#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/28/2012850.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_2012850
loop_
_publ_author_name
'Linden, Anthony'
'Majchrzak, Agnieszka'
'Cavegn, Jovita'
'Mloston, Grzegorz'
'Heimgartner, Heinz'
_publ_section_title
;
 Four
 bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)oligosulfanes
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o480
_journal_page_last               o484
_journal_paper_doi               10.1107/S0108270102011319
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C16 H24 Cl2 O2 S2'
_chemical_formula_sum            'C16 H24 Cl2 O2 S2'
_chemical_formula_weight         383.39
_chemical_melting_point          .371E-305
_chemical_name_systematic
;
bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)disulfane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 105.4292(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.73790(10)
_cell_length_b                   26.7454(4)
_cell_length_c                   10.6473(2)
_cell_measurement_reflns_used    103426
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     1849.58(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2002)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR591 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_av_sigmaI/netI    0.047
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            40268
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         5397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.069
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0392P)²+0.5066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.082
_refine_ls_wR_factor_ref         0.093
_reflns_number_gt                3839
_reflns_number_total             5400
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1503.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012850
_cod_database_fobs_code          2012850
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 1.10057(7) 0.069552(19) 0.59120(4) 0.03346(12) Uani d . 1 . . Cl
Cl2 0.78806(6) 0.192378(16) 0.41231(4) 0.02775(11) Uani d . 1 . . Cl
S1 0.64412(6) 0.072255(16) 0.52548(4) 0.02409(10) Uani d . 1 . . S
S2 0.69317(7) 0.086746(16) 0.34955(4) 0.02372(10) Uani d . 1 . . S
O1 1.0234(2) 0.09743(5) 0.97583(12) 0.0380(3) Uani d . 1 . . O
O2 0.2449(2) 0.21167(5) 0.09187(13) 0.0371(3) Uani d . 1 . . O
C1 0.8859(2) 0.08087(6) 0.65477(15) 0.0218(3) Uani d . 1 . . C
C2 0.8876(3) 0.04590(6) 0.77643(16) 0.0241(4) Uani d . 1 . . C
C3 0.9560(3) 0.09207(7) 0.86002(16) 0.0254(4) Uani d . 1 . . C
C4 0.9163(3) 0.12886(7) 0.74607(16) 0.0256(4) Uani d . 1 . . C
C5 1.0378(3) 0.00234(7) 0.80294(19) 0.0363(4) Uani d . 1 . . C
H51 1.1782 0.0149 0.8150 0.054 Uiso calc R 1 . . H
H52 1.0038 -0.0208 0.7290 0.054 Uiso calc R 1 . . H
H53 1.0282 -0.0152 0.8820 0.054 Uiso calc R 1 . . H
C6 0.6747(3) 0.02806(7) 0.78537(18) 0.0320(4) Uani d . 1 . . C
H61 0.6266 0.0009 0.7229 0.048 Uiso calc R 1 . . H
H62 0.5770 0.0560 0.7652 0.048 Uiso calc R 1 . . H
H63 0.6849 0.0160 0.8737 0.048 Uiso calc R 1 . . H
C7 1.0954(3) 0.16412(8) 0.74896(19) 0.0377(5) Uani d . 1 . . C
H71 1.1140 0.1870 0.8231 0.057 Uiso calc R 1 . . H
H72 1.0659 0.1834 0.6678 0.057 Uiso calc R 1 . . H
H73 1.2215 0.1446 0.7578 0.057 Uiso calc R 1 . . H
C8 0.7192(3) 0.15920(7) 0.73639(18) 0.0333(4) Uani d . 1 . . C
H81 0.7369 0.1798 0.8146 0.050 Uiso calc R 1 . . H
H82 0.6030 0.1363 0.7291 0.050 Uiso calc R 1 . . H
H83 0.6919 0.1808 0.6593 0.050 Uiso calc R 1 . . H
C9 0.6083(2) 0.15057(6) 0.30954(15) 0.0213(3) Uani d . 1 . . C
C10 0.5727(3) 0.16323(6) 0.15825(16) 0.0245(4) Uani d . 1 . . C
C11 0.3665(3) 0.18532(6) 0.16538(17) 0.0251(4) Uani d . 1 . . C
C12 0.3766(2) 0.16529(6) 0.30114(16) 0.0227(3) Uani d . 1 . . C
C13 0.7134(3) 0.20109(7) 0.11823(19) 0.0341(4) Uani d . 1 . . C
H131 0.6476 0.2134 0.0303 0.051 Uiso calc R 1 . . H
H132 0.8445 0.1851 0.1191 0.051 Uiso calc R 1 . . H
H133 0.7385 0.2292 0.1795 0.051 Uiso calc R 1 . . H
C14 0.5470(3) 0.11729(7) 0.06844(17) 0.0324(4) Uani d . 1 . . C
H141 0.4941 0.1279 -0.0224 0.049 Uiso calc R 1 . . H
H142 0.4500 0.0938 0.0907 0.049 Uiso calc R 1 . . H
H143 0.6807 0.1009 0.0798 0.049 Uiso calc R 1 . . H
C15 0.3348(3) 0.20333(7) 0.39731(19) 0.0317(4) Uani d . 1 . . C
H151 0.4348 0.2307 0.4082 0.047 Uiso calc R 1 . . H
H152 0.3473 0.1871 0.4816 0.047 Uiso calc R 1 . . H
H153 0.1953 0.2167 0.3641 0.047 Uiso calc R 1 . . H
C16 0.2302(3) 0.12054(7) 0.29045(17) 0.0273(4) Uani d . 1 . . C
H161 0.2555 0.1040 0.3754 0.041 Uiso calc R 1 . . H
H162 0.2544 0.0968 0.2260 0.041 Uiso calc R 1 . . H
H163 0.0874 0.1323 0.2632 0.041 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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
Cl Cl 0.1484 0.1585
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
S S 0.1246 0.1234
; International Tables for Crystallography (1992).
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
C1 S1 S2 109.71(6) yes
C9 S2 S1 106.17(6) yes
C2 C1 C4 90.28(12) yes
C4 C1 Cl1 112.62(11) ?
C2 C1 Cl1 112.22(11) ?
C4 C1 S1 120.07(11) ?
C2 C1 S1 110.29(11) ?
Cl1 C1 S1 109.91(8) ?
C5 C2 C3 115.52(15) ?
C5 C2 C6 109.66(15) ?
C3 C2 C6 110.98(14) ?
C5 C2 C1 117.46(14) ?
C1 C2 C3 86.26(12) yes
C6 C2 C1 115.24(14) ?
O1 C3 C2 132.01(16) ?
O1 C3 C4 132.43(17) ?
C2 C3 C4 95.53(13) yes
C7 C4 C3 114.26(15) ?
C7 C4 C8 109.89(16) ?
C3 C4 C8 111.04(14) ?
C7 C4 C1 118.92(15) ?
C1 C4 C3 86.12(12) yes
C8 C4 C1 114.65(14) ?
C2 C5 H51 109.5 ?
C2 C5 H52 109.5 ?
H51 C5 H52 109.5 ?
C2 C5 H53 109.5 ?
H51 C5 H53 109.5 ?
H52 C5 H53 109.5 ?
C2 C6 H61 109.5 ?
C2 C6 H62 109.5 ?
H61 C6 H62 109.5 ?
C2 C6 H63 109.5 ?
H61 C6 H63 109.5 ?
H62 C6 H63 109.5 ?
C4 C7 H71 109.5 ?
C4 C7 H72 109.5 ?
H71 C7 H72 109.5 ?
C4 C7 H73 109.5 ?
H71 C7 H73 109.5 ?
H72 C7 H73 109.5 ?
C4 C8 H81 109.5 ?
C4 C8 H82 109.5 ?
H81 C8 H82 109.5 ?
C4 C8 H83 109.5 ?
H81 C8 H83 109.5 ?
H82 C8 H83 109.5 ?
C10 C9 C12 90.52(12) yes
C12 C9 Cl2 111.97(11) ?
C10 C9 Cl2 112.25(11) ?
C12 C9 S2 119.33(11) ?
C10 C9 S2 112.87(11) ?
Cl2 C9 S2 108.91(8) ?
C13 C10 C11 113.45(14) ?
C13 C10 C14 109.43(14) ?
C11 C10 C14 112.69(15) ?
C13 C10 C9 118.97(15) ?
C9 C10 C11 85.79(12) yes
C14 C10 C9 114.76(14) ?
O2 C11 C12 132.43(16) ?
O2 C11 C10 131.76(16) ?
C10 C11 C12 95.69(13) yes
C15 C12 C11 115.66(14) ?
C15 C12 C16 109.92(14) ?
C11 C12 C16 109.72(14) ?
C15 C12 C9 118.86(14) ?
C9 C12 C11 86.33(12) yes
C16 C12 C9 114.39(14) ?
C10 C13 H131 109.5 ?
C10 C13 H132 109.5 ?
H131 C13 H132 109.5 ?
C10 C13 H133 109.5 ?
H131 C13 H133 109.5 ?
H132 C13 H133 109.5 ?
C10 C14 H141 109.5 ?
C10 C14 H142 109.5 ?
H141 C14 H142 109.5 ?
C10 C14 H143 109.5 ?
H141 C14 H143 109.5 ?
H142 C14 H143 109.5 ?
C12 C15 H151 109.5 ?
C12 C15 H152 109.5 ?
H151 C15 H152 109.5 ?
C12 C15 H153 109.5 ?
H151 C15 H153 109.5 ?
H152 C15 H153 109.5 ?
C12 C16 H161 109.5 ?
C12 C16 H162 109.5 ?
H161 C16 H162 109.5 ?
C12 C16 H163 109.5 ?
H161 C16 H163 109.5 ?
H162 C16 H163 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
Cl1 C1 . 1.7786(17) yes
Cl2 C9 . 1.7915(17) yes
S1 C1 . 1.8462(16) yes
S1 S2 . 2.0243(6) yes
S2 C9 . 1.8146(17) yes
O1 C3 . 1.204(2) ?
O2 C11 . 1.200(2) ?
C1 C2 . 1.595(2) yes
C1 C4 . 1.590(2) yes
C2 C5 . 1.519(2) ?
C2 C3 . 1.520(2) ?
C2 C6 . 1.539(2) ?
C3 C4 . 1.529(2) ?
C4 C7 . 1.526(3) ?
C4 C8 . 1.536(3) ?
C5 H51 . 0.9800 ?
C5 H52 . 0.9800 ?
C5 H53 . 0.9800 ?
C6 H61 . 0.9800 ?
C6 H62 . 0.9800 ?
C6 H63 . 0.9800 ?
C7 H71 . 0.9800 ?
C7 H72 . 0.9800 ?
C7 H73 . 0.9800 ?
C8 H81 . 0.9800 ?
C8 H82 . 0.9800 ?
C8 H83 . 0.9800 ?
C9 C10 . 1.601(2) yes
C9 C12 . 1.589(2) yes
C10 C13 . 1.523(2) ?
C10 C11 . 1.530(2) ?
C10 C14 . 1.538(2) ?
C11 C12 . 1.526(2) ?
C12 C15 . 1.522(2) ?
C12 C16 . 1.536(2) ?
C13 H131 . 0.9800 ?
C13 H132 . 0.9800 ?
C13 H133 . 0.9800 ?
C14 H141 . 0.9800 ?
C14 H142 . 0.9800 ?
C14 H143 . 0.9800 ?
C15 H151 . 0.9800 ?
C15 H152 . 0.9800 ?
C15 H153 . 0.9800 ?
C16 H161 . 0.9800 ?
C16 H162 . 0.9800 ?
C16 H163 . 0.9800 ?
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
_geom_torsion_publ_flag
C1 S1 S2 C9 -97.90(8) yes
S2 S1 C1 C4 105.37(12) ?
S2 S1 C1 C2 -151.91(9) ?
S2 S1 C1 Cl1 -27.65(10) ?
C4 C1 C2 C5 -126.84(16) ?
Cl1 C1 C2 C5 -12.17(19) ?
S1 C1 C2 C5 110.74(15) ?
C4 C1 C2 C3 -9.93(12) ?
Cl1 C1 C2 C3 104.74(12) ?
S1 C1 C2 C3 -132.34(11) ?
C4 C1 C2 C6 101.53(16) ?
Cl1 C1 C2 C6 -143.80(13) ?
S1 C1 C2 C6 -20.88(18) ?
C5 C2 C3 O1 -49.2(3) ?
C6 C2 C3 O1 76.4(2) ?
C1 C2 C3 O1 -167.9(2) ?
C5 C2 C3 C4 129.12(15) ?
C6 C2 C3 C4 -105.26(15) ?
C1 C2 C3 C4 10.38(13) ?
O1 C3 C4 C7 47.8(3) ?
C2 C3 C4 C7 -130.49(16) ?
O1 C3 C4 C8 -77.2(2) ?
C2 C3 C4 C8 104.53(15) ?
O1 C3 C4 C1 167.9(2) ?
C2 C3 C4 C1 -10.41(13) ?
C2 C1 C4 C7 125.53(16) ?
Cl1 C1 C4 C7 11.22(19) ?
S1 C1 C4 C7 -120.66(15) ?
C2 C1 C4 C3 9.87(12) ?
Cl1 C1 C4 C3 -104.44(12) ?
S1 C1 C4 C3 123.68(13) ?
C2 C1 C4 C8 -101.52(15) ?
Cl1 C1 C4 C8 144.16(13) ?
S1 C1 C4 C8 12.3(2) ?
S1 S2 C9 C12 -58.57(13) ?
S1 S2 C9 C10 -162.95(10) ?
S1 S2 C9 Cl2 71.68(8) ?
C12 C9 C10 C13 124.07(16) ?
Cl2 C9 C10 C13 9.99(19) ?
S2 C9 C10 C13 -113.56(15) ?
C12 C9 C10 C11 9.53(12) ?
Cl2 C9 C10 C11 -104.55(12) ?
S2 C9 C10 C11 131.90(12) ?
C12 C9 C10 C14 -103.55(15) ?
Cl2 C9 C10 C14 142.38(13) ?
S2 C9 C10 C14 18.82(18) ?
C13 C10 C11 O2 46.6(3) ?
C14 C10 C11 O2 -78.5(2) ?
C9 C10 C11 O2 166.4(2) ?
C13 C10 C11 C12 -129.82(15) ?
C14 C10 C11 C12 105.13(15) ?
C9 C10 C11 C12 -9.98(13) ?
O2 C11 C12 C15 -45.9(3) ?
C10 C11 C12 C15 130.42(15) ?
O2 C11 C12 C16 79.1(2) ?
C10 C11 C12 C16 -104.57(15) ?
O2 C11 C12 C9 -166.3(2) ?
C10 C11 C12 C9 10.04(13) ?
C10 C9 C12 C15 -126.95(16) ?
Cl2 C9 C12 C15 -12.62(19) ?
S2 C9 C12 C15 116.25(15) ?
C10 C9 C12 C11 -9.55(12) ?
Cl2 C9 C12 C11 104.77(12) ?
S2 C9 C12 C11 -126.36(12) ?
C10 C9 C12 C16 100.45(15) ?
Cl2 C9 C12 C16 -145.22(12) ?
S2 C9 C12 C16 -16.35(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9211551
