#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/58/1545890.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_1545890
loop_
_publ_author_name
'Saputra, Mirza A.'
'Dange, Nitin S.'
'Cleveland, Alexander H.'
'Malone, Joshua A.'
'Fronczek, Frank R.'
'Kartika, Rendy'
_publ_section_title
;
 Regioselective Functionalization of Enamides at the α-Carbon via
 Unsymmetrical 2-Amidoallyl Cations.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2414
_journal_page_last               2417
_journal_paper_doi               10.1021/acs.orglett.7b00962
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C19 H21 N O3 S'
_chemical_formula_sum            'C19 H21 N O3 S'
_chemical_formula_weight         343.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
_cell_angle_beta                 100.835(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0294(2)
_cell_length_b                   32.1226(12)
_cell_length_c                   8.9796(4)
_cell_measurement_reflns_used    8736
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      31.86
_cell_measurement_theta_min      3.43
_cell_volume                     1708.16(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24680
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.8927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         5928
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.9143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                4933
_reflns_number_total             5928
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol7b00962_si_001.cif
_cod_data_source_block           NSD-2073
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1545888--1545892.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               1545890
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.42559(5) 0.823635(11) 0.33061(4) 0.02081(9) Uani 1 1 d .
O1 O 0.60177(17) 0.84889(4) 0.28912(14) 0.0307(3) Uani 1 1 d .
O2 O 0.4796(2) 0.78459(4) 0.40540(14) 0.0378(3) Uani 1 1 d .
O3 O 0.63567(16) 0.92548(3) 0.44506(12) 0.0210(2) Uani 1 1 d D
H3O H 0.646(3) 0.9035(5) 0.400(2) 0.031 Uiso 1 1 d D
N1 N 0.30808(18) 0.85248(3) 0.44627(12) 0.0152(2) Uani 1 1 d .
C1 C 0.25644(19) 0.89467(4) 0.39781(13) 0.0119(2) Uani 1 1 d .
C2 C 0.40837(19) 0.93009(4) 0.46787(13) 0.0130(2) Uani 1 1 d .
C3 C 0.2966(2) 0.96847(4) 0.37783(14) 0.0173(2) Uani 1 1 d .
H3A H 0.2709 0.9908 0.4485 0.021 Uiso 1 1 calc R
H3B H 0.3957 0.9794 0.3107 0.021 Uiso 1 1 calc R
C4 C 0.0687(2) 0.95375(4) 0.28256(15) 0.0181(2) Uani 1 1 d .
H4A H -0.0601 0.9658 0.3220 0.022 Uiso 1 1 calc R
H4B H 0.0559 0.9618 0.1749 0.022 Uiso 1 1 calc R
C5 C 0.0750(2) 0.90730(4) 0.29972(13) 0.0137(2) Uani 1 1 d .
H5 H -0.0370 0.8891 0.2470 0.016 Uiso 1 1 calc R
C6 C 0.4111(2) 0.93312(4) 0.63816(13) 0.0126(2) Uani 1 1 d .
C7 C 0.6058(2) 0.92434(4) 0.74405(15) 0.0189(2) Uani 1 1 d .
H7 H 0.7383 0.9153 0.7106 0.023 Uiso 1 1 calc R
C8 C 0.6076(2) 0.92870(5) 0.89873(16) 0.0239(3) Uani 1 1 d .
H8 H 0.7412 0.9225 0.9699 0.029 Uiso 1 1 calc R
C9 C 0.4165(3) 0.94190(5) 0.94956(15) 0.0229(3) Uani 1 1 d .
H9 H 0.4194 0.9456 1.0549 0.027 Uiso 1 1 calc R
C10 C 0.2200(2) 0.94974(4) 0.84469(15) 0.0203(3) Uani 1 1 d .
H10 H 0.0871 0.9583 0.8787 0.024 Uiso 1 1 calc R
C11 C 0.2172(2) 0.94516(4) 0.69027(14) 0.0166(2) Uani 1 1 d .
H11 H 0.0817 0.9503 0.6196 0.020 Uiso 1 1 calc R
C12 C 0.1391(3) 0.83182(4) 0.52046(16) 0.0236(3) Uani 1 1 d .
H12A H 0.1093 0.8492 0.6043 0.035 Uiso 1 1 calc R
H12B H 0.1970 0.8047 0.5598 0.035 Uiso 1 1 calc R
H12C H -0.0012 0.8279 0.4466 0.035 Uiso 1 1 calc R
C13 C 0.2201(2) 0.81540(4) 0.16720(14) 0.0161(2) Uani 1 1 d .
C14 C 0.0558(2) 0.78493(4) 0.16705(15) 0.0206(3) Uani 1 1 d .
H14 H 0.0648 0.7662 0.2499 0.025 Uiso 1 1 calc R
C15 C -0.1215(2) 0.78229(4) 0.04388(15) 0.0217(3) Uani 1 1 d .
H15 H -0.2339 0.7615 0.0427 0.026 Uiso 1 1 calc R
C16 C -0.1371(2) 0.80971(4) -0.07825(14) 0.0194(3) Uani 1 1 d .
C17 C 0.0317(3) 0.83941(5) -0.07595(15) 0.0221(3) Uani 1 1 d .
H17 H 0.0242 0.8579 -0.1593 0.026 Uiso 1 1 calc R
C18 C 0.2104(2) 0.84251(4) 0.04561(15) 0.0198(3) Uani 1 1 d .
H18 H 0.3247 0.8629 0.0458 0.024 Uiso 1 1 calc R
C19 C -0.3351(3) 0.80787(5) -0.20861(17) 0.0308(3) Uani 1 1 d .
H19A H -0.4495 0.8281 -0.1921 0.046 Uiso 1 1 calc R
H19B H -0.4004 0.7798 -0.2152 0.046 Uiso 1 1 calc R
H19C H -0.2841 0.8144 -0.3033 0.046 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
O2 S1 O1 120.09(8)
O2 S1 N1 106.49(7)
O1 S1 N1 105.77(6)
O2 S1 C13 108.85(6)
O1 S1 C13 107.94(7)
N1 S1 C13 106.99(6)
C2 O3 H3O 108.7(15)
C1 N1 C12 115.56(11)
C1 N1 S1 115.66(8)
C12 N1 S1 116.54(9)
C5 C1 N1 126.19(11)
C5 C1 C2 113.68(11)
N1 C1 C2 120.01(10)
O3 C2 C1 112.46(10)
O3 C2 C6 108.61(10)
C1 C2 C6 110.71(10)
O3 C2 C3 109.90(10)
C1 C2 C3 102.09(9)
C6 C2 C3 113.03(10)
C4 C3 C2 107.31(10)
C4 C3 H3A 110.3
C2 C3 H3A 110.3
C4 C3 H3B 110.3
C2 C3 H3B 110.3
H3A C3 H3B 108.5
C5 C4 C3 104.13(10)
C5 C4 H4A 110.9
C3 C4 H4A 110.9
C5 C4 H4B 110.9
C3 C4 H4B 110.9
H4A C4 H4B 108.9
C1 C5 C4 111.87(11)
C1 C5 H5 124.1
C4 C5 H5 124.1
C11 C6 C7 118.64(11)
C11 C6 C2 120.10(11)
C7 C6 C2 121.25(11)
C6 C7 C8 120.49(13)
C6 C7 H7 119.8
C8 C7 H7 119.8
C9 C8 C7 120.57(13)
C9 C8 H8 119.7
C7 C8 H8 119.7
C8 C9 C10 119.24(12)
C8 C9 H9 120.4
C10 C9 H9 120.4
C9 C10 C11 120.33(13)
C9 C10 H10 119.8
C11 C10 H10 119.8
C10 C11 C6 120.68(12)
C10 C11 H11 119.7
C6 C11 H11 119.7
N1 C12 H12A 109.5
N1 C12 H12B 109.5
H12A C12 H12B 109.5
N1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C18 C13 C14 121.01(12)
C18 C13 S1 118.80(10)
C14 C13 S1 119.84(10)
C15 C14 C13 118.99(12)
C15 C14 H14 120.5
C13 C14 H14 120.5
C14 C15 C16 121.01(13)
C14 C15 H15 119.5
C16 C15 H15 119.5
C17 C16 C15 118.67(12)
C17 C16 C19 120.55(13)
C15 C16 C19 120.77(13)
C18 C17 C16 121.25(13)
C18 C17 H17 119.4
C16 C17 H17 119.4
C17 C18 C13 119.05(12)
C17 C18 H18 120.5
C13 C18 H18 120.5
C16 C19 H19A 109.5
C16 C19 H19B 109.5
H19A C19 H19B 109.5
C16 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4311(12)
S1 O1 1.4402(12)
S1 N1 1.6479(11)
S1 C13 1.7536(12)
O3 C2 1.4310(15)
O3 H3O 0.820(15)
N1 C1 1.4396(16)
N1 C12 1.4754(18)
C1 C5 1.3325(16)
C1 C2 1.5209(16)
C2 C6 1.5292(17)
C2 C3 1.5566(18)
C3 C4 1.5497(18)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.5000(18)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5 0.9500
C6 C11 1.3931(17)
C6 C7 1.3935(17)
C7 C8 1.3940(19)
C7 H7 0.9500
C8 C9 1.383(2)
C8 H8 0.9500
C9 C10 1.391(2)
C9 H9 0.9500
C10 C11 1.3914(18)
C10 H10 0.9500
C11 H11 0.9500
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C18 1.3892(19)
C13 C14 1.3925(19)
C14 C15 1.3886(18)
C14 H14 0.9500
C15 C16 1.3960(19)
C15 H15 0.9500
C16 C17 1.392(2)
C16 C19 1.5080(19)
C17 C18 1.3858(19)
C17 H17 0.9500
C18 H18 0.9500
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3O O1 0.820(15) 2.012(15) 2.8193(15) 168(2)
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
O2 S1 N1 C1 175.23(9)
O1 S1 N1 C1 46.41(10)
C13 S1 N1 C1 -68.49(10)
O2 S1 N1 C12 -43.96(11)
O1 S1 N1 C12 -172.78(10)
C13 S1 N1 C12 72.32(11)
C12 N1 C1 C5 -59.43(16)
S1 N1 C1 C5 81.77(14)
C12 N1 C1 C2 116.38(12)
S1 N1 C1 C2 -102.42(11)
C5 C1 C2 O3 -123.99(12)
N1 C1 C2 O3 59.71(14)
C5 C1 C2 C6 114.32(12)
N1 C1 C2 C6 -61.99(14)
C5 C1 C2 C3 -6.26(13)
N1 C1 C2 C3 177.43(10)
O3 C2 C3 C4 128.75(11)
C1 C2 C3 C4 9.21(12)
C6 C2 C3 C4 -109.73(11)
C2 C3 C4 C5 -9.14(13)
N1 C1 C5 C4 176.58(11)
C2 C1 C5 C4 0.54(15)
C3 C4 C5 C1 5.51(14)
O3 C2 C6 C11 168.51(11)
C1 C2 C6 C11 -67.56(14)
C3 C2 C6 C11 46.26(15)
O3 C2 C6 C7 -10.96(16)
C1 C2 C6 C7 112.97(13)
C3 C2 C6 C7 -133.20(12)
C11 C6 C7 C8 -1.8(2)
C2 C6 C7 C8 177.70(12)
C6 C7 C8 C9 -0.2(2)
C7 C8 C9 C10 1.7(2)
C8 C9 C10 C11 -1.3(2)
C9 C10 C11 C6 -0.7(2)
C7 C6 C11 C10 2.22(19)
C2 C6 C11 C10 -177.26(12)
O2 S1 C13 C18 -152.38(11)
O1 S1 C13 C18 -20.52(12)
N1 S1 C13 C18 92.91(11)
O2 S1 C13 C14 34.40(14)
O1 S1 C13 C14 166.27(11)
N1 S1 C13 C14 -80.30(12)
C18 C13 C14 C15 -1.0(2)
S1 C13 C14 C15 172.11(11)
C13 C14 C15 C16 -0.3(2)
C14 C15 C16 C17 1.3(2)
C14 C15 C16 C19 -177.39(14)
C15 C16 C17 C18 -1.1(2)
C19 C16 C17 C18 177.59(14)
C16 C17 C18 C13 -0.1(2)
C14 C13 C18 C17 1.2(2)
S1 C13 C18 C17 -171.98(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139049975
