#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010284.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_2010284
loop_
_publ_author_name
'Muskett, F.W.'
'Sawyer, L.'
'Taylor, P.'
'Dawson, I.M.'
'Blake, A.J.'
_publ_section_title
9-(1,3-Dithian-2-yl)-10-oxa-1-azatricyclo[7.4.0.0^3,8^]trideca-3,5,7-trien-2-one
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2003
_journal_page_last               2004
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C15 H17 N1 O2 S2'
_chemical_formula_sum            'C15 H17 N O2 S2'
_chemical_formula_weight         306.42
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 98.997(13)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   12.2411(15)
_cell_length_b                   8.0563(9)
_cell_length_c                   15.354(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293
_cell_measurement_theta_max      32
_cell_measurement_theta_min      30
_cell_volume                     1495.6(3)
_diffrn_measurement_device       'Siemens-Stoe AED-2 four-circle'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2130
_diffrn_reflns_theta_max         22.5
_diffrn_standards_decay_%        0.36
_diffrn_standards_interval_time  120
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  0.622
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type
' empirical (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.303
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1766
_refine_ls_R_factor_obs          0.0350
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 1/[\s^2^(F) + 0.000060F^2^]'
_refine_ls_wR_factor_obs         0.0498
_reflns_number_observed          1744
_reflns_number_total             1913
_reflns_observed_criterion       F~o~>4\s(F~o~)
_[local]_cod_data_source_file    ha1092.cif
_[local]_cod_data_source_block   ha1092a
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_[local]_cod_chemical_formula_sum_orig 'C15 H17 N1 O2 S2'
_cod_original_cell_volume        1495.6(2)
_cod_database_code               2010284
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,1/2-y,1/2+z
-x,-y,-z
-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
N(1) .10402(15) -.0639(2) .28621(12) .0340(11)
C(2) -.00601(19) -.0593(3) .31189(17) .0440(15)
C(3) -.0096(2) -.1888(4) .38304(18) .0516(17)
C(4) .0880(2) -.1679(4) .45593(17) .0505(17)
O(5) .19167(14) -.1768(2) .42223(10) .0398(10)
C(6) .20147(18) -.0593(3) .35495(14) .0329(13)
C(7) .29152(19) -.1184(3) .30553(15) .0353(14)
C(8) .2459(2) -.1561(3) .21934(16) .0384(15)
C(9) .1248(2) -.1238(3) .20782(16) .0365(14)
O(10) .05559(15) -.1469(2) .14251(11) .0524(12)
C(11) .3085(2) -.2214(3) .16014(18) .0519(17)
C(12) .4204(3) -.2447(4) .1889(2) .063(2)
C(13) .4665(2) -.2046(4) .2744(2) .061(2)
C(14) .4030(2) -.1416(3) .33475(18) .0476(17)
S(1') .26498(6) .24926(8) .30941(4) .0431(4)
C(2') .2166(2) .1200(3) .39186(15) .0352(14)
S(3') .30770(7) .12121(9) .49747(5) .0596(5)
C(4') .3015(3) .3420(4) .5208(2) .068(2)
C(5') .3399(3) .4539(4) .4527(2) .065(2)
C(6') .2653(2) .4483(3) .36402(19) .0551(18)
H(11) .27150(4) -.2532(3) .09372(18) .0300000
H(12) .4720(3) -.2946(4) .1443(2) .0300000
H(13) .5542(2) -.2227(4) .2950(2) .0300000
H(14) .4395(2) -.1121(3) .40161(18) .0300000
H(21) -.02143(19) .0622(3) .33708(17) .0400000
H(22) -.06791(19) -.0869(3) .25557(17) .0400000
H(31) -.0069(2) -.3110(4) .35459(18) .0400000
H(32) -.0854(2) -.1749(4) .41014(18) .0400000
H(41) .0859(2) -.2651(4) .50408(17) .0600000
H(42) .0821(2) -.0486(4) .48692(17) .0600000
H(2') .1390(2) .1702(3) .40493(15) .0300000
H(41') .3529(3) .3656(4) .5834(2) .0600000
H(42') .2168(3) .3734(4) .5253(2) .0600000
H(51') .3425(3) .5799(4) .4769(2) .0600000
H(52') .4220(3) .4159(4) .4436(2) .0600000
H(61') .1819(2) .4761(3) .37403(19) .0600000
H(62') .2930(2) .5415(3) .32184(19) .0600000
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(6) . . 1.464(3) yes
N(1) C(9) . . 1.358(3) yes
C(2) N(1) . . 1.462(3) yes
C(3) C(2) . . 1.516(4) no
C(4) C(3) . . 1.513(4) no
C(4) O(5) . . 1.446(3) yes
C(6) O(5) . . 1.420(3) yes
C(6) C(2') . . 1.552(3) yes
C(7) C(6) . . 1.510(3) yes
C(8) C(7) . . 1.387(3) yes
C(8) C(11) . . 1.381(4) no
C(9) C(8) . . 1.488(3) yes
C(9) O(10) . . 1.222(3) yes
C(11) C(12) . . 1.384(4) no
C(12) C(13) . . 1.384(4) no
C(13) C(14) . . 1.395(4) no
C(14) C(7) . . 1.380(4) no
C(2') S(1') . . 1.809(2) yes
C(2') S(3') . . 1.819(3) yes
S(3') C(4') . . 1.819(3) yes
C(4') C(5') . . 1.510(5) no
C(5') C(6') . . 1.518(4) no
C(6') S(1') . . 1.809(3) yes
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
C(2) N(1) C(9) 123.8(2) yes
C(2) N(1) C(6) 119.08(18) yes
C(9) N(1) C(6) 113.78(18) yes
C(3) C(2) N(1) 108.0(2) no
C(4) C(3) C(2) 110.4(2) no
C(3) C(4) O(5) 111.4(2) no
C(4) O(5) C(6) 113.96(18) yes
N(1) C(6) C(7) 101.90(17) no
N(1) C(6) O(5) 110.82(17) yes
N(1) C(6) C(2') 108.91(18) no
C(7) C(6) O(5) 107.85(18) no
C(7) C(6) C(2') 114.98(19) no
O(5) C(6) C(2') 111.94(18) no
C(8) C(7) C(6) 109.4(2) no
C(8) C(7) C(14) 120.7(2) no
C(14) C(7) C(6) 129.9(2) yes
C(9) C(8) C(7) 108.7(2) no
C(9) C(8) C(11) 129.3(2) yes
C(11) C(8) C(7) 122.0(2) no
N(1) C(9) C(8) 106.2(2) no
N(1) C(9) O(10) 125.4(2) no
O(10) C(9) C(8) 128.4(2) no
C(8) C(11) C(12) 117.7(3) no
C(11) C(12) C(13) 120.5(3) no
C(12) C(13) C(14) 121.8(3) no
C(13) C(14) C(7) 117.3(2) no
C(2') S(1') C(6') 99.39(12) yes
S(3') C(2') S(1') 113.50(13) yes
C(6) C(2') S(1') 108.28(16) no
C(2') S(3') C(4') 98.18(13) yes
S(3') C(4') C(5') 114.9(2) no
C(4') C(5') C(6') 113.2(3) no
C(5') C(6') S(1') 113.6(2) no
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
C(2) N(1) C(6) O(5) 48.8(3) no
C(2) N(1) C(6) C(7) 163.32(19) no
C(2) N(1) C(9) C(8) -162.3(2) no
C(2) N(1) C(9) O(10) 16.9(4) no
C(2) N(1) C(6) C(2') -74.8(2) yes
C(6) N(1) C(9) C(8) -3.1(3) no
C(6) N(1) C(9) O(10) 176.1(2) no
C(9) N(1) C(6) O(5) -111.5(2) yes
C(9) N(1) C(6) C(7) 3.1(2) yes
C(9) N(1) C(6) C(2') 125.0(2) yes
C(3) C(2) N(1) C(9) 108.6(3) no
C(8) C(2) N(1) C(6) -49.5(3) no
C(4) C(3) C(2) N(1) 51.2(3) no
C(3) C(4) O(5) C(6) 56.8(3) no
O(5) C(4) C(3) C(2) -56.9(3) no
N(1) C(6) O(5) C(4) -50.2(2) no
N(1) C(6) C(2') S(1') -72.33(19) no
N(1) C(6) C(2') S(3') 162.71(15) yes
O(5) C(6) C(2') S(3') 39.8(2) yes
O(5) C(6) C(2') S(1') 164.77(15) yes
C(7) C(6) O(5) C(4) -160.93(19) no
C(7) C(6) C(2') S(1') 41.3(2) no
C(7) C(6) C(2') S(3') -83.7(2) no
C(2') C(6) O(5) C(4) 71.6(2) no
C(8) C(7) C(6) O(5) 115.0(2) no
C(8) C(7) C(6) C(2') -119.4(2) no
C(14) C(7) C(6) N(1) -179.7(2) no
C(14) C(7) C(6) O(5) -63.0(3) no
C(14) C(7) C(6) C(2') 62.7(3) no
C(7) C(8) C(11) C(12) -1.6(4) no
C(9) C(8) C(7) C(6) 0.1(3) no
C(9) C(8) C(7) C(14) 178.2(2) no
C(9) C(8) C(11) C(12) -177.5(3) no
C(11) C(8) C(7) C(6) -176.6(2) no
C(11) C(8) C(7) C(14) 1.6(4) no
N(1) C(9) C(8) C(7) 1.8(3) no
N(1) C(9) C(8) C(11) 178.2(3) no
O(10) C(9) C(8) C(7) -177.4(3) no
O(10) C(9) C(8) C(11) -1.0(4) no
C(8) C(11) C(12) C(13) 0.5(4) no
C(11) C(12) C(13) C(14) 0.7(5) no
C(12) C(13) C(14) C(7) -0.8(4) no
C(13) C(14) C(7) C(6) 177.5(3) no
C(13) C(14) C(7) C(8) -0.3(4) no
C(6) C(2') S(1') C(6') 175.84(16) no
C(6) C(2') S(3') C(4') -178.06(18) no
S(1') C(2') S(3') C(4') 60.00(16) no
S(3') C(2') S(1') C(6') -60.92(16) no
C(2') S(3') C(4') C(5') -59.2(3) no
S(3') C(4') C(5') C(6') 66.4(3) no
C(4') C(5') C(6') S(1') -65.9(3) no
C(5') C(6') S(1') C(2') 59.5(2) no
_journal_paper_doi 10.1107/S0108270194003343