#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/15/7151522.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151522
loop_
_publ_author_name
'Heaney, Frances'
'Fenlon, Julie'
'O'Mahony, Colm'
'McArdle, Patrick'
'Cunningham, Desmond'
_publ_section_title
;
 Alpha-oximono-esters as precursors to heterocycles--generation of
 oxazinone N-oxides and cycloaddition to alkene dipolarophiles.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4302
_journal_page_last               4316
_journal_paper_doi               10.1039/b307077h
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C15 H19 N O5 S'
_chemical_formula_weight         325.37
_chemical_name_systematic
;
?
;
_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                   8.3850(10)
_cell_length_b                   11.2710(10)
_cell_length_c                   16.603(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     1569.1(3)
_computing_cell_refinement       'XDS (W.Kabsch, 2000)'
_computing_data_collection       'Marresearch MarControl software'
_computing_data_reduction        'XDS (W.Kabsch, 2000)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Marresearch image plate'
_diffrn_measurement_method       '180 mm image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6779
_diffrn_reflns_theta_full        21.17
_diffrn_reflns_theta_max         21.17
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.859
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0256
_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)+(0.0579P)²+0.4149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0680
_reflns_number_gt                1641
_reflns_number_total             1683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b307077h.txt
_cod_data_source_block           jf1
_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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7151522
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22893(7) 0.42943(5) 0.54172(3) 0.0346(2) Uani 1 1 d . . .
O1 O 0.13093(17) 0.38186(13) 0.69023(10) 0.0350(4) Uani 1 1 d . . .
O2 O 0.3597(2) 0.07251(16) 0.75564(10) 0.0479(5) Uani 1 1 d . . .
O3 O 0.2107(2) 0.31120(14) 0.51157(9) 0.0469(5) Uani 1 1 d . . .
O4 O 0.3490(2) 0.50510(15) 0.50738(10) 0.0492(5) Uani 1 1 d . . .
O5 O 0.5693(2) 0.17629(17) 0.78673(13) 0.0660(6) Uani 1 1 d . . .
N1 N 0.1731(2) 0.27582(15) 0.73660(11) 0.0325(5) Uani 1 1 d . . .
C2A C 0.3467(3) 0.29109(19) 0.74975(14) 0.0326(6) Uani 1 1 d . . .
C1 C 0.2685(3) 0.4250(2) 0.64853(12) 0.0315(5) Uani 1 1 d . . .
H1 H 0.2913 0.5058 0.6672 0.041 Uiso 1 1 calc R . .
C2 C 0.4078(3) 0.3459(2) 0.67052(14) 0.0338(6) Uani 1 1 d . . .
H2A H 0.5046 0.3913 0.6788 0.044 Uiso 1 1 calc R . .
H2B H 0.4265 0.2857 0.6298 0.044 Uiso 1 1 calc R . .
C3 C 0.4316(3) 0.1757(2) 0.76630(15) 0.0413(6) Uani 1 1 d . . .
C4 C 0.1887(3) 0.0645(2) 0.73694(15) 0.0385(6) Uani 1 1 d . . .
H4 H 0.1288 0.0626 0.7876 0.046 Uiso 1 1 calc R . .
C5 C 0.1336(3) 0.1698(2) 0.68822(15) 0.0353(6) Uani 1 1 d . . .
H5 H 0.1896 0.1723 0.6364 0.046 Uiso 1 1 calc R . .
C6 C 0.0424(3) 0.5010(2) 0.53716(14) 0.0324(6) Uani 1 1 d . . .
C7 C 0.0351(3) 0.6224(2) 0.54684(16) 0.0403(6) Uani 1 1 d . . .
H7 H 0.1278 0.6665 0.5540 0.052 Uiso 1 1 calc R . .
C8 C -0.1117(3) 0.6771(2) 0.54572(17) 0.0525(7) Uani 1 1 d . . .
H8 H -0.1185 0.7591 0.5513 0.068 Uiso 1 1 calc R . .
C9 C -0.2475(3) 0.6114(3) 0.53651(15) 0.0528(7) Uani 1 1 d . . .
H9 H -0.3463 0.6489 0.5366 0.069 Uiso 1 1 calc R . .
C10 C -0.2395(3) 0.4904(2) 0.52718(15) 0.0495(7) Uani 1 1 d . . .
H10 H -0.3326 0.4465 0.5209 0.064 Uiso 1 1 calc R . .
C11 C -0.0944(3) 0.4344(2) 0.52719(14) 0.0400(6) Uani 1 1 d . . .
H11 H -0.0881 0.3526 0.5206 0.052 Uiso 1 1 calc R . .
C12 C 0.3708(3) 0.3768(2) 0.82013(15) 0.0437(6) Uani 1 1 d . . .
H12A H 0.3231 0.4519 0.8073 0.061 Uiso 1 1 calc R . .
H12B H 0.4828 0.3874 0.8296 0.061 Uiso 1 1 calc R . .
H12C H 0.3215 0.3448 0.8676 0.061 Uiso 1 1 calc R . .
C13 C 0.1692(3) -0.0528(2) 0.69547(17) 0.0514(7) Uani 1 1 d . . .
H13A H 0.2256 -0.0515 0.6452 0.072 Uiso 1 1 calc R . .
H13B H 0.0580 -0.0672 0.6857 0.072 Uiso 1 1 calc R . .
H13C H 0.2115 -0.1146 0.7290 0.072 Uiso 1 1 calc R . .
C14 C -0.0447(3) 0.1653(3) 0.67489(18) 0.0531(7) Uani 1 1 d . . .
H14A H -0.0976 0.1531 0.7255 0.074 Uiso 1 1 calc R . .
H14B H -0.0699 0.1012 0.6390 0.074 Uiso 1 1 calc R . .
H14C H -0.0798 0.2389 0.6517 0.074 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 119.24(11) . . ?
O3 S1 C6 108.45(11) . . ?
O4 S1 C6 109.45(11) . . ?
O3 S1 C1 109.74(10) . . ?
O4 S1 C1 106.09(10) . . ?
C6 S1 C1 102.59(10) . . ?
C1 O1 N1 109.71(15) . . ?
C3 O2 C4 121.8(2) . . ?
O1 N1 C5 108.68(16) . . ?
O1 N1 C2A 102.70(15) . . ?
C5 N1 C2A 113.21(18) . . ?
N1 C2A C3 112.97(19) . . ?
N1 C2A C12 108.37(19) . . ?
C3 C2A C12 110.1(2) . . ?
N1 C2A C2 104.30(18) . . ?
C3 C2A C2 110.2(2) . . ?
C12 C2A C2 110.82(18) . . ?
O1 C1 C2 107.73(16) . . ?
O1 C1 S1 109.67(14) . . ?
C2 C1 S1 113.24(15) . . ?
C1 C2 C2A 100.71(17) . . ?
O5 C3 O2 118.7(2) . . ?
O5 C3 C2A 120.0(2) . . ?
O2 C3 C2A 121.3(2) . . ?
O2 C4 C13 104.9(2) . . ?
O2 C4 C5 111.3(2) . . ?
C13 C4 C5 114.4(2) . . ?
N1 C5 C4 106.04(18) . . ?
N1 C5 C14 109.1(2) . . ?
C4 C5 C14 110.8(2) . . ?
C7 C6 C11 121.1(2) . . ?
C7 C6 S1 119.26(19) . . ?
C11 C6 S1 119.55(17) . . ?
C8 C7 C6 118.8(2) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C10 120.7(3) . . ?
C11 C10 C9 120.0(3) . . ?
C10 C11 C6 119.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4316(17) . ?
S1 O4 1.4375(18) . ?
S1 C6 1.762(2) . ?
S1 C1 1.805(2) . ?
O1 C1 1.431(3) . ?
O1 N1 1.465(2) . ?
O2 C3 1.322(3) . ?
O2 C4 1.470(3) . ?
O5 C3 1.204(3) . ?
N1 C5 1.478(3) . ?
N1 C2A 1.482(3) . ?
C2A C3 1.508(4) . ?
C2A C12 1.529(4) . ?
C2A C2 1.541(3) . ?
C1 C2 1.514(3) . ?
C4 C13 1.499(4) . ?
C4 C5 1.509(3) . ?
C5 C14 1.512(3) . ?
C6 C7 1.378(3) . ?
C6 C11 1.381(3) . ?
C7 C8 1.378(4) . ?
C8 C9 1.367(4) . ?
C9 C10 1.374(4) . ?
C10 C11 1.371(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189012
