#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/34/1513487.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_1513487
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         'C14 H12 Cl N3 O2 S'
_chemical_formula_sum            'C14 H12 Cl N3 O2 S'
_chemical_formula_weight         321.78
_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                69.299(2)
_cell_angle_beta                 67.831(2)
_cell_angle_gamma                72.037(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7956(9)
_cell_length_b                   10.4442(11)
_cell_length_c                   10.9339(11)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     852.17(15)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5714
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.9328
_exptl_absorpt_correction_T_min  0.8407
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.247
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.847
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.847
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0525
_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)+(0.1071P)²+2.1273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1634
_reflns_number_gt                2576
_reflns_number_total             2971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403645y_si_005.cif
_cod_data_source_block           a13713
_cod_database_code               1513487
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 0.0174(4) 0.2664(3) 0.8162(3) 0.0283(6) Uani 1 1 d .
C2 C 0.0588(4) 0.1644(4) 0.9269(3) 0.0374(8) Uani 1 1 d .
H2 H 0.1264 0.0760 0.9164 0.045 Uiso 1 1 calc R
C3 C 0.0001(5) 0.1928(4) 1.0537(4) 0.0447(9) Uani 1 1 d .
H3 H 0.0289 0.1235 1.1299 0.054 Uiso 1 1 calc R
C4 C -0.0998(5) 0.3209(4) 1.0703(4) 0.0458(9) Uani 1 1 d .
C5 C -0.1639(6) 0.3485(6) 1.2093(4) 0.0686(13) Uani 1 1 d .
H5A H -0.2327 0.4430 1.2035 0.103 Uiso 1 1 calc R
H5B H -0.0688 0.3402 1.2396 0.103 Uiso 1 1 calc R
H5C H -0.2318 0.2802 1.2753 0.103 Uiso 1 1 calc R
C6 C -0.1376(5) 0.4209(4) 0.9576(4) 0.0548(10) Uani 1 1 d .
H6 H -0.2049 0.5093 0.9682 0.066 Uiso 1 1 calc R
C7 C -0.0804(4) 0.3963(4) 0.8289(4) 0.0433(8) Uani 1 1 d .
H7 H -0.1075 0.4662 0.7523 0.052 Uiso 1 1 calc R
C8 C 0.3672(4) 0.3443(3) 0.5557(3) 0.0255(6) Uani 1 1 d .
C9 C 0.5638(4) 0.1649(3) 0.5930(3) 0.0263(6) Uani 1 1 d .
C10 C 0.7161(4) 0.0770(4) 0.6034(3) 0.0354(7) Uani 1 1 d .
H10 H 0.8137 0.1137 0.5768 0.042 Uiso 1 1 calc R
C11 C 0.7214(4) -0.0655(4) 0.6537(3) 0.0380(8) Uani 1 1 d .
H11 H 0.8237 -0.1278 0.6627 0.046 Uiso 1 1 calc R
C12 C 0.5797(4) -0.1175(3) 0.6909(3) 0.0342(7) Uani 1 1 d .
C13 C 0.4259(4) -0.0335(3) 0.6800(3) 0.0297(7) Uani 1 1 d .
H13 H 0.3294 -0.0710 0.7051 0.036 Uiso 1 1 calc R
C14 C 0.4230(3) 0.1081(3) 0.6303(3) 0.0242(6) Uani 1 1 d .
N1 N 0.2945(3) 0.2255(2) 0.6030(2) 0.0245(5) Uani 1 1 d .
N2 N 0.2794(3) 0.4743(3) 0.5270(3) 0.0324(6) Uani 1 1 d .
H2A H 0.3283 0.5457 0.5000 0.039 Uiso 1 1 calc R
H2B H 0.1725 0.4889 0.5350 0.039 Uiso 1 1 calc R
N3 N 0.5262(3) 0.3103(3) 0.5475(3) 0.0287(6) Uani 1 1 d .
O1 O 0.0755(3) 0.0890(2) 0.6784(2) 0.0332(5) Uani 1 1 d .
O2 O 0.0193(3) 0.3413(2) 0.5623(2) 0.0339(5) Uani 1 1 d .
S1 S 0.08906(8) 0.22780(7) 0.65825(7) 0.0256(2) Uani 1 1 d .
Cl1 Cl 0.59326(13) -0.29757(9) 0.75486(10) 0.0503(3) 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'
Cl Cl 0.1484 0.1585 '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
C7 C1 C2 121.5(3)
C7 C1 S1 120.0(3)
C2 C1 S1 118.5(2)
C1 C2 C3 119.1(3)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 120.9(3)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C6 118.6(3)
C3 C4 C5 119.9(4)
C6 C4 C5 121.6(4)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 C7 122.1(4)
C4 C6 H6 118.9
C7 C6 H6 118.9
C1 C7 C6 117.8(3)
C1 C7 H7 121.1
C6 C7 H7 121.1
N3 C8 N2 125.3(3)
N3 C8 N1 112.1(2)
N2 C8 N1 122.6(3)
C10 C9 N3 128.8(3)
C10 C9 C14 119.9(3)
N3 C9 C14 111.3(2)
C9 C10 C11 118.0(3)
C9 C10 H10 121.0
C11 C10 H10 121.0
C10 C11 C12 120.5(3)
C10 C11 H11 119.7
C12 C11 H11 119.7
C13 C12 C11 123.2(3)
C13 C12 Cl1 118.2(3)
C11 C12 Cl1 118.5(2)
C14 C13 C12 115.4(3)
C14 C13 H13 122.3
C12 C13 H13 122.3
C13 C14 C9 123.0(3)
C13 C14 N1 132.6(3)
C9 C14 N1 104.4(2)
C8 N1 C14 106.1(2)
C8 N1 S1 125.3(2)
C14 N1 S1 126.3(2)
C8 N2 H2A 120.0
C8 N2 H2B 120.0
H2A N2 H2B 120.0
C8 N3 C9 106.0(2)
O1 S1 O2 120.10(13)
O1 S1 N1 105.50(12)
O2 S1 N1 105.98(12)
O1 S1 C1 109.87(14)
O2 S1 C1 109.42(14)
N1 S1 C1 104.75(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C7 1.386(5)
C1 C2 1.384(4)
C1 S1 1.748(3)
C2 C3 1.390(5)
C2 H2 0.9500
C3 C4 1.386(5)
C3 H3 0.9500
C4 C6 1.380(6)
C4 C5 1.508(5)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.394(5)
C6 H6 0.9500
C7 H7 0.9500
C8 N3 1.308(4)
C8 N2 1.332(4)
C8 N1 1.415(4)
C9 C10 1.391(4)
C9 N3 1.394(4)
C9 C14 1.397(4)
C10 C11 1.385(5)
C10 H10 0.9500
C11 C12 1.376(5)
C11 H11 0.9500
C12 C13 1.389(4)
C12 Cl1 1.742(3)
C13 C14 1.379(4)
C13 H13 0.9500
C14 N1 1.418(4)
N1 S1 1.670(2)
N2 H2A 0.8800
N2 H2B 0.8800
O1 S1 1.423(2)
O2 S1 1.429(2)
