#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:28:27 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178951 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/80/4118012.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_4118012
loop_
_publ_author_name
'Kyle L. Kimmel'
'Jimmie D. Weaver'
'Melissa Lee'
'Jonathan A. Ellman'
_publ_section_title
;
 Catalytic Enantioselective Protonation of Nitronates Utilizing an
 Organocatalyst Chiral Only at Sulfur
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9058
_journal_page_last               9061
_journal_paper_doi               10.1021/ja3026196
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C10 H15 N O6'
_chemical_formula_weight         245.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.536(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8901(7)
_cell_length_b                   11.4722(11)
_cell_length_c                   12.9352(12)
_cell_measurement_reflns_used    8520
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.42
_cell_volume                     1170.43(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9004
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  0.9248
_exptl_absorpt_correction_T_min  0.7616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       blade
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                3465
_reflns_number_total             3480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3026196_si_001.cif
_cod_data_source_block           ellm07
_cod_database_code               4118012
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O1 O -0.22091(14) 0.44568(11) 0.69846(9) 0.0330(3) Uani 1 1 d .
O1' O 0.46633(18) 0.55637(15) 0.03550(11) 0.0540(4) Uani 1 1 d .
O2 O 0.05298(13) 0.45283(10) 0.70258(8) 0.0282(2) Uani 1 1 d .
O2' O 0.19557(15) 0.53750(12) 0.05010(10) 0.0391(3) Uani 1 1 d .
O3 O 0.31108(13) 0.20695(10) 0.65992(8) 0.0270(2) Uani 1 1 d .
O3' O -0.03384(14) 0.31264(12) -0.07934(8) 0.0333(3) Uani 1 1 d .
O4 O 0.39739(12) 0.36892(11) 0.59002(8) 0.0289(3) Uani 1 1 d .
O4' O -0.12605(13) 0.36580(12) 0.07056(7) 0.0291(3) Uani 1 1 d .
O5 O 0.21281(12) 0.48369(10) 0.47944(8) 0.0261(2) Uani 1 1 d .
O5' O 0.06130(12) 0.37600(11) 0.21996(7) 0.0268(2) Uani 1 1 d .
O6 O -0.05484(12) 0.43661(9) 0.45949(7) 0.0221(2) Uani 1 1 d .
O6' O 0.33234(13) 0.34190(13) 0.20645(8) 0.0360(3) Uani 1 1 d .
N1 N -0.08264(15) 0.39878(12) 0.69859(8) 0.0217(3) Uani 1 1 d .
N1' N 0.33068(18) 0.51108(14) 0.01167(10) 0.0336(3) Uani 1 1 d .
C1 C -0.23159(18) 0.20889(16) 0.72479(11) 0.0253(3) Uani 1 1 d .
H1A H -0.2535 0.2298 0.7950 0.038 Uiso 1 1 calc R
H1B H -0.2195 0.1258 0.7198 0.038 Uiso 1 1 calc R
H1C H -0.3243 0.2340 0.6807 0.038 Uiso 1 1 calc R
C1' C 0.4784(2) 0.4164(2) -0.13368(13) 0.0425(5) Uani 1 1 d .
H1'A H 0.4875 0.4918 -0.1651 0.064 Uiso 1 1 calc R
H1'B H 0.4671 0.3580 -0.1866 0.064 Uiso 1 1 calc R
H1'C H 0.5784 0.4011 -0.0919 0.064 Uiso 1 1 calc R
C2 C -0.06974(17) 0.26719(13) 0.69146(10) 0.0200(3) Uani 1 1 d .
H2A H 0.0232 0.2413 0.7377 0.024 Uiso 1 1 calc R
C2' C 0.3237(2) 0.41351(17) -0.06619(11) 0.0316(4) Uani 1 1 d .
H2'A H 0.2226 0.4245 -0.1108 0.038 Uiso 1 1 calc R
C3 C -0.02792(16) 0.23214(13) 0.58088(10) 0.0190(3) Uani 1 1 d .
H3A H -0.1271 0.2487 0.5374 0.023 Uiso 1 1 calc R
H3B H -0.0121 0.1483 0.5803 0.023 Uiso 1 1 calc R
C3' C 0.30739(19) 0.29668(16) -0.01027(11) 0.0292(4) Uani 1 1 d .
H3'A H 0.4116 0.2839 0.0296 0.035 Uiso 1 1 calc R
H3'B H 0.3005 0.2361 -0.0625 0.035 Uiso 1 1 calc R
C4 C 0.12587(17) 0.28703(13) 0.52865(10) 0.0183(3) Uani 1 1 d .
C4' C 0.15784(19) 0.27873(15) 0.06319(11) 0.0245(3) Uani 1 1 d .
C5 C 0.28228(17) 0.28379(14) 0.59914(10) 0.0201(3) Uani 1 1 d .
C5' C -0.00629(19) 0.32024(15) 0.01176(11) 0.0239(3) Uani 1 1 d .
C6 C 0.38218(17) 0.46784(14) 0.52293(11) 0.0233(3) Uani 1 1 d .
C6' C -0.11268(18) 0.37981(16) 0.18110(10) 0.0260(3) Uani 1 1 d .
C7 C 0.08524(16) 0.40804(13) 0.48877(10) 0.0181(3) Uani 1 1 d .
C7' C 0.19321(19) 0.33650(15) 0.16725(11) 0.0260(3) Uani 1 1 d .
C8 C 0.16409(18) 0.21062(14) 0.43294(11) 0.0236(3) Uani 1 1 d .
H8A H 0.2541 0.2455 0.3951 0.035 Uiso 1 1 calc R
H8B H 0.0642 0.2051 0.3892 0.035 Uiso 1 1 calc R
H8C H 0.1976 0.1341 0.4554 0.035 Uiso 1 1 calc R
C8' C 0.1429(2) 0.14645(16) 0.08574(14) 0.0350(4) Uani 1 1 d .
H8'A H 0.0552 0.1336 0.1345 0.053 Uiso 1 1 calc R
H8'B H 0.2489 0.1181 0.1140 0.053 Uiso 1 1 calc R
H8'C H 0.1155 0.1057 0.0227 0.053 Uiso 1 1 calc R
C9 C 0.50267(18) 0.45328(16) 0.43564(12) 0.0296(3) Uani 1 1 d .
H9A H 0.4680 0.3879 0.3938 0.044 Uiso 1 1 calc R
H9B H 0.6151 0.4401 0.4634 0.044 Uiso 1 1 calc R
H9C H 0.5017 0.5226 0.3940 0.044 Uiso 1 1 calc R
C9' C -0.2124(2) 0.28485(18) 0.23166(12) 0.0329(4) Uani 1 1 d .
H9'A H -0.1662 0.2104 0.2137 0.049 Uiso 1 1 calc R
H9'B H -0.3287 0.2890 0.2082 0.049 Uiso 1 1 calc R
H9'C H -0.2059 0.2946 0.3054 0.049 Uiso 1 1 calc R
C10' C -0.1757(2) 0.50035(17) 0.20431(12) 0.0340(4) Uani 1 1 d .
H10A H -0.1068 0.5567 0.1702 0.051 Uiso 1 1 calc R
H10B H -0.1694 0.5135 0.2776 0.051 Uiso 1 1 calc R
H10C H -0.2912 0.5078 0.1800 0.051 Uiso 1 1 calc R
C10 C 0.4165(2) 0.57354(16) 0.58944(13) 0.0310(4) Uani 1 1 d .
H10D H 0.3313 0.5795 0.6408 0.047 Uiso 1 1 calc R
H10E H 0.4141 0.6422 0.5470 0.047 Uiso 1 1 calc R
H10F H 0.5261 0.5663 0.6229 0.047 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 O4 C6 125.78(10)
C5' O4' C6' 125.11(12)
C7 O5 C6 124.95(11)
C7' O5' C6' 125.14(11)
O1 N1 O2 123.59(14)
O1 N1 C2 120.14(13)
O2 N1 C2 116.26(12)
O1' N1' O2' 123.90(15)
O1' N1' C2' 120.05(14)
O2' N1' C2' 116.00(14)
C1 C2 N1 111.35(12)
C1 C2 C3 110.77(12)
N1 C2 C3 109.58(11)
N1' C2' C1' 110.65(14)
N1' C2' C3' 109.69(12)
C1' C2' C3' 111.69(15)
C2 C3 C4 119.67(12)
C2' C3' C4' 118.81(14)
C7 C4 C5 112.93(12)
C7 C4 C3 111.28(11)
C5 C4 C3 111.39(11)
C7 C4 C8 106.87(11)
C5 C4 C8 107.07(11)
C3 C4 C8 106.93(12)
C5' C4' C7' 112.71(12)
C5' C4' C3' 110.17(12)
C7' C4' C3' 111.14(12)
C5' C4' C8' 108.77(13)
C7' C4' C8' 105.87(13)
C3' C4' C8' 107.97(13)
O3 C5 O4 118.45(12)
O3 C5 C4 123.35(14)
O4 C5 C4 118.15(12)
O3' C5' O4' 118.50(14)
O3' C5' C4' 122.68(13)
O4' C5' C4' 118.82(12)
O4 C6 O5 113.37(11)
O4 C6 C9 108.82(13)
O5 C6 C9 108.52(11)
O4 C6 C10 106.31(12)
O5 C6 C10 105.71(12)
C9 C6 C10 114.21(13)
O4' C6' O5' 112.60(11)
O4' C6' C10' 106.58(13)
O5' C6' C10' 105.90(13)
O4' C6' C9' 109.01(13)
O5' C6' C9' 109.20(13)
C10' C6' C9' 113.58(13)
O6 C7 O5 118.81(13)
O6 C7 C4 122.78(13)
O5 C7 C4 118.26(11)
O6' C7' O5' 118.88(13)
O6' C7' C4' 122.81(14)
O5' C7' C4' 118.16(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2164(17)
O1' N1' 1.2219(19)
O2 N1 1.2366(16)
O2' N1' 1.2263(19)
O3 C5 1.1988(19)
O3' C5' 1.1958(18)
O4 C5 1.3411(18)
O4 C6 1.4316(18)
O4' C5' 1.3353(19)
O4' C6' 1.4399(16)
O5 C7 1.3370(18)
O5 C6 1.4474(16)
O5' C7' 1.3385(18)
O5' C6' 1.4498(17)
O6 C7 1.2041(17)
O6' C7' 1.1984(19)
N1 C2 1.516(2)
N1' C2' 1.506(2)
C1 C2 1.514(2)
C1' C2' 1.520(2)
C2 C3 1.5303(18)
C2' C3' 1.530(2)
C3 C4 1.5393(18)
C3' C4' 1.548(2)
C4 C7 1.512(2)
C4 C5 1.5151(18)
C4 C8 1.5531(19)
C4' C5' 1.517(2)
C4' C7' 1.519(2)
C4' C8' 1.550(2)
C6 C9 1.505(2)
C6 C10 1.507(2)
C6' C10' 1.503(3)
C6' C9' 1.504(3)
