#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/40/2014042.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_2014042
loop_
_publ_author_name
'Jem-Mau Lo'
'Golam Mostafa'
'Ling-Yin Chang'
'Fen-Ling Liao'
'Tian-Huey Lu'
_publ_section_title
;
 3,3,10,10-Tetramethyl-1,2-dithia-5,8-diazacyclodeca-4,8-diene
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o276
_journal_page_last               o277
_journal_paper_doi               10.1107/S0108270104004688
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H18 N2 S2'
_chemical_formula_moiety         'C10 H18 N2 S2'
_chemical_formula_sum            'C10 H18 N2 S2'
_chemical_formula_weight         230.38
_chemical_melting_point          165
_chemical_name_systematic
;
3,3,10,10-Tetramethyl-1,2-dithia-5,8-diazacyclodeca-4,8-diene
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7393(9)
_cell_length_b                   8.9284(9)
_cell_length_c                   15.9117(17)
_cell_measurement_reflns_used    8043
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.6
_cell_volume                     1241.6(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8043
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_T_max  0.8905
_exptl_absorpt_correction_T_min  0.8068
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.205
_refine_ls_abs_structure_details 'Flack (1983), 1172 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0349
_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)+(0.0315P)²+0.0808P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                2057
_reflns_number_total             2963
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob1167.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2014042
_cod_database_fobs_code          2014042
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
S1 0.29986(8) 0.64572(8) 0.14156(5) 0.04935(19) Uani d . 1 . . S
S2 0.10285(7) 0.54753(8) 0.10449(4) 0.04719(18) Uani d . 1 . . S
C3 0.0667(3) 0.3789(3) 0.17070(15) 0.0410(6) Uani d . 1 . . C
C4 0.1645(3) 0.2562(2) 0.13549(16) 0.0384(6) Uani d . 1 . . C
H4 0.1527 0.2320 0.0790 0.046 Uiso calc R 1 . . H
N5 0.2612(2) 0.1842(2) 0.17723(13) 0.0425(5) Uani d . 1 . . N
C6 0.3609(3) 0.0836(3) 0.13032(18) 0.0519(7) Uani d . 1 . . C
H6A 0.3166 0.0625 0.0757 0.062 Uiso calc R 1 . . H
H6B 0.3721 -0.0102 0.1604 0.062 Uiso calc R 1 . . H
C7 0.5168(3) 0.1580(3) 0.11960(16) 0.0503(7) Uani d . 1 . . C
H7A 0.5612 0.1789 0.1742 0.060 Uiso calc R 1 . . H
H7B 0.5853 0.0916 0.0894 0.060 Uiso calc R 1 . . H
N8 0.4971(2) 0.2973(2) 0.07275(13) 0.0437(5) Uani d . 1 . . N
C9 0.4970(3) 0.4165(3) 0.11454(15) 0.0395(6) Uani d . 1 . . C
H9 0.5201 0.4103 0.1715 0.047 Uiso calc R 1 . . H
C10 0.4620(3) 0.5683(3) 0.07895(15) 0.0401(6) Uani d . 1 . . C
C11 0.0938(3) 0.4080(3) 0.26331(15) 0.0545(7) Uani d . 1 . . C
H11A 0.0285 0.4880 0.2818 0.082 Uiso calc R 1 . . H
H11B 0.1988 0.4356 0.2720 0.082 Uiso calc R 1 . . H
H11C 0.0712 0.3190 0.2948 0.082 Uiso calc R 1 . . H
C12 -0.1026(3) 0.3459(4) 0.1517(2) 0.0666(8) Uani d . 1 . . C
H12A -0.1651 0.4246 0.1744 0.100 Uiso calc R 1 . . H
H12B -0.1310 0.2522 0.1769 0.100 Uiso calc R 1 . . H
H12C -0.1174 0.3405 0.0920 0.100 Uiso calc R 1 . . H
C13 0.5927(3) 0.6772(3) 0.09900(18) 0.0599(8) Uani d . 1 . . C
H13A 0.5697 0.7738 0.0757 0.090 Uiso calc R 1 . . H
H13B 0.6862 0.6402 0.0750 0.090 Uiso calc R 1 . . H
H13C 0.6040 0.6857 0.1588 0.090 Uiso calc R 1 . . H
C14 0.4272(3) 0.5642(3) -0.01436(14) 0.0519(7) Uani d . 1 . . C
H14A 0.4049 0.6637 -0.0338 0.078 Uiso calc R 1 . . H
H14B 0.3403 0.5007 -0.0242 0.078 Uiso calc R 1 . . H
H14C 0.5142 0.5257 -0.0442 0.078 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0535(4) 0.0368(3) 0.0577(4) -0.0054(3) 0.0111(3) -0.0084(3)
S2 0.0402(3) 0.0447(4) 0.0567(4) 0.0059(3) 0.0016(3) 0.0124(3)
C3 0.0366(14) 0.0420(15) 0.0445(14) 0.0014(11) 0.0064(10) 0.0056(11)
C4 0.0376(13) 0.0379(13) 0.0398(13) -0.0067(11) -0.0008(11) 0.0005(12)
N5 0.0426(12) 0.0354(12) 0.0495(12) 0.0011(10) 0.0036(10) 0.0061(10)
C6 0.0574(16) 0.0335(13) 0.0646(18) 0.0066(12) 0.0075(14) 0.0032(13)
C7 0.0503(15) 0.0426(15) 0.0581(17) 0.0139(13) 0.0057(13) 0.0017(15)
N8 0.0427(12) 0.0426(13) 0.0459(12) 0.0035(11) 0.0074(11) 0.0003(11)
C9 0.0322(12) 0.0492(16) 0.0372(13) -0.0004(12) -0.0001(11) 0.0047(13)
C10 0.0370(13) 0.0406(15) 0.0427(13) -0.0024(12) 0.0045(10) 0.0042(12)
C11 0.0613(18) 0.0558(17) 0.0464(15) 0.0055(15) 0.0145(14) 0.0017(13)
C12 0.0355(14) 0.0715(19) 0.093(2) -0.0029(16) 0.0048(16) 0.0128(19)
C13 0.0522(16) 0.0520(18) 0.0756(19) -0.0157(15) 0.0036(17) 0.0046(15)
C14 0.0538(16) 0.0579(18) 0.0440(14) 0.0057(15) 0.0036(12) 0.0094(14)
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
_geom_angle_publ_flag
C10 S1 S2 109.32(8) yes
C3 S2 S1 109.26(8) yes
C4 C3 C11 113.6(2) yes
C4 C3 C12 109.6(2) yes
C11 C3 C12 112.0(2) yes
C4 C3 S2 106.40(15) yes
C11 C3 S2 112.61(19) yes
C12 C3 S2 101.91(17) yes
N5 C4 C3 124.2(2) ?
N5 C4 H4 117.9 ?
C3 C4 H4 117.9 ?
C4 N5 C6 116.6(2) ?
N5 C6 C7 108.9(2) ?
N5 C6 H6A 109.9 ?
C7 C6 H6A 109.9 ?
N5 C6 H6B 109.9 ?
C7 C6 H6B 109.9 ?
H6A C6 H6B 108.3 ?
N8 C7 C6 108.8(2) ?
N8 C7 H7A 109.9 ?
C6 C7 H7A 109.9 ?
N8 C7 H7B 109.9 ?
C6 C7 H7B 109.9 ?
H7A C7 H7B 108.3 ?
C9 N8 C7 116.9(2) ?
N8 C9 C10 124.5(2) ?
N8 C9 H9 117.8 ?
C10 C9 H9 117.8 ?
C9 C10 C14 112.9(2) ?
C9 C10 C13 110.1(2) ?
C14 C10 C13 111.6(2) ?
C9 C10 S1 106.72(16) ?
C14 C10 S1 112.28(17) ?
C13 C10 S1 102.69(18) ?
C3 C11 H11A 109.5 ?
C3 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C3 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C3 C12 H12A 109.5 ?
C3 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C3 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C10 C13 H13A 109.5 ?
C10 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C10 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C10 C14 H14A 109.5 ?
C10 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C10 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
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
S1 C10 . 1.865(2) yes
S1 S2 . 2.0201(10) yes
S2 C3 . 1.865(2) yes
C3 C4 . 1.498(3) yes
C3 C11 . 1.515(3) ?
C3 C12 . 1.539(3) ?
C4 N5 . 1.252(3) yes
C4 H4 . 0.9300 ?
N5 C6 . 1.457(3) yes
C6 C7 . 1.525(3) yes
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 N8 . 1.460(3) yes
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
N8 C9 . 1.255(3) yes
C9 C10 . 1.501(3) yes
C9 H9 . 0.9300 ?
C10 C14 . 1.516(3) ?
C10 C13 . 1.533(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14178378
