#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:30:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180302 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151605.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_7151605
loop_
_publ_author_name
'Scanlan, Eoin M.'
'Slawin, Alexandra M. Z.'
'Walton, John C.'
_publ_section_title
;
 Preparation of beta- and gamma-lactams from carbamoyl radicals derived
 from oxime oxalate amides.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              716
_journal_page_last               724
_journal_paper_doi               10.1039/b315223e
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C20 H24 N2 O5 S'
_chemical_formula_sum            'C20 H24 N2 O5 S'
_chemical_formula_weight         404.47
_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'
_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                 94.949(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9072(13)
_cell_length_b                   18.141(3)
_cell_length_c                   12.9956(19)
_cell_measurement_reflns_used    128
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      168
_cell_measurement_theta_min      12
_cell_volume                     2092.1(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 0.9
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8782
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.708574
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0517P)²+0.4950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                2569
_reflns_number_total             2956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b315223e.txt
_cod_data_source_block           7B
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'MULTISCAN' changed to
'multi-scan' 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_cell_volume        2092.1(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7151605
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_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
N1 N 0.32030(15) 0.36145(7) 0.50242(11) 0.0214(3) Uani 1 1 d . . .
C2 C 0.47675(18) 0.35655(9) 0.47082(13) 0.0218(4) Uani 1 1 d . . .
H2A H 0.5123 0.4063 0.4502 0.026 Uiso 1 1 calc R . .
S3 S 0.45836(5) 0.29538(2) 0.35946(3) 0.02627(16) Uani 1 1 d . . .
C4 C 0.2637(2) 0.32473(10) 0.32353(14) 0.0257(4) Uani 1 1 d . . .
C5 C 0.19819(18) 0.33474(9) 0.42951(13) 0.0224(4) Uani 1 1 d . . .
H5A H 0.1167 0.3728 0.4224 0.027 Uiso 1 1 calc R . .
C6 C 0.28346(18) 0.38909(9) 0.59284(13) 0.0210(4) Uani 1 1 d . . .
O6 O 0.15458(13) 0.39016(7) 0.61902(9) 0.0292(3) Uani 1 1 d . . .
C7 C 0.40885(18) 0.42637(9) 0.66227(13) 0.0209(4) Uani 1 1 d . . .
O7 O 0.47141(13) 0.48114(6) 0.63769(9) 0.0262(3) Uani 1 1 d . . .
O8 O 0.42306(13) 0.39258(6) 0.75455(9) 0.0248(3) Uani 1 1 d . . .
N9 N 0.53859(16) 0.42638(8) 0.82511(11) 0.0254(3) Uani 1 1 d . . .
C10 C 0.52072(19) 0.40260(9) 0.91530(13) 0.0230(4) Uani 1 1 d . . .
H10A H 0.4409 0.3694 0.9257 0.028 Uiso 1 1 calc R . .
C11 C 0.62398(18) 0.42653(9) 1.00351(13) 0.0221(4) Uani 1 1 d . . .
C12 C 0.6073(2) 0.39643(10) 1.10033(14) 0.0274(4) Uani 1 1 d . . .
H12A H 0.5315 0.3605 1.1079 0.033 Uiso 1 1 calc R . .
C13 C 0.7007(2) 0.41863(11) 1.18616(15) 0.0330(5) Uani 1 1 d . . .
H13A H 0.6890 0.3977 1.2520 0.040 Uiso 1 1 calc R . .
C14 C 0.8105(2) 0.47106(12) 1.17526(15) 0.0355(5) Uani 1 1 d . . .
H14A H 0.8740 0.4866 1.2337 0.043 Uiso 1 1 calc R . .
C15 C 0.8280(2) 0.50101(11) 1.07899(15) 0.0350(5) Uani 1 1 d . . .
H15A H 0.9040 0.5369 1.0717 0.042 Uiso 1 1 calc R . .
C16 C 0.7360(2) 0.47913(10) 0.99337(14) 0.0288(4) Uani 1 1 d . . .
H16A H 0.7490 0.4999 0.9276 0.035 Uiso 1 1 calc R . .
C17 C 0.58350(19) 0.32492(9) 0.55478(14) 0.0250(4) Uani 1 1 d . . .
H17A H 0.5546 0.2803 0.5859 0.030 Uiso 1 1 calc R . .
C18 C 0.71548(19) 0.35403(10) 0.58949(14) 0.0273(4) Uani 1 1 d . . .
C19 C 0.8098(2) 0.31889(13) 0.67753(17) 0.0432(5) Uani 1 1 d . . .
H19A H 0.8134 0.3513 0.7380 0.065 Uiso 1 1 calc R . .
H19B H 0.9121 0.3109 0.6576 0.065 Uiso 1 1 calc R . .
H19C H 0.7653 0.2715 0.6945 0.065 Uiso 1 1 calc R . .
C20 C 0.7813(2) 0.42303(11) 0.54789(17) 0.0380(5) Uani 1 1 d . . .
H20A H 0.7102 0.4441 0.4940 0.057 Uiso 1 1 calc R . .
H20B H 0.8761 0.4112 0.5185 0.057 Uiso 1 1 calc R . .
H20C H 0.8006 0.4588 0.6039 0.057 Uiso 1 1 calc R . .
C21 C 0.2591(2) 0.39792(10) 0.26504(15) 0.0304(4) Uani 1 1 d . . .
H21A H 0.3054 0.3916 0.1999 0.046 Uiso 1 1 calc R . .
H21B H 0.3148 0.4354 0.3072 0.046 Uiso 1 1 calc R . .
H21C H 0.1542 0.4137 0.2506 0.046 Uiso 1 1 calc R . .
C22 C 0.1834(2) 0.26501(11) 0.25736(14) 0.0334(5) Uani 1 1 d . . .
H22A H 0.0768 0.2781 0.2433 0.050 Uiso 1 1 calc R . .
H22B H 0.1917 0.2178 0.2942 0.050 Uiso 1 1 calc R . .
H22C H 0.2299 0.2607 0.1920 0.050 Uiso 1 1 calc R . .
C23 C 0.1329(2) 0.26316(10) 0.46732(13) 0.0262(4) Uani 1 1 d . . .
O23 O 0.20454(15) 0.21345(7) 0.50850(10) 0.0336(3) Uani 1 1 d . . .
O24 O -0.01648(14) 0.26260(7) 0.44390(10) 0.0326(3) Uani 1 1 d . . .
C25 C -0.0936(2) 0.19566(11) 0.46838(17) 0.0439(5) Uani 1 1 d . . .
H25A H -0.0588 0.1550 0.4269 0.066 Uiso 1 1 calc R . .
H25B H -0.2024 0.2022 0.4529 0.066 Uiso 1 1 calc R . .
H25C H -0.0719 0.1844 0.5419 0.066 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
C6 N1 C5 117.79(14) . . ?
C6 N1 C2 124.63(13) . . ?
C5 N1 C2 117.58(13) . . ?
N1 C2 C17 111.85(14) . . ?
N1 C2 S3 103.51(10) . . ?
C17 C2 S3 110.71(12) . . ?
C2 S3 C4 92.51(8) . . ?
C22 C4 C21 110.24(15) . . ?
C22 C4 C5 112.94(15) . . ?
C21 C4 C5 110.09(15) . . ?
C22 C4 S3 108.96(13) . . ?
C21 C4 S3 111.28(12) . . ?
C5 C4 S3 103.15(11) . . ?
N1 C5 C23 110.93(14) . . ?
N1 C5 C4 107.34(13) . . ?
C23 C5 C4 111.73(14) . . ?
O6 C6 N1 123.63(15) . . ?
O6 C6 C7 118.85(15) . . ?
N1 C6 C7 117.34(14) . . ?
O7 C7 O8 127.41(15) . . ?
O7 C7 C6 122.84(15) . . ?
O8 C7 C6 109.41(14) . . ?
C7 O8 N9 112.20(12) . . ?
C10 N9 O8 107.47(14) . . ?
N9 C10 C11 119.88(16) . . ?
C12 C11 C16 119.15(16) . . ?
C12 C11 C10 118.69(16) . . ?
C16 C11 C10 122.15(16) . . ?
C11 C12 C13 120.50(18) . . ?
C14 C13 C12 119.80(18) . . ?
C13 C14 C15 119.93(17) . . ?
C16 C15 C14 120.62(18) . . ?
C15 C16 C11 119.98(17) . . ?
C18 C17 C2 125.53(16) . . ?
C17 C18 C19 120.61(17) . . ?
C17 C18 C20 124.69(16) . . ?
C19 C18 C20 114.70(16) . . ?
O23 C23 O24 125.02(16) . . ?
O23 C23 C5 125.49(16) . . ?
O24 C23 C5 109.44(15) . . ?
C23 O24 C25 116.00(15) . . ?
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
N1 C6 1.344(2) . ?
N1 C5 1.462(2) . ?
N1 C2 1.489(2) . ?
C2 C17 1.498(2) . ?
C2 S3 1.8197(17) . ?
S3 C4 1.8350(18) . ?
C4 C22 1.523(2) . ?
C4 C21 1.529(3) . ?
C4 C5 1.552(3) . ?
C5 C23 1.521(2) . ?
C6 O6 1.225(2) . ?
C6 C7 1.531(2) . ?
C7 O7 1.196(2) . ?
C7 O8 1.343(2) . ?
O8 N9 1.4536(18) . ?
N9 C10 1.272(2) . ?
C10 C11 1.472(2) . ?
C11 C12 1.391(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.382(3) . ?
C17 C18 1.332(2) . ?
C18 C19 1.501(3) . ?
C18 C20 1.503(3) . ?
C23 O23 1.203(2) . ?
C23 O24 1.339(2) . ?
O24 C25 1.444(2) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C17 47.3(2) . . . . ?
C5 N1 C2 C17 -133.14(15) . . . . ?
C6 N1 C2 S3 166.52(13) . . . . ?
C5 N1 C2 S3 -13.93(16) . . . . ?
N1 C2 S3 C4 29.75(11) . . . . ?
C17 C2 S3 C4 149.75(13) . . . . ?
C2 S3 C4 C22 -157.73(13) . . . . ?
C2 S3 C4 C21 80.52(13) . . . . ?
C2 S3 C4 C5 -37.49(12) . . . . ?
C6 N1 C5 C23 -71.71(18) . . . . ?
C2 N1 C5 C23 108.71(17) . . . . ?
C6 N1 C5 C4 165.97(14) . . . . ?
C2 N1 C5 C4 -13.61(19) . . . . ?
C22 C4 C5 N1 151.51(15) . . . . ?
C21 C4 C5 N1 -84.79(16) . . . . ?
S3 C4 C5 N1 34.04(15) . . . . ?
C22 C4 C5 C23 29.7(2) . . . . ?
C21 C4 C5 C23 153.39(14) . . . . ?
S3 C4 C5 C23 -87.77(14) . . . . ?
C5 N1 C6 O6 3.2(2) . . . . ?
C2 N1 C6 O6 -177.21(15) . . . . ?
C5 N1 C6 C7 -171.92(14) . . . . ?
C2 N1 C6 C7 7.6(2) . . . . ?
O6 C6 C7 O7 -111.41(19) . . . . ?
N1 C6 C7 O7 64.0(2) . . . . ?
O6 C6 C7 O8 62.40(19) . . . . ?
N1 C6 C7 O8 -122.20(16) . . . . ?
O7 C7 O8 N9 -5.4(2) . . . . ?
C6 C7 O8 N9 -178.83(12) . . . . ?
C7 O8 N9 C10 165.41(14) . . . . ?
O8 N9 C10 C11 178.97(13) . . . . ?
N9 C10 C11 C12 -176.35(16) . . . . ?
N9 C10 C11 C16 4.7(2) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C10 C11 C12 C13 -178.77(15) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
C10 C11 C16 C15 178.54(16) . . . . ?
N1 C2 C17 C18 -130.10(18) . . . . ?
S3 C2 C17 C18 115.03(17) . . . . ?
C2 C17 C18 C19 177.25(17) . . . . ?
C2 C17 C18 C20 -1.6(3) . . . . ?
N1 C5 C23 O23 -39.9(2) . . . . ?
C4 C5 C23 O23 79.8(2) . . . . ?
N1 C5 C23 O24 142.62(14) . . . . ?
C4 C5 C23 O24 -97.65(16) . . . . ?
O23 C23 O24 C25 -1.8(3) . . . . ?
C5 C23 O24 C25 175.74(15) . . . . ?
