#------------------------------------------------------------------------------
#$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/02/2200203.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_2200203
loop_
_publ_author_name
'Mori, Akira'
'Kubo, Kanji'
' Yin, Bing Zhu'
'Takeshita, Hitoshi'
_publ_section_title
18-Isopropyl-15-(4-nitrophenyl)-5,8,11-trioxa-2,14-dithiabicyclo[14.4.1]henicosa-1(20),16,18-trien-21-one
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o129
_journal_page_last               o130
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C25 H31 N O6 S2'
_chemical_formula_sum            'C25 H31 N O6 S2'
_chemical_formula_weight         505.63
_chemical_name_systematic
;
 ?
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 94.882(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6630(10)
_cell_length_b                   18.862(2)
_cell_length_c                   11.3630(10)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.0
_cell_measurement_theta_min      10.1
_cell_volume                     2490.6(4)
_computing_cell_refinement       ' CAD-4 Software'
_computing_data_collection       ' CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        ' MolEN (Fair, 1990)'
_computing_molecular_graphics    'Xtal_GX (Hall & du Boulay, 1995)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full .000
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Enraf-Nonius FR590'
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .037
_diffrn_reflns_av_sigmaI/netI    .1419
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5321
_diffrn_reflns_theta_full        .50
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.63
_diffrn_standards_decay_%        .6
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .255
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  .982
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         .288
_refine_diff_density_min         -.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          .194
_refine_ls_R_factor_gt           .055
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.8224P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .167
_reflns_number_gt                2259
_reflns_number_total             5059
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ob6022.cif
_[local]_cod_data_source_block   1
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        2490.6(3)
_cod_database_code               2200203
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_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 .81595(9) -.01427(6) .56115(10) .0506(3) Uani d . 1 . . S
S2 .46212(9) .22020(6) .32535(11) .0579(3) Uani d . 1 . . S
O1 .6073(2) .17902(16) .5094(3) .0653(9) Uani d . 1 . . O
O2 .6767(3) -.08465(17) .3318(3) .0685(9) Uani d . 1 . . O
O3 .4360(4) -.0311(2) .2020(3) .1099(14) Uani d . 1 . . O
O4 .3702(3) .11006(19) .1300(3) .0876(11) Uani d . 1 . . O
O5 1.0530(3) .2891(2) .9126(4) .1081(14) Uani d . 1 . . O
O6 1.1901(3) .2278(2) .8541(3) .1036(14) Uani d . 1 . . O
N1 1.0883(4) .2428(2) .8531(3) .0656(11) Uani d . 1 . . N
C1 .6497(3) .1583(2) .4195(4) .0456(10) Uani d . 1 . . C
C2 .7467(3) .10843(19) .4312(3) .0408(9) Uani d . 1 . . C
C3 .8217(3) .0921(2) .3509(4) .0486(10) Uani d . 1 . . C
H3 .8797 .0613 .3797 .058 Uiso calc R 1 . . H
C4 .8300(3) .1124(2) .2318(4) .0482(10) Uani d . 1 . . C
C5 .7444(4) .1476(2) .1657(4) .0561(12) Uani d . 1 . . C
H5 .7591 .1557 .0877 .067 Uiso calc R 1 . . H
C6 .6376(4) .1735(2) .1966(4) .0562(12) Uani d . 1 . . C
H6 .5888 .1894 .1331 .067 Uiso calc R 1 . . H
C7 .5938(3) .1792(2) .3032(4) .0452(10) Uani d . 1 . . C
C8 .9397(4) .0905(2) .1787(4) .0593(12) Uani d . 1 . . C
H8 1.0019 .0978 .2412 .071 Uiso calc R 1 . . H
C9 .9719(4) .1331(3) .0762(4) .0781(16) Uani d . 1 . . C
H9A 1.0433 .1158 .0510 .117 Uiso calc R 1 . . H
H9B .9805 .1819 .0989 .117 Uiso calc R 1 . . H
H9C .9128 .1289 .0124 .117 Uiso calc R 1 . . H
C10 .9374(4) .0110(2) .1542(4) .0735(14) Uani d . 1 . . C
H10A .9181 -.0139 .2234 .110 Uiso calc R 1 . . H
H10B 1.0118 -.0041 .1337 .110 Uiso calc R 1 . . H
H10C .8809 .0010 .0899 .110 Uiso calc R 1 . . H
C11 .7674(3) .07791(19) .5566(3) .0418(9) Uani d . 1 . . C
H11 .6939 .0796 .5924 .050 Uiso calc R 1 . . H
C12 .6801(4) -.0610(2) .5373(4) .0629(13) Uani d . 1 . . C
H12A .6947 -.1111 .5499 .076 Uiso calc R 1 . . H
H12B .6309 -.0455 .5970 .076 Uiso calc R 1 . . H
C13 .6148(4) -.0520(2) .4183(4) .0626(13) Uani d . 1 . . C
H13A .5393 -.0735 .4186 .075 Uiso calc R 1 . . H
H13B .6048 -.0020 .4005 .075 Uiso calc R 1 . . H
C14 .6350(5) -.0687(3) .2141(4) .0869(17) Uani d . 1 . . C
H14A .6825 -.0934 .1613 .104 Uiso calc R 1 . . H
H14B .6448 -.0183 .2014 .104 Uiso calc R 1 . . H
C15 .5119(5) -.0872(3) .1798(5) .0970(19) Uani d . 1 . . C
H15A .5029 -.0989 .0964 .116 Uiso calc R 1 . . H
H15B .4914 -.1288 .2237 .116 Uiso calc R 1 . . H
C16 .3625(5) -.0142(3) .1077(5) .0846(16) Uani d . 1 . . C
H16A .3088 -.0530 .0920 .101 Uiso calc R 1 . . H
H16B .4057 -.0086 .0391 .101 Uiso calc R 1 . . H
C17 .2976(4) .0509(3) .1246(5) .0799(15) Uani d . 1 . . C
H17A .2386 .0566 .0597 .096 Uiso calc R 1 . . H
H17B .2598 .0475 .1972 .096 Uiso calc R 1 . . H
C18 .3107(4) .1729(3) .1419(5) .0912(18) Uani d . 1 . . C
H18A .2554 .1667 .2001 .109 Uiso calc R 1 . . H
H18B .2685 .1846 .0671 .109 Uiso calc R 1 . . H
C19 .3905(4) .2333(2) .1792(4) .0663(13) Uani d . 1 . . C
H19A .3468 .2771 .1782 .080 Uiso calc R 1 . . H
H19B .4480 .2380 .1228 .080 Uiso calc R 1 . . H
C20 .8527(3) .1218(2) .6332(3) .0425(10) Uani d . 1 . . C
C21 .9691(3) .1202(2) .6194(4) .0502(11) Uani d . 1 . . C
H21 .9961 .0922 .5603 .060 Uiso calc R 1 . . H
C22 1.0461(4) .1593(2) .6917(4) .0549(11) Uani d . 1 . . C
H22 1.1245 .1569 .6826 .066 Uiso calc R 1 . . H
C23 1.0067(4) .2015(2) .7762(4) .0484(10) Uani d . 1 . . C
C24 .8917(4) .2062(2) .7908(4) .0550(11) Uani d . 1 . . C
H24 .8656 .2362 .8478 .066 Uiso calc R 1 . . H
C25 .8148(4) .1660(2) .7196(4) .0528(11) Uani d . 1 . . C
H25 .7366 .1685 .7297 .063 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 .0535(6) .0444(6) .0535(7) .0040(5) .0024(5) .0071(6)
S2 .0490(7) .0513(7) .0724(8) .0109(5) -.0010(6) .0080(6)
O1 .068(2) .077(2) .052(2) .0287(17) .0085(16) -.0043(17)
O2 .067(2) .078(2) .059(2) .0078(17) -.0008(17) -.0060(18)
O3 .143(3) .095(3) .080(3) .056(3) -.055(2) -.032(2)
O4 .070(2) .065(2) .126(3) .010(2) -.003(2) -.012(2)
O5 .112(3) .103(3) .105(3) .000(3) -.012(2) -.057(3)
O6 .065(2) .142(4) .102(3) -.021(2) -.006(2) -.033(3)
N1 .078(3) .065(3) .051(2) -.015(2) -.009(2) -.010(2)
C1 .043(2) .041(2) .052(3) -.0034(19) -.001(2) -.007(2)
C2 .039(2) .036(2) .047(2) .0004(18) -.0003(19) .0020(19)
C3 .048(2) .047(3) .051(3) .003(2) .009(2) .003(2)
C4 .055(3) .047(3) .044(3) .004(2) .008(2) .005(2)
C5 .063(3) .067(3) .039(2) -.002(2) .011(2) .003(2)
C6 .056(3) .060(3) .051(3) .002(2) -.003(2) .016(2)
C7 .037(2) .040(2) .057(3) .0014(18) -.005(2) .008(2)
C8 .064(3) .066(3) .049(3) .012(2) .011(2) .005(2)
C9 .081(4) .072(4) .085(4) .000(3) .031(3) .008(3)
C10 .086(4) .062(3) .075(3) .016(3) .020(3) -.003(3)
C11 .045(2) .037(2) .044(2) .0070(18) .0069(18) .0063(19)
C12 .068(3) .055(3) .067(3) -.011(2) .015(3) .006(2)
C13 .057(3) .061(3) .071(3) -.005(2) .008(3) -.005(3)
C14 .103(4) .092(4) .064(4) -.009(3) -.005(3) .000(3)
C15 .104(5) .079(4) .100(5) .019(4) -.037(4) -.031(3)
C16 .097(4) .075(4) .077(4) .002(3) -.021(3) -.003(3)
C17 .079(4) .081(4) .076(4) .003(3) -.016(3) .004(3)
C18 .074(4) .085(4) .109(5) .012(3) -.024(3) -.007(4)
C19 .057(3) .059(3) .080(3) .015(2) -.013(2) .017(3)
C20 .051(2) .040(2) .037(2) .0063(19) .0042(19) .005(2)
C21 .050(3) .051(3) .050(3) .004(2) .010(2) .001(2)
C22 .043(2) .066(3) .055(3) -.005(2) .003(2) .002(2)
C23 .059(3) .043(2) .042(3) .001(2) .001(2) .003(2)
C24 .063(3) .059(3) .043(3) .009(2) .003(2) -.008(2)
C25 .046(2) .060(3) .052(3) .007(2) .003(2) .002(2)
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 C12 . 1.813(4) ?
S1 C11 . 1.828(4) ?
S2 C7 . 1.756(4) yes
S2 C19 . 1.811(4) ?
O1 C1 . 1.236(4) yes
O2 C13 . 1.409(5) ?
O2 C14 . 1.417(5) ?
O3 C16 . 1.352(5) ?
O3 C15 . 1.416(6) ?
O4 C18 . 1.386(6) ?
O4 C17 . 1.399(6) ?
O5 N1 . 1.198(5) ?
O6 N1 . 1.219(5) ?
N1 C23 . 1.462(5) ?
C1 C2 . 1.469(5) yes
C1 C7 . 1.476(5) yes
C2 C3 . 1.352(5) yes
C2 C11 . 1.537(5) ?
C3 C4 . 1.417(5) yes
C4 C5 . 1.369(6) yes
C4 C8 . 1.517(5) ?
C5 C6 . 1.410(6) yes
C6 C7 . 1.359(6) yes
C8 C9 . 1.489(6) ?
C8 C10 . 1.525(6) ?
C11 C20 . 1.512(5) ?
C12 C13 . 1.504(6) ?
C14 C15 . 1.497(7) ?
C16 C17 . 1.464(7) ?
C18 C19 . 1.509(7) ?
C20 C21 . 1.379(5) ?
C20 C25 . 1.389(5) ?
C21 C22 . 1.379(6) ?
C22 C23 . 1.356(6) ?
C23 C24 . 1.368(6) ?
C24 C25 . 1.383(6) ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
C12 S1 C11 101.1(2)
C7 S2 C19 105.6(2)
C13 O2 C14 114.2(4)
C16 O3 C15 113.5(4)
C18 O4 C17 112.3(4)
O5 N1 O6 123.0(4)
O5 N1 C23 119.3(4)
O6 N1 C23 117.7(4)
O1 C1 C2 119.1(4)
O1 C1 C7 118.6(4)
C2 C1 C7 122.0(4)
C3 C2 C1 128.5(4)
C3 C2 C11 118.8(3)
C1 C2 C11 112.5(3)
C2 C3 C4 133.1(4)
C5 C4 C3 123.3(4)
C5 C4 C8 120.9(4)
C3 C4 C8 115.8(4)
C4 C5 C6 130.6(4)
C7 C6 C5 131.0(4)
C6 C7 C1 127.3(4)
C6 C7 S2 124.2(3)
C1 C7 S2 108.3(3)
C9 C8 C4 116.3(4)
C9 C8 C10 112.8(4)
C4 C8 C10 109.7(4)
C20 C11 C2 111.8(3)
C20 C11 S1 108.5(3)
C2 C11 S1 114.0(3)
C13 C12 S1 116.7(3)
O2 C13 C12 109.1(4)
O2 C14 C15 116.1(5)
O3 C15 C14 112.3(5)
O3 C16 C17 113.2(4)
O4 C17 C16 110.9(5)
O4 C18 C19 111.8(4)
C18 C19 S2 112.3(3)
C21 C20 C25 118.0(4)
C21 C20 C11 121.9(4)
C25 C20 C11 120.1(4)
C22 C21 C20 121.2(4)
C23 C22 C21 119.5(4)
C22 C23 C24 121.3(4)
C22 C23 N1 119.5(4)
C24 C23 N1 119.2(4)
C23 C24 C25 119.1(4)
C24 C25 C20 120.9(4)
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
O1 C1 C2 C3 -163.2(4) ?
C7 C1 C2 C3 23.0(6) ?
O1 C1 C2 C11 10.8(5) ?
C7 C1 C2 C11 -163.0(3) ?
C1 C2 C3 C4 -4.1(7) ?
C11 C2 C3 C4 -177.8(4) ?
C2 C3 C4 C5 -11.2(7) ?
C2 C3 C4 C8 170.7(4) ?
C3 C4 C5 C6 3.1(8) ?
C8 C4 C5 C6 -179.0(4) ?
C4 C5 C6 C7 9.2(8) ?
C5 C6 C7 C1 -.3(8) ?
C5 C6 C7 S2 174.4(4) ?
O1 C1 C7 C6 166.7(4) ?
C2 C1 C7 C6 -19.4(6) ?
O1 C1 C7 S2 -8.6(5) ?
C2 C1 C7 S2 165.3(3) ?
C19 S2 C7 C6 11.9(4) ?
C19 S2 C7 C1 -172.5(3) ?
C5 C4 C8 C9 25.1(6) ?
C3 C4 C8 C9 -156.8(4) yes
C5 C4 C8 C10 -104.5(5) ?
C3 C4 C8 C10 73.6(5) yes
C3 C2 C11 C20 83.1(4) ?
C1 C2 C11 C20 -91.5(4) ?
C3 C2 C11 S1 -40.4(4) ?
C1 C2 C11 S1 144.9(3) ?
C12 S1 C11 C20 151.2(3) ?
C12 S1 C11 C2 -83.5(3) yes
C11 S1 C12 C13 66.4(4) yes
C14 O2 C13 C12 -169.0(4) yes
S1 C12 C13 O2 67.5(4) yes
C13 O2 C14 C15 -57.9(6) yes
C16 O3 C15 C14 128.6(5) yes
O2 C14 C15 O3 89.5(6) yes
C15 O3 C16 C17 -170.5(5) yes
C18 O4 C17 C16 177.9(5) yes
O3 C16 C17 O4 67.5(6) yes
C17 O4 C18 C19 165.1(4) yes
O4 C18 C19 S2 -64.9(6) yes
C7 S2 C19 C18 93.3(4) yes
C2 C11 C20 C21 -74.2(5) yes
S1 C11 C20 C21 52.4(4) ?
C2 C11 C20 C25 105.2(4) ?
S1 C11 C20 C25 -128.3(3) ?
C25 C20 C21 C22 2.1(6) ?
C11 C20 C21 C22 -178.5(4) ?
C20 C21 C22 C23 -1.5(6) ?
C21 C22 C23 C24 -.3(6) ?
C21 C22 C23 N1 179.8(4) ?
O5 N1 C23 C22 166.6(4) ?
O6 N1 C23 C22 -13.9(6) ?
O5 N1 C23 C24 -13.2(6) ?
O6 N1 C23 C24 166.3(4) ?
C22 C23 C24 C25 1.5(6) ?
N1 C23 C24 C25 -178.7(4) ?
C23 C24 C25 C20 -.8(6) ?
C21 C20 C25 C24 -.9(6) ?
C11 C20 C25 C24 179.7(4) ?