#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239478.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_2239478
loop_
_publ_author_name
'Mitchell, Lauren A.'
'Mejía, Michelle L.'
'Keskin, Seyma Gören'
'Holliday, Bradley J.'
_publ_section_title
;
 5-Phenyl-1,2,5-dithiazepane
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o285
_journal_paper_doi               10.1107/S1600536814002207
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H13 N S2'
_chemical_formula_moiety         'C10 H13 N S2'
_chemical_formula_sum            'C10 H13 N S2'
_chemical_formula_weight         211.33
_chemical_name_systematic
;
5-Phenyl-1,2,5-dithiazepane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 120.392(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5760(2)
_cell_length_b                   12.2310(3)
_cell_length_c                   9.9811(2)
_cell_measurement_reflns_used    1974
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.00
_cell_volume                     1008.38(4)
_computing_cell_refinement       'COLLECT (Nonius, 1998)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'SIR97 (Altomare et al., 1999) within WinGX (Farrugia, 2012)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3055
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         4.11
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  .8556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(DENZO and SCALEPACK; Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0266P)²+0.5691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0640
_reflns_number_gt                1675
_reflns_number_total             1763
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5658sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239478
_cod_database_fobs_code          2239478
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
S S1 1.04272(4) 0.28440(3) 0.62971(4) 0.02268(12) Uani d . 1 1
S S2 1.07376(4) 0.34787(3) 0.83210(4) 0.02409(12) Uani d . 1 1
N N1 0.74239(13) 0.43703(9) 0.57782(13) 0.0190(3) Uani d . 1 1
C C1 0.65295(16) 0.42454(11) 0.65031(15) 0.0187(3) Uani d . 1 1
C C2 0.66903(17) 0.49796(12) 0.76593(16) 0.0218(3) Uani d . 1 1
H H2 0.7434 0.5548 0.7965 0.026 Uiso calc R 1 1
C C3 0.57560(17) 0.48654(13) 0.83458(16) 0.0261(3) Uani d . 1 1
H H3 0.5882 0.5360 0.9107 0.031 Uiso calc R 1 1
C C4 0.46349(18) 0.40283(13) 0.79229(17) 0.0282(3) Uani d . 1 1
H H4 0.4006 0.3960 0.8386 0.034 Uiso calc R 1 1
C C5 0.44731(17) 0.32959(13) 0.67931(17) 0.0261(3) Uani d . 1 1
H H5 0.3723 0.2732 0.6495 0.031 Uiso calc R 1 1
C C6 0.54029(17) 0.33875(12) 0.61020(16) 0.0223(3) Uani d . 1 1
H H6 0.5285 0.2877 0.5362 0.027 Uiso calc R 1 1
C C7 0.72559(17) 0.36111(11) 0.45867(16) 0.0217(3) Uani d . 1 1
H H7A 0.7562 0.3982 0.3915 0.026 Uiso calc R 1 1
H H7B 0.6125 0.3407 0.3958 0.026 Uiso calc R 1 1
C C8 0.82641(17) 0.25754(11) 0.52070(17) 0.0224(3) Uani d . 1 1
H H8A 0.8026 0.2096 0.4342 0.027 Uiso calc R 1 1
H H8B 0.7956 0.2197 0.5873 0.027 Uiso calc R 1 1
C C9 0.87194(17) 0.51649(11) 0.63274(17) 0.0231(3) Uani d . 1 1
H H9A 0.8296 0.5868 0.6406 0.028 Uiso calc R 1 1
H H9B 0.9037 0.5236 0.5550 0.028 Uiso calc R 1 1
C C10 1.02434(18) 0.49172(12) 0.78971(17) 0.0259(3) Uani d . 1 1
H H10A 1.0103 0.5229 0.8715 0.031 Uiso calc R 1 1
H H10B 1.1157 0.5283 0.7926 0.031 Uiso calc R 1 1
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'
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
C8 S1 S2 102.27(5)
C10 S2 S1 104.34(5)
C1 N1 C7 121.14(11)
C1 N1 C9 121.04(11)
C7 N1 C9 117.26(11)
N1 C1 C2 121.28(12)
N1 C1 C6 121.45(12)
C2 C1 C6 117.26(13)
C3 C2 C1 120.81(14)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 121.32(14)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 118.41(14)
C5 C4 H4 120.8
C3 C4 H4 120.8
C6 C5 C4 121.30(14)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 120.88(14)
C5 C6 H6 119.6
C1 C6 H6 119.6
N1 C7 C8 114.49(11)
N1 C7 H7A 108.6
C8 C7 H7A 108.6
N1 C7 H7B 108.6
C8 C7 H7B 108.6
H7A C7 H7B 107.6
C7 C8 S1 112.92(10)
C7 C8 H8A 109.0
S1 C8 H8A 109.0
C7 C8 H8B 109.0
S1 C8 H8B 109.0
H8A C8 H8B 107.8
N1 C9 C10 116.32(11)
N1 C9 H9A 108.2
C10 C9 H9A 108.2
N1 C9 H9B 108.2
C10 C9 H9B 108.2
H9A C9 H9B 107.4
C9 C10 S2 115.45(10)
C9 C10 H10A 108.4
S2 C10 H10A 108.4
C9 C10 H10B 108.4
S2 C10 H10B 108.4
H10A C10 H10B 107.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.8171(14)
S1 S2 2.0406(5)
S2 C10 1.8155(15)
N1 C1 1.3811(18)
N1 C7 1.4523(18)
N1 C9 1.4478(18)
C1 C2 1.408(2)
C1 C6 1.410(2)
C2 C3 1.382(2)
C2 H2 0.9300
C3 C4 1.386(2)
C3 H3 0.9300
C4 C5 1.386(2)
C4 H4 0.9300
C5 C6 1.379(2)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.5216(19)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.537(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
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
C8 S1 S2 C10 -83.89(7)
C7 N1 C1 C2 179.96(12)
C9 N1 C1 C2 8.78(19)
C7 N1 C1 C6 -0.92(19)
C9 N1 C1 C6 -172.10(12)
N1 C1 C2 C3 178.13(12)
C6 C1 C2 C3 -1.0(2)
C1 C2 C3 C4 0.0(2)
C2 C3 C4 C5 0.4(2)
C3 C4 C5 C6 0.2(2)
C4 C5 C6 C1 -1.3(2)
N1 C1 C6 C5 -177.53(12)
C2 C1 C6 C5 1.6(2)
C1 N1 C7 C8 -83.69(15)
C9 N1 C7 C8 87.82(15)
N1 C7 C8 S1 -62.44(14)
S2 S1 C8 C7 73.74(10)
C1 N1 C9 C10 69.91(16)
C7 N1 C9 C10 -101.60(14)
N1 C9 C10 S2 32.78(16)
S1 S2 C10 C9 44.11(12)
