#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/19/2201964.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_2201964
loop_
_publ_author_name
'Shi, Bojie'
'Chen, Ruyu'
'Huang, You'
_publ_section_title
;
 Diethyl [(6-chlorobenzothiazol-2-yl)amino]thiophosphate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o870
_journal_page_last               o872
_journal_paper_doi               10.1107/S1600536803008237
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C11 H14 Cl1 N2 O2 P1 S2'
_chemical_formula_moiety         'C11 H14 Cl1 N2 O2 P1 S2'
_chemical_formula_sum            'C11 H14 Cl N2 O2 P S2'
_chemical_formula_weight         336.78
_chemical_melting_point          134
_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                78.311(6)
_cell_angle_beta                 70.600(6)
_cell_angle_gamma                77.163(6)
_cell_formula_units_Z            2
_cell_length_a                   7.605(3)
_cell_length_b                   10.288(4)
_cell_length_c                   10.568(4)
_cell_measurement_reflns_used    749
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.88
_cell_volume                     752.9(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4506
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.401
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0465P)²+0.5081P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                2289
_reflns_number_total             3051
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6062.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C11 H14 Cl  N2 O2 P  S2'
_cod_database_code               2201964
_cod_database_fobs_code          2201964
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
Cl1 1.08352(11) 0.39873(10) 0.67323(10) 0.0723(3) Uani d . 1 . . Cl
S1 0.16674(12) 0.04667(8) 1.24178(10) 0.0654(3) Uani d . 1 . . S
S2 0.43263(10) 0.21408(7) 1.00051(8) 0.0471(2) Uani d . 1 . . S
O2 -0.1518(3) 0.1477(2) 1.1279(3) 0.0701(7) Uani d U 1 . . O
N1 0.2657(3) 0.4508(2) 0.9345(2) 0.0374(5) Uani d . 1 . . N
H1 0.1798 0.5198 0.9280 0.045 Uiso calc R 1 . . H
N2 0.0508(3) 0.3201(2) 1.0821(2) 0.0416(5) Uani d . 1 . . N
C1 0.8396(4) 0.4198(3) 0.7500(3) 0.0463(7) Uani d . 1 . . C
C2 0.7300(4) 0.5429(3) 0.7241(3) 0.0481(7) Uani d . 1 . . C
H2A 0.7868 0.6134 0.6672 0.058 Uiso calc R 1 . . H
C3 0.5358(4) 0.5610(3) 0.7829(3) 0.0444(6) Uani d . 1 . . C
H3 0.4608 0.6436 0.7670 0.053 Uiso calc R 1 . . H
C4 0.4558(4) 0.4534(2) 0.8658(2) 0.0352(5) Uani d . 1 . . C
C5 0.5680(4) 0.3310(2) 0.8909(3) 0.0389(6) Uani d . 1 . . C
C6 0.7628(4) 0.3127(3) 0.8334(3) 0.0465(7) Uani d . 1 . . C
H6 0.8384 0.2309 0.8507 0.056 Uiso calc R 1 . . H
C7 0.2237(4) 0.3340(2) 1.0121(2) 0.0357(6) Uani d . 1 . . C
C10 -0.2034(6) 0.0163(4) 1.1551(5) 0.0852(12) Uani d U 1 . . C
H10A -0.0913 -0.0512 1.1534 0.102 Uiso calc R 1 . . H
H10B -0.2504 0.0058 1.0836 0.102 Uiso calc R 1 . . H
C11 -0.3449(7) -0.0078(6) 1.2834(6) 0.125(2) Uani d U 1 . . C
H11A -0.2916 -0.0143 1.3555 0.188 Uiso calc R 1 . . H
H11B -0.3879 -0.0904 1.2892 0.188 Uiso calc R 1 . . H
H11C -0.4496 0.0653 1.2912 0.188 Uiso calc R 1 . . H
P1 -0.01728(10) 0.19160(7) 1.19238(8) 0.0450(2) Uani d . 1 . . P
O1 -0.1606(4) 0.2647(2) 1.3113(2) 0.0857(9) Uani d U 1 . . O
C9 -0.3680(6) 0.2947(5) 1.5277(4) 0.0920(14) Uani d U 1 . . C
H9A -0.3791 0.3907 1.5039 0.138 Uiso calc R 1 . . H
H9B -0.3836 0.2712 1.6230 0.138 Uiso calc R 1 . . H
H9C -0.4639 0.2643 1.5062 0.138 Uiso calc R 1 . . H
C8 -0.1815(6) 0.2306(5) 1.4515(3) 0.0821(12) Uani d U 1 . . C
H8A -0.0839 0.2611 1.4727 0.099 Uiso calc R 1 . . H
H8B -0.1686 0.1337 1.4763 0.099 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 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'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
C5 S2 C7 90.80(12) y
C10 O2 P1 125.2(2) ?
C7 N1 C4 116.2(2) y
C7 N1 H1 121.9 ?
C4 N1 H1 121.9 ?
C7 N2 P1 126.75(18) y
C6 C1 C2 122.3(3) ?
C6 C1 Cl1 118.5(2) ?
C2 C1 Cl1 119.2(2) ?
C1 C2 C3 120.0(3) ?
C1 C2 H2A 120.0 ?
C3 C2 H2A 120.0 ?
C4 C3 C2 118.4(3) ?
C4 C3 H3 120.8 ?
C2 C3 H3 120.8 ?
C3 C4 C5 120.7(2) ?
C3 C4 N1 127.5(2) ?
C5 C4 N1 111.8(2) y
C4 C5 C6 121.1(2) ?
C4 C5 S2 111.4(2) y
C6 C5 S2 127.5(2) y
C1 C6 C5 117.5(3) ?
C1 C6 H6 121.3 ?
C5 C6 H6 121.3 ?
N2 C7 N1 121.7(2) y
N2 C7 S2 128.52(19) y
N1 C7 S2 109.82(18) y
O2 C10 C11 113.5(4) ?
O2 C10 H10A 108.9 ?
C11 C10 H10A 108.9 ?
O2 C10 H10B 108.9 ?
C11 C10 H10B 108.9 ?
H10A C10 H10B 107.7 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
O1 P1 O2 102.66(16) y
O1 P1 N2 100.67(13) y
O2 P1 N2 100.77(12) y
O1 P1 S1 115.64(10) y
O2 P1 S1 114.28(10) y
N2 P1 S1 120.19(9) y
C8 O1 P1 128.1(2) ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
O1 C8 C9 109.0(3) ?
O1 C8 H8A 109.9 ?
C9 C8 H8A 109.9 ?
O1 C8 H8B 109.9 ?
C9 C8 H8B 109.9 ?
H8A C8 H8B 108.3 ?
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
Cl1 C1 . 1.744(3) y
S1 P1 . 1.9228(11) y
S2 C5 . 1.744(3) y
S2 C7 . 1.767(3) y
O2 C10 . 1.439(4) ?
O2 P1 . 1.583(2) y
N1 C7 . 1.348(3) y
N1 C4 . 1.389(3) y
N1 H1 . 0.8600 y
N2 C7 . 1.300(3) y
N2 P1 . 1.629(2) y
C1 C6 . 1.372(4) ?
C1 C2 . 1.383(4) ?
C2 C3 . 1.385(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.384(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(3) y
C5 C6 . 1.387(4) ?
C6 H6 . 0.9300 ?
C10 C11 . 1.439(6) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
P1 O1 . 1.563(2) y
O1 C8 . 1.414(4) ?
C9 C8 . 1.461(6) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 N2 2_567 0.86 2.14 2.996(3) 175
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131733
