#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:24:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178468 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028998.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_4028998
loop_
_publ_author_name
'Bosque, Irene'
'Bagdatli, Emine'
'Foubelo, Francisco'
'Gonzalez-Gomez, Jose C'
_publ_section_title
;
 Regio- and stereoselective aminopentadienylation of carbonyl compounds.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1796
_journal_page_last               1804
_journal_paper_doi               10.1021/jo402854z
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H29 N O S'
_chemical_formula_sum            'C16 H29 N O S'
_chemical_formula_weight         283.46
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.081(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2041(14)
_cell_length_b                   9.0692(12)
_cell_length_c                   10.6334(15)
_cell_measurement_reflns_used    1658
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      19.93
_cell_measurement_theta_min      2.17
_cell_volume                     868.2(2)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9167
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.8399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0427P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                3239
_reflns_number_total             3978
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo402854z_si_002.cif
_cod_data_source_block           xnm
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028998
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
S1 S -0.07403(5) 0.78582(6) 0.85130(6) 0.03070(14) Uani 1 1 d .
O1 O -0.07228(16) 0.84865(18) 0.98193(17) 0.0400(4) Uani 1 1 d .
N1 N 0.04961(19) 0.6545(2) 0.88778(19) 0.0281(4) Uani 1 1 d .
H1N H 0.045(2) 0.567(3) 0.934(2) 0.024(6) Uiso 1 1 d .
C1 C 0.2017(2) 0.6961(2) 0.9203(2) 0.0262(5) Uani 1 1 d .
H1 H 0.2092 0.8036 0.9312 0.031 Uiso 1 1 calc R
C2 C 0.3152(2) 0.6286(3) 1.0641(2) 0.0276(5) Uani 1 1 d .
H2 H 0.3045 0.5211 1.0553 0.033 Uiso 1 1 calc R
C3 C 0.4708(2) 0.6652(3) 1.0975(2) 0.0365(6) Uani 1 1 d .
H3 H 0.4929 0.7641 1.0941 0.044 Uiso 1 1 calc R
C4 C 0.5794(3) 0.5698(4) 1.1314(3) 0.0551(8) Uani 1 1 d .
H4A H 0.5622 0.4697 1.1361 0.066 Uiso 1 1 calc R
H4B H 0.6734 0.6024 1.1507 0.066 Uiso 1 1 calc R
C5 C 0.2844(3) 0.6754(3) 1.1841(2) 0.0360(5) Uani 1 1 d .
H5 H 0.1853 0.6861 1.1624 0.043 Uiso 1 1 calc R
C6 C 0.3838(3) 0.7021(3) 1.3152(3) 0.0468(7) Uani 1 1 d .
H6A H 0.4843 0.6927 1.3418 0.056 Uiso 1 1 calc R
H6B H 0.3543 0.7304 1.3821 0.056 Uiso 1 1 calc R
C7 C 0.2315(2) 0.6567(3) 0.7953(2) 0.0292(5) Uani 1 1 d .
H7 H 0.3354 0.6819 0.8249 0.035 Uiso 1 1 calc R
C8 C 0.1362(2) 0.7501(3) 0.6647(2) 0.0340(6) Uani 1 1 d .
H8A H 0.1567 0.8536 0.6893 0.041 Uiso 1 1 calc R
H8B H 0.0322 0.7327 0.6364 0.041 Uiso 1 1 calc R
C9 C 0.1651(3) 0.7156(3) 0.5394(3) 0.0431(6) Uani 1 1 d .
H9A H 0.0974 0.7722 0.4568 0.052 Uiso 1 1 calc R
H9B H 0.2657 0.7440 0.5631 0.052 Uiso 1 1 calc R
C10 C 0.1440(3) 0.5535(3) 0.5039(3) 0.0521(7) Uani 1 1 d .
H10A H 0.1687 0.5332 0.4280 0.063 Uiso 1 1 calc R
H10B H 0.0405 0.5277 0.4700 0.063 Uiso 1 1 calc R
C11 C 0.2406(3) 0.4590(3) 0.6327(3) 0.0489(7) Uani 1 1 d .
H11A H 0.3443 0.4767 0.6600 0.059 Uiso 1 1 calc R
H11B H 0.2198 0.3558 0.6075 0.059 Uiso 1 1 calc R
C12 C 0.2132(3) 0.4927(3) 0.7590(3) 0.0375(6) Uani 1 1 d .
H12A H 0.2826 0.4368 0.8412 0.045 Uiso 1 1 calc R
H12B H 0.1135 0.4621 0.7364 0.045 Uiso 1 1 calc R
C13 C -0.2429(2) 0.6704(3) 0.7696(2) 0.0325(5) Uani 1 1 d .
C14 C -0.2448(3) 0.5815(3) 0.6476(3) 0.0465(7) Uani 1 1 d .
H14A H -0.1694 0.5068 0.6851 0.070 Uiso 1 1 calc R
H14B H -0.2258 0.6458 0.5862 0.070 Uiso 1 1 calc R
H14C H -0.3403 0.5360 0.5942 0.070 Uiso 1 1 calc R
C15 C -0.3716(2) 0.7815(4) 0.7096(3) 0.0536(7) Uani 1 1 d .
H15A H -0.4644 0.7294 0.6661 0.080 Uiso 1 1 calc R
H15B H -0.3638 0.8425 0.6396 0.080 Uiso 1 1 calc R
H15C H -0.3671 0.8421 0.7856 0.080 Uiso 1 1 calc R
C16 C -0.2494(3) 0.5745(3) 0.8820(3) 0.0487(7) Uani 1 1 d .
H16A H -0.2422 0.6350 0.9591 0.073 Uiso 1 1 calc R
H16B H -0.1685 0.5056 0.9171 0.073 Uiso 1 1 calc R
H16C H -0.3418 0.5216 0.8415 0.073 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
O1 S1 N1 112.66(9)
O1 S1 C13 104.69(10)
N1 S1 C13 98.22(10)
C1 N1 S1 118.51(15)
N1 C1 C7 110.66(17)
N1 C1 C2 110.31(17)
C7 C1 C2 113.69(17)
C3 C2 C5 110.93(19)
C3 C2 C1 111.43(18)
C5 C2 C1 111.54(18)
C4 C3 C2 125.7(3)
C6 C5 C2 126.0(2)
C8 C7 C12 111.19(18)
C8 C7 C1 110.94(18)
C12 C7 C1 113.29(19)
C7 C8 C9 112.27(19)
C10 C9 C8 110.8(2)
C9 C10 C11 111.6(2)
C10 C11 C12 111.7(2)
C11 C12 C7 111.6(2)
C16 C13 C14 112.6(2)
C16 C13 C15 111.1(2)
C14 C13 C15 109.2(2)
C16 C13 S1 109.54(16)
C14 C13 S1 109.61(16)
C15 C13 S1 104.44(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4937(16)
S1 N1 1.6431(19)
S1 C13 1.847(2)
N1 C1 1.472(3)
C1 C7 1.538(3)
C1 C2 1.545(3)
C2 C3 1.492(3)
C2 C5 1.511(3)
C3 C4 1.316(4)
C5 C6 1.304(3)
C7 C8 1.523(3)
C7 C12 1.526(3)
C8 C9 1.527(3)
C9 C10 1.508(4)
C10 C11 1.520(4)
C11 C12 1.525(3)
C13 C16 1.504(3)
C13 C14 1.520(3)
C13 C15 1.536(3)
