.0314(12) Uani 1 1 d .
C5 C -0.0060(6) 0.2511(6) 0.9454(4) 0.0470(15) Uani 1 1 d .
H5A H -0.0929 0.2802 0.8972 0.071 Uiso 1 1 calc R
H5B H -0.0623 0.2917 1.0345 0.071 Uiso 1 1 calc R
H5C H 0.0423 0.1340 0.9412 0.071 Uiso 1 1 calc R
C6 C 0.1362(6) 0.4179(6) 0.7842(4) 0.0343(13) Uani 1 1 d .
H6 H 0.0391 0.4370 0.7499 0.041 Uiso 1 1 calc R
C7 C 0.2696(6) 0.4827(6) 0.7301(4) 0.0339(13) Uani 1 1 d .
H7 H 0.2677 0.5425 0.6566 0.041 Uiso 1 1 calc R
C8 C 0.4178(6) 0.8206(6) 0.8257(5) 0.0328(12) Uani 1 1 d .
C9 C 0.4241(6) 0.8026(6) 0.6038(4) 0.0324(12) Uani 1 1 d .
H9 H 0.4781 0.7436 0.5235 0.039 Uiso 1 1 calc R
C10 C 0.3018(6) 0.9359(6) 0.6094(4) 0.0318(12) Uani 1 1 d .
H10 H 0.2445 0.9907 0.6910 0.038 Uiso 1 1 calc R
C11 C 0.2429(6) 1.0111(6) 0.5011(4) 0.0278(12) Uani 1 1 d .
C12 C 0.3144(6) 0.9414(6) 0.3772(4) 0.0352(13) Uani 1 1 d .
H12 H 0.4058 0.8426 0.3605 0.042 Uiso 1 1 calc R
C13 C 0.2546(7) 1.0137(6) 0.2785(4) 0.0384(13) Uani 1 1 d .
H13 H 0.3043 0.9646 0.1944 0.046 Uiso 1 1 calc R
C14 C 0.1218(6) 1.1581(6) 0.3019(4) 0.0401(14) Uani 1 1 d .
H14 H 0.0801 1.2083 0.2342 0.048 Uiso 1 1 calc R
C15 C 0.0512(6) 1.2279(6) 0.4233(4) 0.0409(14) Uani 1 1 d .
H15 H -0.0387 1.3278 0.4393 0.049 Uiso 1 1 calc R
C16 C 0.1092(6) 1.1548(6) 0.5223(4) 0.0365(13) Uani 1 1 d .
H16 H 0.0569 1.2036 0.6063 0.044 Uiso 1 1 calc R
N1 N 0.4838(5) 0.7375(5) 0.7108(3) 0.0295(10) Uani 1 1 d .
N2 N 0.3616(5) 0.8893(5) 0.9232(4) 0.0425(12) Uani 1 1 d .
O1 O 0.6911(4) 0.5229(4) 0.7959(3) 0.0384(9) Uani 1 1 d .
O2 O 0.6536(4) 0.4838(4) 0.5815(3) 0.0372(9) Uani 1 1 d .
S1 S 0.58220(16) 0.53794(16) 0.71327(11) 0.0309(4) Uani 1 1 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
C2 C1 C7 120.2(4)
C2 C1 S1 120.0(4)
C7 C1 S1 119.7(4)
C3 C2 C1 119.5(4)
C2 C3 C4 121.2(4)
C3 C4 C6 118.7(4)
C3 C4 C5 121.1(5)
C6 C4 C5 120.2(4)
C7 C6 C4 120.9(4)
C6 C7 C1 119.4(4)
N2 C8 N1 179.2(5)
C10 C9 N1 124.4(4)
C9 C10 C11 126.2(4)
C16 C11 C12 118.0(4)
C16 C11 C10 119.5(4)
C12 C11 C10 122.4(5)
C13 C12 C11 121.0(5)
C12 C13 C14 119.9(5)
C15 C14 C13 119.6(5)
C14 C15 C16 120.5(5)
C15 C16 C11 120.9(4)
C8 N1 C9 120.2(4)
C8 N1 S1 115.6(3)
C9 N1 S1 121.2(3)
O1 S1 O2 121.6(2)
O1 S1 N1 106.42(19)
O2 S1 N1 103.98(19)
O1 S1 C1 109.1(2)
O2 S1 C1 110.0(2)
N1 S1 C1 104.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.378(6)
C1 C7 1.396(6)
C1 S1 1.749(4)
C2 C3 1.376(6)
C3 C4 1.380(6)
C4 C6 1.391(6)
C4 C5 1.516(6)
C6 C7 1.371(6)
C8 N2 1.141(5)
C8 N1 1.353(6)
C9 C10 1.292(6)
C9 N1 1.439(5)
C10 C11 1.474(6)
C11 C16 1.386(6)
C11 C12 1.393(6)
C12 C13 1.376(6)
C13 C14 1.385(6)
C14 C15 1.368(6)
C15 C16 1.376(6)
N1 S1 1.698(4)
O1 S1 1.423(3)
O2 S1 1.430(3)
