#------------------------------------------------------------------------------
#$Date: 2019-11-11 18:14:16 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/54/4035406.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_4035406
loop_
_publ_author_name
'Fernández-Sánchez, Luis'
'Fernández-Salas, José A'
'Maestro, M. Carmen'
'García Ruano, Jose L'
_publ_section_title
;
 Reformatsky Reaction to Alkynyl N- tert-Butanesulfinyl Imines: Lewis Acid
 Controlled Stereodivergent Synthesis of β-Alkynyl-β-Amino Acids.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12903
_journal_page_last               12910
_journal_paper_doi               10.1021/acs.joc.8b01918
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H31 N O3 S Si'
_chemical_formula_weight         345.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7993(4)
_cell_length_b                   16.3444(11)
_cell_length_c                   21.7331(14)
_cell_measurement_reflns_used    4323
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.3248
_cell_measurement_theta_min      2.6628
_cell_volume                     2060.0(2)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10156
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.645
_refine_ls_abs_structure_details
;

Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0647P)²+2.0021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                3500
_reflns_number_total             3745
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01918_si_002.cif
_cod_data_source_block           00544CarmenMaestro
_cod_database_code               4035406
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.3836(7) 0.5745(2) 0.00013(17) 0.0143(7) Uani d . . 1
H H1 0.2744 0.5987 -0.0305 0.017 Uiso calc U R 1
C C2 0.5974(7) 0.5428(2) -0.03392(17) 0.0161(8) Uani d . . 1
H H2A 0.6759 0.5894 -0.054 0.019 Uiso calc U R 1
H H2B 0.7057 0.5189 -0.0036 0.019 Uiso calc U R 1
C C3 0.5412(6) 0.4790(2) -0.08196(17) 0.0162(8) Uani d . . 1
C C4 0.2909(7) 0.4551(2) -0.17146(18) 0.0207(9) Uani d . . 1
C C5 0.1773(8) 0.3786(3) -0.1463(2) 0.0280(10) Uani d . . 1
H H5A 0.2949 0.343 -0.1281 0.042 Uiso calc U R 1
H H5B 0.0992 0.3495 -0.1797 0.042 Uiso calc U R 1
H H5C 0.0644 0.3938 -0.1147 0.042 Uiso calc U R 1
C C6 0.4849(9) 0.4357(3) -0.21537(18) 0.0310(10) Uani d . . 1
H H6A 0.5683 0.4861 -0.2255 0.046 Uiso calc U R 1
H H6B 0.4216 0.4118 -0.2531 0.046 Uiso calc U R 1
H H6C 0.5909 0.3967 -0.196 0.046 Uiso calc U R 1
C C7 0.1129(10) 0.5110(3) -0.2013(2) 0.0393(13) Uani d . . 1
H H7A -0.0058 0.5253 -0.1711 0.059 Uiso calc U R 1
H H7B 0.0412 0.4827 -0.2362 0.059 Uiso calc U R 1
H H7C 0.1886 0.5609 -0.2159 0.059 Uiso calc U R 1
C C8 0.2656(7) 0.5082(2) 0.03348(16) 0.0159(7) Uani d . . 1
C C9 0.1657(7) 0.4532(2) 0.05846(18) 0.0184(8) Uani d . . 1
C C10 -0.2206(9) 0.4307(3) 0.1471(2) 0.0348(11) Uani d . . 1
H H10A -0.1417 0.4726 0.1716 0.052 Uiso calc U R 1
H H10B -0.2984 0.3921 0.1747 0.052 Uiso calc U R 1
H H10C -0.3346 0.4569 0.1203 0.052 Uiso calc U R 1
C C11 0.1888(9) 0.3132(3) 0.1492(2) 0.0408(13) Uani d . . 1
H H11A 0.2993 0.2834 0.1235 0.061 Uiso calc U R 1
H H11B 0.0971 0.2742 0.1732 0.061 Uiso calc U R 1
H H11C 0.2723 0.3497 0.1772 0.061 Uiso calc U R 1
C C12 -0.1527(9) 0.3096(3) 0.0418(2) 0.0289(10) Uani d . . 1
H H12A -0.2414 0.3442 0.0135 0.043 Uiso calc U R 1
H H12B -0.2571 0.2717 0.0629 0.043 Uiso calc U R 1
H H12C -0.0377 0.2785 0.0185 0.043 Uiso calc U R 1
C C13 0.4447(6) 0.7322(2) 0.14240(16) 0.0155(8) Uani d . . 1
C C14 0.5963(7) 0.7937(2) 0.10930(19) 0.0208(9) Uani d . . 1
H H14A 0.6813 0.8263 0.1396 0.031 Uiso calc U R 1
H H14B 0.4999 0.8299 0.0842 0.031 Uiso calc U R 1
H H14C 0.7057 0.7647 0.0828 0.031 Uiso calc U R 1
C C15 0.2781(8) 0.7751(2) 0.18629(19) 0.0248(9) Uani d . . 1
H H15A 0.3655 0.8017 0.2193 0.037 Uiso calc U R 1
H H15B 0.1723 0.7347 0.2041 0.037 Uiso calc U R 1
H H15C 0.1895 0.8164 0.1637 0.037 Uiso calc U R 1
C C16 0.5868(8) 0.6680(3) 0.17591(19) 0.0254(9) Uani d . . 1
H H16A 0.7048 0.6462 0.1481 0.038 Uiso calc U R 1
H H16B 0.4857 0.6234 0.1895 0.038 Uiso calc U R 1
H H16C 0.6613 0.6929 0.2118 0.038 Uiso calc U R 1
N N1 0.4620(5) 0.63971(18) 0.04273(13) 0.0145(7) Uani d . . 1
H H1A 0.6063 0.6561 0.0445 0.017 Uiso calc U R 1
O O1 0.1290(5) 0.74605(18) 0.05382(12) 0.0237(6) Uani d . . 1
O O2 0.3755(5) 0.50692(16) -0.12025(12) 0.0194(6) Uani d . . 1
O O3 0.6319(5) 0.41295(17) -0.08555(14) 0.0267(7) Uani d . . 1
S S1 0.25500(17) 0.67953(5) 0.08701(4) 0.0144(2) Uani d . . 1
Si Si1 -0.0055(2) 0.37476(6) 0.09920(5) 0.0191(3) Uani d . . 1
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'
Si Si 0.0817 0.0704 '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
C8 C1 N1 111.3(3)
C8 C1 C2 111.4(3)
N1 C1 C2 107.2(3)
C3 C2 C1 113.1(3)
O3 C3 O2 125.0(4)
O3 C3 C2 124.7(3)
O2 C3 C2 110.3(3)
O2 C4 C6 110.4(3)
O2 C4 C5 110.1(3)
C6 C4 C5 112.3(3)
O2 C4 C7 101.6(3)
C6 C4 C7 111.2(4)
C5 C4 C7 110.7(4)
C9 C8 C1 177.4(4)
C8 C9 Si1 175.3(4)
C14 C13 C16 111.7(3)
C14 C13 C15 111.0(3)
C16 C13 C15 111.1(3)
C14 C13 S1 110.2(3)
C16 C13 S1 108.2(3)
C15 C13 S1 104.2(3)
C1 N1 S1 114.8(2)
C3 O2 C4 120.4(3)
O1 S1 N1 110.89(15)
O1 S1 C13 105.47(17)
N1 S1 C13 97.43(16)
C9 Si1 C12 108.91(19)
C9 Si1 C11 109.2(2)
C12 Si1 C11 111.3(2)
C9 Si1 C10 106.7(2)
C12 Si1 C10 110.5(2)
C11 Si1 C10 110.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C8 1.472(5)
C1 N1 1.484(5)
C1 C2 1.534(5)
C2 C3 1.510(5)
C3 O3 1.204(4)
C3 O2 1.351(5)
C4 O2 1.482(4)
C4 C6 1.509(6)
C4 C5 1.516(6)
C4 C7 1.523(6)
C8 C9 1.200(5)
C9 Si1 1.847(4)
C10 Si1 1.865(5)
C11 Si1 1.860(5)
C12 Si1 1.849(4)
C13 C14 1.517(5)
C13 C16 1.521(5)
C13 C15 1.528(5)
C13 S1 1.844(4)
N1 S1 1.671(3)
O1 S1 1.495(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5A O3 . 0.98 2.45 3.001(6) 115.5
C5 H5C O3 1_455 0.98 2.61 3.473(6) 147.5
C6 H6C O3 . 0.98 2.43 2.971(5) 114.5
C14 H14C O1 1_655 0.98 2.55 3.406(5) 145.6
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
C8 C1 C2 C3 61.4(4)
N1 C1 C2 C3 -176.6(3)
C1 C2 C3 O3 -127.9(4)
C1 C2 C3 O2 52.3(4)
C8 C1 N1 S1 -55.1(4)
C2 C1 N1 S1 -177.2(2)
O3 C3 O2 C4 0.1(6)
C2 C3 O2 C4 180.0(3)
C6 C4 O2 C3 -61.3(4)
C5 C4 O2 C3 63.2(4)
C7 C4 O2 C3 -179.4(4)
C1 N1 S1 O1 -84.7(3)
C1 N1 S1 C13 165.5(2)
C14 C13 S1 O1 -55.0(3)
C16 C13 S1 O1 -177.5(3)
C15 C13 S1 O1 64.2(3)
C14 C13 S1 N1 59.2(3)
C16 C13 S1 N1 -63.3(3)
C15 C13 S1 N1 178.4(3)
