#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/49/1504955.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_1504955
loop_
_publ_author_name
'Reynolds, Troy E.'
'Binkley, Michael S.'
'Scheidt, Karl A.'
_publ_section_title
;
 Highly selective alpha-acylvinyl anion additions to imines.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5227
_journal_page_last               5230
_journal_paper_doi               10.1021/ol802227t
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_sum            'C21 H25 N O2 S'
_chemical_formula_weight         355.48
_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                   6.14540(10)
_cell_length_b                   11.2662(3)
_cell_length_c                   27.9745(7)
_cell_measurement_temperature    100(2)
_cell_volume                     1936.82(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            60097
_diffrn_reflns_theta_full        31.62
_diffrn_reflns_theta_max         31.62
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.183
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         6487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0818P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                5619
_reflns_number_total             6487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802227t_si_002.cif
_cod_data_source_block           s84w_0m
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1504955
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
H11 H 0.107(3) 0.4623(19) 0.8685(6) 0.012(5) Uiso 1 1 d .
S1 S 0.48977(6) 0.34028(3) 0.843487(13) 0.01322(9) Uani 1 1 d .
O1 O -0.2024(2) 0.62048(12) 0.89283(5) 0.0226(3) Uani 1 1 d .
N1 N 0.4309(2) 0.48144(12) 0.85607(5) 0.0127(3) Uani 1 1 d .
O3 O 0.6824(2) 0.30079(12) 0.87167(4) 0.0215(3) Uani 1 1 d .
C5 C 0.2352(2) 0.84607(14) 0.86655(5) 0.0127(3) Uani 1 1 d .
C3 C 0.1789(2) 0.63231(14) 0.88588(6) 0.0117(3) Uani 1 1 d .
C4 C 0.2995(3) 0.71969(14) 0.86767(5) 0.0134(3) Uani 1 1 d .
H4 H 0.4368 0.6992 0.8544 0.016 Uiso 1 1 calc R
C12 C 0.2506(3) 0.45661(13) 0.93729(5) 0.0114(3) Uani 1 1 d .
C18 C 0.5901(3) 0.36055(15) 0.78189(5) 0.0158(3) Uani 1 1 d .
C15 C 0.2616(3) 0.38622(15) 1.03285(6) 0.0171(3) Uani 1 1 d .
H15 H 0.2650 0.3625 1.0654 0.021 Uiso 1 1 calc R
C10 C 0.0281(2) 0.88090(14) 0.85150(5) 0.0142(3) Uani 1 1 d .
H10 H -0.0747 0.8225 0.8420 0.017 Uiso 1 1 calc R
C16 C 0.4324(3) 0.45156(15) 1.01385(6) 0.0175(3) Uani 1 1 d .
H16 H 0.5530 0.4720 1.0334 0.021 Uiso 1 1 calc R
C14 C 0.0864(3) 0.35559(15) 1.00432(6) 0.0171(3) Uani 1 1 d .
H14 H -0.0303 0.3108 1.0174 0.021 Uiso 1 1 calc R
C7 C 0.3278(3) 1.05310(16) 0.87851(6) 0.0174(3) Uani 1 1 d .
H7 H 0.4308 1.1117 0.8877 0.021 Uiso 1 1 calc R
C9 C -0.0289(3) 1.00057(14) 0.85030(5) 0.0157(3) Uani 1 1 d .
H9 H -0.1703 1.0233 0.8401 0.019 Uiso 1 1 calc R
C6 C 0.3846(3) 0.93349(15) 0.87968(6) 0.0159(3) Uani 1 1 d .
H6 H 0.5267 0.9111 0.8895 0.019 Uiso 1 1 calc R
C11 C 0.2365(2) 0.50073(13) 0.88573(5) 0.0109(3) Uani 1 1 d .
C8 C 0.1206(3) 1.08676(15) 0.86398(6) 0.0163(3) Uani 1 1 d .
H8 H 0.0813 1.1683 0.8634 0.020 Uiso 1 1 calc R
C13 C 0.0804(3) 0.39013(14) 0.95661(6) 0.0148(3) Uani 1 1 d .
H13 H -0.0398 0.3684 0.9371 0.018 Uiso 1 1 calc R
C1 C -0.0356(2) 0.65772(14) 0.90987(5) 0.0140(3) Uani 1 1 d .
C19 C 0.3916(3) 0.39080(17) 0.75138(6) 0.0237(4) Uani 1 1 d .
H19A H 0.3298 0.4665 0.7621 0.036 Uiso 1 1 calc R
H19B H 0.2823 0.3280 0.7547 0.036 Uiso 1 1 calc R
H19C H 0.4354 0.3974 0.7178 0.036 Uiso 1 1 calc R
C21 C 0.6830(4) 0.23965(18) 0.76803(7) 0.0283(4) Uani 1 1 d .
H21A H 0.7295 0.2415 0.7345 0.043 Uiso 1 1 calc R
H21B H 0.5711 0.1786 0.7722 0.043 Uiso 1 1 calc R
H21C H 0.8082 0.2213 0.7885 0.043 Uiso 1 1 calc R
C20 C 0.7623(3) 0.45661(17) 0.77955(6) 0.0231(4) Uani 1 1 d .
H20A H 0.8785 0.4386 0.8024 0.035 Uiso 1 1 calc R
H20B H 0.6967 0.5334 0.7875 0.035 Uiso 1 1 calc R
H20C H 0.8230 0.4600 0.7472 0.035 Uiso 1 1 calc R
C17 C 0.4274(3) 0.48717(15) 0.96626(5) 0.0157(3) Uani 1 1 d .
H17 H 0.5442 0.5323 0.9534 0.019 Uiso 1 1 calc R
C2 C -0.0316(3) 0.72271(18) 0.95643(6) 0.0276(4) Uani 1 1 d .
H2A H -0.1741 0.7591 0.9622 0.041 Uiso 1 1 calc R
H2B H 0.0802 0.7847 0.9553 0.041 Uiso 1 1 calc R
H2C H 0.0018 0.6670 0.9823 0.041 Uiso 1 1 calc R
H1 H 0.559(4) 0.528(2) 0.8661(7) 0.027(6) 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 N1 110.19(7)
O3 S1 C18 105.41(7)
N1 S1 C18 98.71(7)
C11 N1 S1 115.85(10)
C10 C5 C6 118.71(15)
C10 C5 C4 121.36(14)
C6 C5 C4 119.91(14)
C4 C3 C1 121.06(15)
C4 C3 C11 126.03(14)
C1 C3 C11 112.91(13)
C3 C4 C5 124.83(14)
C17 C12 C13 119.34(14)
C17 C12 C11 120.74(14)
C13 C12 C11 119.84(14)
C20 C18 C21 111.39(15)
C20 C18 C19 111.98(15)
C21 C18 C19 110.85(14)
C20 C18 S1 111.24(11)
C21 C18 S1 104.58(12)
C19 C18 S1 106.44(11)
C14 C15 C16 119.97(14)
C9 C10 C5 120.54(15)
C15 C16 C17 120.23(15)
C15 C14 C13 120.28(15)
C6 C7 C8 120.05(16)
C8 C9 C10 120.18(15)
C7 C6 C5 120.79(15)
N1 C11 C3 109.50(12)
N1 C11 C12 116.00(13)
C3 C11 C12 109.09(12)
C9 C8 C7 119.71(15)
C14 C13 C12 120.13(15)
O1 C1 C2 121.94(15)
O1 C1 C3 120.11(14)
C2 C1 C3 117.83(14)
C16 C17 C12 120.05(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4904(12)
S1 N1 1.6686(14)
S1 C18 1.8441(16)
O1 C1 1.2059(19)
N1 C11 1.4707(19)
C5 C10 1.397(2)
C5 C6 1.396(2)
C5 C4 1.478(2)
C3 C4 1.333(2)
C3 C1 1.507(2)
C3 C11 1.524(2)
C12 C17 1.399(2)
C12 C13 1.396(2)
C12 C11 1.528(2)
C18 C20 1.515(3)
C18 C21 1.527(2)
C18 C19 1.527(2)
C15 C14 1.384(2)
C15 C16 1.387(2)
C10 C9 1.393(2)
C16 C17 1.391(2)
C14 C13 1.391(2)
C7 C6 1.392(2)
C7 C8 1.389(2)
C9 C8 1.391(2)
C1 C2 1.494(2)
