#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/55/1515527.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_1515527
loop_
_publ_author_name
'Lu, Hongjian'
'Jiang, Huiling'
'Hu, Yang'
'Wojtas, Lukasz'
'Zhang, X. Peter'
_publ_section_title
;
 Chemoselective intramolecular allylic C--H amination versus CC
 aziridination through Co(ii)-based metalloradical catalysis
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              2361
_journal_paper_doi               10.1039/c1sc00366f
_journal_volume                  2
_journal_year                    2011
_chemical_formula_moiety         'C16 H22 N2 O2 S'
_chemical_formula_sum            'C16 H22 N2 O2 S'
_chemical_formula_weight         306.42
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.3076(3)
_cell_length_b                   9.7760(3)
_cell_length_c                   26.6952(7)
_cell_measurement_reflns_used    4696
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.25
_cell_measurement_theta_min      3.31
_cell_volume                     3211.94(15)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega 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  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32841
_diffrn_reflns_theta_full        67.12
_diffrn_reflns_theta_max         67.12
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  0.9301
_exptl_absorpt_correction_T_min  0.8096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0557P)²+1.6968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2398
_reflns_number_total             2859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00366f.txt
_cod_data_source_block           hjl_8_118
_cod_original_sg_symbol_Hall     -P2ac2ab
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1515527
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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 0.28053(3) 0.05056(4) 0.410352(16) 0.02063(16) Uani 1 1 d .
O1 O 0.16832(11) 0.05422(14) 0.39685(5) 0.0276(3) Uani 1 1 d .
O2 O 0.31945(11) -0.07391(13) 0.43283(5) 0.0269(3) Uani 1 1 d .
N1 N 0.35155(13) 0.08796(16) 0.35991(6) 0.0247(4) Uani 1 1 d .
N2 N 0.30579(13) 0.17375(16) 0.44842(6) 0.0212(3) Uani 1 1 d .
H2 H 0.2672(19) 0.245(3) 0.4413(9) 0.032 Uiso 1 1 d .
C1 C 0.4269(2) 0.1577(3) 0.17749(9) 0.0551(8) Uani 1 1 d .
H1 H 0.4475 0.1942 0.1467 0.066 Uiso 1 1 calc R
C2 C 0.4754(2) 0.0406(3) 0.19486(9) 0.0508(7) Uani 1 1 d .
H2A H 0.5286 -0.0024 0.1758 0.061 Uiso 1 1 calc R
C3 C 0.44542(19) -0.0136(3) 0.24043(8) 0.0398(5) Uani 1 1 d .
H3 H 0.4790 -0.0928 0.2519 0.048 Uiso 1 1 calc R
C4 C 0.36601(17) 0.0481(2) 0.26931(7) 0.0287(5) Uani 1 1 d .
C5 C 0.33231(18) -0.0113(2) 0.31871(7) 0.0300(5) Uani 1 1 d .
H5A H 0.2558 -0.0350 0.3176 0.036 Uiso 1 1 calc R
H5B H 0.3733 -0.0942 0.3251 0.036 Uiso 1 1 calc R
C6 C 0.46700(15) 0.1262(2) 0.36863(7) 0.0257(4) Uani 1 1 d .
H6 H 0.4938 0.1627 0.3367 0.031 Uiso 1 1 calc R
C7 C 0.47586(15) 0.2435(2) 0.40654(7) 0.0241(4) Uani 1 1 d .
H7 H 0.4360 0.3216 0.3926 0.029 Uiso 1 1 calc R
C8 C 0.42186(15) 0.20661(19) 0.45703(7) 0.0234(4) Uani 1 1 d .
H8 H 0.4583 0.1264 0.4713 0.028 Uiso 1 1 calc R
C9 C 0.42637(16) 0.3220(2) 0.49412(7) 0.0270(4) Uani 1 1 d .
H9 H 0.3845 0.3992 0.4877 0.032 Uiso 1 1 calc R
C10 C 0.48522(18) 0.3209(2) 0.53476(8) 0.0325(5) Uani 1 1 d .
H10A H 0.5280 0.2453 0.5423 0.039 Uiso 1 1 calc R
H10B H 0.4844 0.3959 0.5562 0.039 Uiso 1 1 calc R
C11 C 0.3477(2) 0.2213(3) 0.20560(9) 0.0501(7) Uani 1 1 d .
H11 H 0.3149 0.3008 0.1939 0.060 Uiso 1 1 calc R
C12 C 0.31702(19) 0.1668(2) 0.25141(8) 0.0364(5) Uani 1 1 d .
H12 H 0.2634 0.2097 0.2703 0.044 Uiso 1 1 calc R
C13 C 0.59488(17) 0.2867(2) 0.41155(8) 0.0311(5) Uani 1 1 d .
H13A H 0.6184 0.3277 0.3803 0.037 Uiso 1 1 calc R
H13B H 0.6007 0.3557 0.4375 0.037 Uiso 1 1 calc R
C14 C 0.67054(18) 0.1677(2) 0.42436(9) 0.0391(5) Uani 1 1 d .
H14A H 0.7451 0.1999 0.4250 0.047 Uiso 1 1 calc R
H14B H 0.6529 0.1329 0.4574 0.047 Uiso 1 1 calc R
C15 C 0.65961(18) 0.0534(2) 0.38605(10) 0.0424(6) Uani 1 1 d .
H15A H 0.7049 -0.0232 0.3959 0.051 Uiso 1 1 calc R
H15B H 0.6846 0.0855 0.3537 0.051 Uiso 1 1 calc R
C16 C 0.54175(18) 0.0062(2) 0.38182(9) 0.0342(5) Uani 1 1 d .
H16A H 0.5189 -0.0337 0.4134 0.041 Uiso 1 1 calc R
H16B H 0.5361 -0.0636 0.3561 0.041 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'
S S 0.3331 0.5567 '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 O2 116.65(8)
O1 S1 N2 109.16(8)
O2 S1 N2 107.81(8)
O1 S1 N1 107.54(8)
O2 S1 N1 110.62(8)
N2 S1 N1 104.37(8)
C5 N1 C6 115.61(15)
C5 N1 S1 112.08(12)
C6 N1 S1 115.78(13)
C8 N2 S1 116.57(12)
C8 N2 H2 112.7(16)
S1 N2 H2 111.2(16)
C2 C1 C11 120.0(2)
C2 C1 H1 120.0
C11 C1 H1 120.0
C1 C2 C3 120.2(2)
C1 C2 H2A 119.9
C3 C2 H2A 119.9
C2 C3 C4 120.9(2)
C2 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C12 118.6(2)
C3 C4 C5 121.1(2)
C12 C4 C5 120.31(19)
N1 C5 C4 110.75(16)
N1 C5 H5A 109.5
C4 C5 H5A 109.5
N1 C5 H5B 109.5
C4 C5 H5B 109.5
H5A C5 H5B 108.1
N1 C6 C16 114.65(16)
N1 C6 C7 111.05(15)
C16 C6 C7 112.23(17)
N1 C6 H6 106.1
C16 C6 H6 106.1
C7 C6 H6 106.1
C13 C7 C6 109.39(16)
C13 C7 C8 113.56(16)
C6 C7 C8 111.74(15)
C13 C7 H7 107.3
C6 C7 H7 107.3
C8 C7 H7 107.3
N2 C8 C9 107.49(15)
N2 C8 C7 109.26(15)
C9 C8 C7 112.56(15)
N2 C8 H8 109.2
C9 C8 H8 109.2
C7 C8 H8 109.2
C10 C9 C8 124.25(19)
C10 C9 H9 117.9
C8 C9 H9 117.9
C9 C10 H10A 120.0
C9 C10 H10B 120.0
H10A C10 H10B 120.0
C1 C11 C12 120.0(2)
C1 C11 H11 120.0
C12 C11 H11 120.0
C11 C12 C4 120.3(2)
C11 C12 H12 119.8
C4 C12 H12 119.8
C14 C13 C7 113.14(17)
C14 C13 H13A 109.0
C7 C13 H13A 109.0
C14 C13 H13B 109.0
C7 C13 H13B 109.0
H13A C13 H13B 107.8
C15 C14 C13 110.78(19)
C15 C14 H14A 109.5
C13 C14 H14A 109.5
C15 C14 H14B 109.5
C13 C14 H14B 109.5
H14A C14 H14B 108.1
C14 C15 C16 110.85(18)
C14 C15 H15A 109.5
C16 C15 H15A 109.5
C14 C15 H15B 109.5
C16 C15 H15B 109.5
H15A C15 H15B 108.1
C15 C16 C6 110.88(17)
C15 C16 H16A 109.5
C6 C16 H16A 109.5
C15 C16 H16B 109.5
C6 C16 H16B 109.5
H16A C16 H16B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4277(14)
S1 O2 1.4388(14)
S1 N2 1.6062(16)
S1 N1 1.6466(16)
N1 C5 1.485(2)
N1 C6 1.488(2)
N2 C8 1.482(2)
N2 H2 0.87(3)
C1 C2 1.372(4)
C1 C11 1.378(4)
C1 H1 0.9300
C2 C3 1.377(4)
C2 H2A 0.9300
C3 C4 1.383(3)
C3 H3 0.9300
C4 C12 1.392(3)
C4 C5 1.499(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C16 1.532(3)
C6 C7 1.533(3)
C6 H6 0.9800
C7 C13 1.530(3)
C7 C8 1.546(3)
C7 H7 0.9800
C8 C9 1.502(3)
C8 H8 0.9800
C9 C10 1.305(3)
C9 H9 0.9300
C10 H10A 0.9300
C10 H10B 0.9300
C11 C12 1.387(3)
C11 H11 0.9300
C12 H12 0.9300
C13 C14 1.528(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.521(3)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.526(3)
C15 H15A 0.9700
C15 H15B 0.9700
C16 H16A 0.9700
C16 H16B 0.9700
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043045
