#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:58:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180325 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/39/7153902.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_7153902
loop_
_publ_author_name
'Gao, Zhenzhen'
'Zhang, Lei'
'Sun, Zhanhu'
'Yu, Hao'
'Xiao, Yumei'
'Guo, Hongchao'
_publ_section_title
;
 DABCO-catalyzed [3 + 2] annulation of sulfamate-derived cyclic imines
 with isocyanoacetates: synthesis of sulfamate-fused 2-imidazoline.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5691
_journal_page_last               5697
_journal_paper_doi               10.1039/c4ob00840e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C11 H10 N2 O5 S'
_chemical_formula_sum            'C11 H10 N2 O5 S'
_chemical_formula_weight         282.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.820(11)
_cell_angle_beta                 72.410(9)
_cell_angle_gamma                88.450(12)
_cell_formula_units_Z            2
_cell_length_a                   6.894(2)
_cell_length_b                   9.539(3)
_cell_length_c                   9.718(3)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.16
_cell_volume                     601.2(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7606
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0425
_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)+(0.0438P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2666
_reflns_number_total             2739
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00840e2.cif
_cod_data_source_block           sa2894
_cod_depositor_comments          'Adding full bibliography for 7153902.cif.'
_cod_original_cell_volume        601.3(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153902
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S -0.38667(6) 0.26331(4) 0.84277(4) 0.02816(14) Uani 1 1 d .
O1 O -0.29950(18) 0.37047(13) 0.91943(13) 0.0322(3) Uani 1 1 d .
O2 O -0.44679(18) 0.34104(14) 0.72616(15) 0.0368(3) Uani 1 1 d .
O3 O -0.52505(19) 0.17246(14) 0.95752(14) 0.0393(3) Uani 1 1 d .
O4 O 0.2287(3) -0.03129(14) 0.53098(16) 0.0524(4) Uani 1 1 d .
O5 O 0.33393(19) 0.19146(13) 0.42816(13) 0.0338(3) Uani 1 1 d .
N1 N -0.1861(2) 0.17528(13) 0.77148(14) 0.0234(3) Uani 1 1 d .
N2 N 0.0866(2) 0.05428(15) 0.80846(15) 0.0305(3) Uani 1 1 d .
C1 C -0.1264(2) 0.45360(17) 0.82641(18) 0.0271(3) Uani 1 1 d .
C2 C -0.1020(3) 0.58407(19) 0.8648(2) 0.0357(4) Uani 1 1 d .
H2 H -0.1961 0.6139 0.9481 0.043 Uiso 1 1 calc R
C3 C 0.0626(3) 0.67016(18) 0.7792(2) 0.0386(4) Uani 1 1 d .
H3 H 0.0823 0.7601 0.8037 0.046 Uiso 1 1 calc R
C4 C 0.1988(3) 0.62595(18) 0.6580(2) 0.0363(4) Uani 1 1 d .
H4 H 0.3103 0.6861 0.5989 0.044 Uiso 1 1 calc R
C5 C 0.1726(3) 0.49429(17) 0.62306(19) 0.0296(4) Uani 1 1 d .
H5 H 0.2673 0.4645 0.5400 0.036 Uiso 1 1 calc R
C6 C 0.0091(2) 0.40426(16) 0.70785(17) 0.0238(3) Uani 1 1 d .
C7 C -0.0126(2) 0.26139(15) 0.66507(16) 0.0221(3) Uani 1 1 d .
H7 H -0.0272 0.2736 0.5646 0.027 Uiso 1 1 calc R
C8 C 0.1664(2) 0.15993(16) 0.67559(17) 0.0244(3) Uani 1 1 d .
H8 H 0.2801 0.2160 0.6863 0.029 Uiso 1 1 calc R
C9 C -0.1038(3) 0.07086(17) 0.85745(18) 0.0287(3) Uani 1 1 d .
H9 H -0.1855 0.0169 0.9458 0.034 Uiso 1 1 calc R
C10 C 0.2438(2) 0.09092(17) 0.53957(18) 0.0277(3) Uani 1 1 d .
C11 C 0.4085(3) 0.1497(2) 0.2849(2) 0.0406(4) Uani 1 1 d .
H11A H 0.4686 0.2328 0.2122 0.061 Uiso 1 1 calc R
H11B H 0.2953 0.1109 0.2601 0.061 Uiso 1 1 calc R
H11C H 0.5119 0.0773 0.2852 0.061 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
O3 S1 O2 121.46(8)
O3 S1 O1 105.61(8)
O2 S1 O1 109.02(8)
O3 S1 N1 109.39(8)
O2 S1 N1 107.46(7)
O1 S1 N1 102.26(7)
C1 O1 S1 114.87(10)
C10 O5 C11 117.10(14)
C9 N1 C7 107.26(12)
C9 N1 S1 122.06(11)
C7 N1 S1 115.75(10)
C9 N2 C8 107.94(13)
C2 C1 C6 122.84(16)
C2 C1 O1 115.48(15)
C6 C1 O1 121.67(14)
C1 C2 C3 118.47(17)
C1 C2 H2 120.8
C3 C2 H2 120.8
C4 C3 C2 120.39(16)
C4 C3 H3 119.8
C2 C3 H3 119.8
C5 C4 C3 120.03(17)
C5 C4 H4 120.0
C3 C4 H4 120.0
C4 C5 C6 121.06(17)
C4 C5 H5 119.5
C6 C5 H5 119.5
C1 C6 C5 117.18(15)
C1 C6 C7 123.81(14)
C5 C6 C7 119.01(14)
N1 C7 C6 112.22(12)
N1 C7 C8 99.80(11)
C6 C7 C8 113.23(12)
N1 C7 H7 110.4
C6 C7 H7 110.4
C8 C7 H7 110.4
N2 C8 C10 112.00(13)
N2 C8 C7 106.57(12)
C10 C8 C7 110.78(12)
N2 C8 H8 109.1
C10 C8 H8 109.1
C7 C8 H8 109.1
N2 C9 N1 115.45(14)
N2 C9 H9 122.3
N1 C9 H9 122.3
O4 C10 O5 124.90(16)
O4 C10 C8 127.12(16)
O5 C10 C8 107.98(13)
O5 C11 H11A 109.5
O5 C11 H11B 109.5
H11A C11 H11B 109.5
O5 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4135(13)
S1 O2 1.4160(13)
S1 O1 1.5836(13)
S1 N1 1.6250(14)
O1 C1 1.429(2)
O4 C10 1.192(2)
O5 C10 1.331(2)
O5 C11 1.447(2)
N1 C9 1.415(2)
N1 C7 1.4864(19)
N2 C9 1.269(2)
N2 C8 1.473(2)
C1 C2 1.384(2)
C1 C6 1.386(2)
C2 C3 1.385(3)
C2 H2 0.9500
C3 C4 1.383(3)
C3 H3 0.9500
C4 C5 1.382(2)
C4 H4 0.9500
C5 C6 1.397(2)
C5 H5 0.9500
C6 C7 1.511(2)
C7 C8 1.565(2)
C7 H7 1.0000
C8 C10 1.516(2)
C8 H8 1.0000
C9 H9 0.9500
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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 O1 C1 167.85(11)
O2 S1 O1 C1 -60.12(13)
N1 S1 O1 C1 53.43(12)
O3 S1 N1 C9 -37.08(14)
O2 S1 N1 C9 -170.77(12)
O1 S1 N1 C9 74.53(13)
O3 S1 N1 C7 -170.77(10)
O2 S1 N1 C7 55.54(12)
O1 S1 N1 C7 -59.16(11)
S1 O1 C1 C2 152.68(13)
S1 O1 C1 C6 -28.62(19)
C6 C1 C2 C3 1.4(3)
O1 C1 C2 C3 -179.93(15)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -0.9(3)
C3 C4 C5 C6 0.4(3)
C2 C1 C6 C5 -1.9(2)
O1 C1 C6 C5 179.51(14)
C2 C1 C6 C7 179.07(15)
O1 C1 C6 C7 0.5(2)
C4 C5 C6 C1 1.0(2)
C4 C5 C6 C7 -179.94(15)
C9 N1 C7 C6 -103.58(14)
S1 N1 C7 C6 36.51(15)
C9 N1 C7 C8 16.61(14)
S1 N1 C7 C8 156.70(10)
C1 C6 C7 N1 -4.6(2)
C5 C6 C7 N1 176.35(13)
C1 C6 C7 C8 -116.68(16)
C5 C6 C7 C8 64.30(18)
C9 N2 C8 C10 -113.22(16)
C9 N2 C8 C7 8.07(17)
N1 C7 C8 N2 -14.99(14)
C6 C7 C8 N2 104.47(14)
N1 C7 C8 C10 107.09(13)
C6 C7 C8 C10 -133.46(14)
C8 N2 C9 N1 3.3(2)
C7 N1 C9 N2 -13.93(19)
S1 N1 C9 N2 -150.94(13)
C11 O5 C10 O4 3.7(3)
C11 O5 C10 C8 -176.33(14)
N2 C8 C10 O4 7.1(2)
C7 C8 C10 O4 -111.8(2)
N2 C8 C10 O5 -172.90(13)
C7 C8 C10 O5 68.26(16)
