#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:47:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178444 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/65/4026507.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_4026507
loop_
_publ_author_name
'Suneel P. Singh'
'Alex Michaelides'
'A. Rod Merrill'
'Adrian L. Schwan'
_publ_contact_author_address
;department of chemistry 
university of guelph,
Ontario, canada-N1G2W1
;
_publ_contact_author_email       suneelpsingh@gmail.com
_publ_contact_author_fax         1-519-7661499
_publ_contact_author_name        'suneel p singh'
_publ_contact_author_phone       '1-519-8244120 X58198'
_publ_section_title
;
 A Microwave-Assisted Synthesis of (S)-N-Protected Homoserine γ-Lactones
 from l-Aspartic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6825
_journal_page_last               6831
_journal_paper_doi               10.1021/jo2008093
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C10 H10 N2 O6 S'
_chemical_formula_sum            'C10 H10 N2 O6 S'
_chemical_formula_weight         286.27
_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                   7.6599(15)
_cell_length_b                   9.3279(19)
_cell_length_c                   16.515(3)
_cell_measurement_temperature    150(1)
_cell_volume                     1180.0(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      150(1)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4943
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.2043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                1971
_reflns_number_total             2199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2008093_si_002.cif
_cod_data_source_block           k1101
_cod_database_code               4026507
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
S1 S 0.05551(8) 0.40518(6) 0.91281(3) 0.02858(17) Uani 1 1 d
O1 O 0.2270(3) 0.1046(2) 0.78324(12) 0.0439(5) Uani 1 1 d
O2 O 0.5054(3) 0.1600(2) 0.76085(12) 0.0386(5) Uani 1 1 d
O3 O -0.0203(2) 0.39912(19) 0.83402(11) 0.0380(4) Uani 1 1 d
O4 O -0.0389(2) 0.35241(18) 0.98136(10) 0.0344(4) Uani 1 1 d
O5 O 0.2567(3) 0.4484(2) 1.06770(11) 0.0382(5) Uani 1 1 d
O6 O 0.1484(3) 0.6149(2) 1.14315(12) 0.0565(6) Uani 1 1 d
N1 N 0.2389(3) 0.3225(2) 0.90889(13) 0.0315(5) Uani 1 1 d
N2 N 0.1831(3) 0.5641(2) 1.07700(13) 0.0356(5) Uani 1 1 d
C1 C 0.3475(3) 0.1852(3) 0.79198(16) 0.0313(6) Uani 1 1 d
C2 C 0.3493(3) 0.3280(3) 0.83727(14) 0.0274(5) Uani 1 1 d
C3 C 0.5434(4) 0.3522(3) 0.85286(16) 0.0325(6) Uani 1 1 d
C4 C 0.6264(4) 0.2749(3) 0.78207(18) 0.0374(6) Uani 1 1 d
C5 C 0.0952(3) 0.5919(3) 0.93083(14) 0.0280(5) Uani 1 1 d
C6 C 0.1440(3) 0.6518(3) 1.00564(15) 0.0297(6) Uani 1 1 d
C7 C 0.1595(4) 0.7987(3) 1.01477(18) 0.0375(6) Uani 1 1 d
C8 C 0.1307(4) 0.8890(3) 0.94974(19) 0.0414(7) Uani 1 1 d
C9 C 0.0810(4) 0.8314(3) 0.87613(17) 0.0381(6) Uani 1 1 d
C10 C 0.0619(3) 0.6846(3) 0.86678(15) 0.0319(5) Uani 1 1 d
H1 H 0.285(4) 0.302(3) 0.955(2) 0.046(9) Uiso 1 1 d
H2 H 0.307(3) 0.399(3) 0.8000(16) 0.028(7) Uiso 1 1 d
H3A H 0.588(3) 0.304(3) 0.9091(16) 0.032(7) Uiso 1 1 d
H3B H 0.580(3) 0.451(3) 0.8536(14) 0.027(6) Uiso 1 1 d
H4A H 0.741(4) 0.230(3) 0.7956(16) 0.030(7) Uiso 1 1 d
H4B H 0.637(4) 0.338(3) 0.7346(17) 0.036(7) Uiso 1 1 d
H7 H 0.191(4) 0.840(3) 1.068(2) 0.054(9) Uiso 1 1 d
H8 H 0.138(4) 0.991(4) 0.9576(19) 0.056(10) Uiso 1 1 d
H9 H 0.060(3) 0.899(3) 0.8320(15) 0.034(7) Uiso 1 1 d
H10 H 0.028(4) 0.642(3) 0.8169(19) 0.044(8) Uiso 1 1 d
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
O3 S1 O4 120.15(11)
O3 S1 N1 107.50(12)
O4 S1 N1 108.03(11)
O3 S1 C5 105.02(11)
O4 S1 C5 106.78(11)
N1 S1 C5 108.98(11)
C1 O2 C4 110.7(2)
C2 N1 S1 121.69(18)
C2 N1 H1 119(2)
S1 N1 H1 115(2)
O6 N2 O5 123.6(2)
O6 N2 C6 117.3(2)
O5 N2 C6 119.0(2)
O1 C1 O2 122.7(2)
O1 C1 C2 127.8(2)
O2 C1 C2 109.5(2)
N1 C2 C3 115.8(2)
N1 C2 C1 111.2(2)
C3 C2 C1 102.8(2)
N1 C2 H2 110.6(15)
C3 C2 H2 109.3(15)
C1 C2 H2 106.5(16)
C4 C3 C2 102.0(2)
C4 C3 H3A 109.3(14)
C2 C3 H3A 112.9(14)
C4 C3 H3B 110.2(15)
C2 C3 H3B 115.1(16)
H3A C3 H3B 107(2)
O2 C4 C3 105.6(2)
O2 C4 H4A 108.0(16)
C3 C4 H4A 113.3(16)
O2 C4 H4B 107.4(16)
C3 C4 H4B 111.5(16)
H4A C4 H4B 111(2)
C10 C5 C6 118.0(2)
C10 C5 S1 116.56(19)
C6 C5 S1 125.24(19)
C7 C6 C5 120.8(2)
C7 C6 N2 116.6(2)
C5 C6 N2 122.6(2)
C8 C7 C6 120.3(3)
C8 C7 H7 119.8(18)
C6 C7 H7 119.9(18)
C7 C8 C9 119.4(3)
C7 C8 H8 119.2(19)
C9 C8 H8 121.3(19)
C8 C9 C10 120.7(3)
C8 C9 H9 116.9(15)
C10 C9 H9 122.4(15)
C9 C10 C5 120.7(3)
C9 C10 H10 122.5(17)
C5 C10 H10 116.8(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4261(18)
S1 O4 1.4309(17)
S1 N1 1.604(2)
S1 C5 1.793(3)
O1 C1 1.199(3)
O2 C1 1.335(3)
O2 C4 1.459(3)
O5 N2 1.228(3)
O6 N2 1.220(3)
N1 C2 1.455(3)
N1 H1 0.86(3)
N2 C6 1.466(3)
C1 C2 1.527(4)
C2 C3 1.526(4)
C2 H2 0.96(3)
C3 C4 1.514(4)
C3 H3A 1.09(3)
C3 H3B 0.96(3)
C4 H4A 1.00(3)
C4 H4B 0.98(3)
C5 C10 1.390(3)
C5 C6 1.407(3)
C6 C7 1.384(4)
C7 C8 1.382(4)
C7 H7 0.99(3)
C8 C9 1.382(4)
C8 H8 0.96(4)
C9 C10 1.386(4)
C9 H9 0.98(3)
C10 H10 0.95(3)
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
O3 S1 N1 C2 35.4(2)
O4 S1 N1 C2 166.43(19)
C5 S1 N1 C2 -77.9(2)
C4 O2 C1 O1 -179.2(3)
C4 O2 C1 C2 1.3(3)
S1 N1 C2 C3 135.5(2)
S1 N1 C2 C1 -107.7(2)
O1 C1 C2 N1 36.3(4)
O2 C1 C2 N1 -144.2(2)
O1 C1 C2 C3 160.8(3)
O2 C1 C2 C3 -19.7(3)
N1 C2 C3 C4 150.3(2)
C1 C2 C3 C4 28.8(3)
C1 O2 C4 C3 18.0(3)
C2 C3 C4 O2 -29.0(3)
O3 S1 C5 C10 -5.3(2)
O4 S1 C5 C10 -133.93(19)
N1 S1 C5 C10 109.6(2)
O3 S1 C5 C6 169.6(2)
O4 S1 C5 C6 41.0(2)
N1 S1 C5 C6 -75.5(2)
C10 C5 C6 C7 -0.5(4)
S1 C5 C6 C7 -175.3(2)
C10 C5 C6 N2 -179.6(2)
S1 C5 C6 N2 5.5(3)
O6 N2 C6 C7 32.6(3)
O5 N2 C6 C7 -143.4(2)
O6 N2 C6 C5 -148.2(3)
O5 N2 C6 C5 35.8(3)
C5 C6 C7 C8 -1.4(4)
N2 C6 C7 C8 177.8(2)
C6 C7 C8 C9 2.0(4)
C7 C8 C9 C10 -0.8(4)
C8 C9 C10 C5 -1.1(4)
C6 C5 C10 C9 1.7(4)
S1 C5 C10 C9 177.0(2)
