#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/77/7127771.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_7127771
loop_
_publ_author_name
'Wang, Jingjing'
'Liu, Xue'
'Wu, Ziyan'
'Li, Feng'
'Zhang, Ming-Liang'
'Mi, Yiman'
'Wei, Junhao'
'Zhou, Yao'
'Liu, Lantao'
_publ_section_title
;
 Ag-Catalyzed ring-opening of tertiary cycloalkanols for C-H
 functionalization of cyclic aldimines.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1506
_journal_page_last               1509
_journal_paper_doi               10.1039/d0cc07181a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C16 H13 N O4 S'
_chemical_formula_weight         315.33
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-12-19 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.833(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.556(2)
_cell_length_b                   5.6598(7)
_cell_length_c                   17.572(2)
_cell_measurement_reflns_used    3896
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.82
_cell_volume                     1482.0(3)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.1068
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20112
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0588
_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)+(0.0563P)²+0.4684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                1622
_reflns_number_total             2597
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc07181a2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7127770--7127771.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7127771
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.81756(6) 0.12515(19) 0.46152(5) 0.0594(3) Uani 1 1 d . . .
O1 O 0.74763(16) 0.0002(4) 0.37630(14) 0.0612(6) Uani 1 1 d . . .
O2 O 0.84754(19) -0.0616(5) 0.52012(15) 0.0886(9) Uani 1 1 d . . .
O3 O 0.87978(16) 0.2563(5) 0.44347(16) 0.0807(8) Uani 1 1 d . . .
O4 O 0.57726(18) 0.1989(5) 0.50430(15) 0.0880(10) Uani 1 1 d . . .
N1 N 0.75629(17) 0.3044(5) 0.48672(15) 0.0504(7) Uani 1 1 d . . .
C1 C 0.6166(2) 0.2025(7) 0.8005(2) 0.0567(9) Uani 1 1 d . . .
H1 H 0.6167 0.1715 0.8525 0.068 Uiso 1 1 calc R . .
C2 C 0.5753(2) 0.0473(6) 0.7343(2) 0.0551(9) Uani 1 1 d . . .
H13 H 0.5479 -0.0887 0.7415 0.066 Uiso 1 1 calc R . .
C3 C 0.5752(2) 0.0954(6) 0.6574(2) 0.0500(8) Uani 1 1 d . . .
H12 H 0.5469 -0.0086 0.6125 0.060 Uiso 1 1 calc R . .
C4 C 0.61616(18) 0.2954(6) 0.64584(17) 0.0417(8) Uani 1 1 d . . .
C5 C 0.61271(19) 0.3422(6) 0.56085(19) 0.0488(8) Uani 1 1 d . . .
C6 C 0.6526(2) 0.5629(6) 0.54530(19) 0.0535(9) Uani 1 1 d . . .
H9 H 0.7165 0.5649 0.5823 0.064 Uiso 1 1 calc R . .
H3 H 0.6258 0.6984 0.5593 0.064 Uiso 1 1 calc R . .
C7 C 0.6386(2) 0.5845(6) 0.4547(2) 0.0565(9) Uani 1 1 d . . .
H4 H 0.5749 0.5711 0.4179 0.068 Uiso 1 1 calc R . .
H5 H 0.6576 0.7408 0.4465 0.068 Uiso 1 1 calc R . .
C8 C 0.68744(19) 0.4054(5) 0.42809(18) 0.0415(7) Uani 1 1 d . . .
C9 C 0.65662(19) 0.3500(6) 0.33823(17) 0.0422(7) Uani 1 1 d . . .
C10 C 0.5933(2) 0.4878(6) 0.27362(19) 0.0541(9) Uani 1 1 d . . .
H8 H 0.5712 0.6245 0.2872 0.065 Uiso 1 1 calc R . .
C11 C 0.5635(2) 0.4232(7) 0.1906(2) 0.0640(10) Uani 1 1 d . . .
H7 H 0.5223 0.5179 0.1482 0.077 Uiso 1 1 calc R . .
C12 C 0.5942(2) 0.2194(8) 0.1699(2) 0.0661(11) Uani 1 1 d . . .
H2 H 0.5726 0.1751 0.1134 0.079 Uiso 1 1 calc R . .
C13 C 0.6868(2) 0.1492(6) 0.31431(19) 0.0476(8) Uani 1 1 d . . .
C14 C 0.6567(2) 0.0797(7) 0.2318(2) 0.0607(10) Uani 1 1 d . . .
H6 H 0.6779 -0.0580 0.2179 0.073 Uiso 1 1 calc R . .
C15 C 0.6578(2) 0.4495(6) 0.71329(18) 0.0474(8) Uani 1 1 d . . .
H11 H 0.6860 0.5849 0.7067 0.057 Uiso 1 1 calc R . .
C16 C 0.6573(2) 0.4009(6) 0.79033(19) 0.0539(9) Uani 1 1 d . . .
H10 H 0.6850 0.5045 0.8354 0.065 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 119.99(18) . . ?
O2 S1 O1 103.49(17) . . ?
O3 S1 O1 108.80(15) . . ?
O2 S1 N1 109.41(15) . . ?
O3 S1 N1 109.60(17) . . ?
O1 S1 N1 104.30(13) . . ?
C13 O1 S1 116.3(2) . . ?
C8 N1 S1 119.9(2) . . ?
C16 C1 C2 120.4(3) . . ?
C16 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H13 120.3 . . ?
C3 C2 H13 120.3 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H12 119.5 . . ?
C4 C3 H12 119.5 . . ?
C3 C4 C15 118.9(3) . . ?
C3 C4 C5 119.0(3) . . ?
C15 C4 C5 122.0(3) . . ?
O4 C5 C4 119.5(3) . . ?
O4 C5 C6 120.2(3) . . ?
C4 C5 C6 120.3(3) . . ?
C5 C6 C7 112.5(3) . . ?
C5 C6 H9 109.1 . . ?
C7 C6 H9 109.1 . . ?
C5 C6 H3 109.1 . . ?
C7 C6 H3 109.1 . . ?
H9 C6 H3 107.8 . . ?
C8 C7 C6 114.8(3) . . ?
C8 C7 H4 108.6 . . ?
C6 C7 H4 108.6 . . ?
C8 C7 H5 108.6 . . ?
C6 C7 H5 108.6 . . ?
H4 C7 H5 107.5 . . ?
N1 C8 C9 122.5(3) . . ?
N1 C8 C7 117.5(3) . . ?
C9 C8 C7 120.0(3) . . ?
C13 C9 C10 117.1(3) . . ?
C13 C9 C8 120.2(3) . . ?
C10 C9 C8 122.7(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H8 119.7 . . ?
C9 C10 H8 119.7 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H7 119.9 . . ?
C12 C11 H7 119.9 . . ?
C11 C12 C14 120.7(3) . . ?
C11 C12 H2 119.7 . . ?
C14 C12 H2 119.7 . . ?
C14 C13 C9 123.1(3) . . ?
C14 C13 O1 117.3(3) . . ?
C9 C13 O1 119.5(3) . . ?
C13 C14 C12 118.2(3) . . ?
C13 C14 H6 120.9 . . ?
C12 C14 H6 120.9 . . ?
C16 C15 C4 119.8(3) . . ?
C16 C15 H11 120.1 . . ?
C4 C15 H11 120.1 . . ?
C1 C16 C15 120.4(3) . . ?
C1 C16 H10 119.8 . . ?
C15 C16 H10 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.406(3) . ?
S1 O3 1.413(3) . ?
S1 O1 1.604(2) . ?
S1 N1 1.627(3) . ?
O1 C13 1.398(4) . ?
O4 C5 1.217(3) . ?
N1 C8 1.290(4) . ?
C1 C16 1.361(5) . ?
C1 C2 1.378(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(4) . ?
C2 H13 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H12 0.9300 . ?
C4 C15 1.389(4) . ?
C4 C5 1.493(4) . ?
C5 C6 1.493(5) . ?
C6 C7 1.511(4) . ?
C6 H9 0.9700 . ?
C6 H3 0.9700 . ?
C7 C8 1.493(4) . ?
C7 H4 0.9700 . ?
C7 H5 0.9700 . ?
C8 C9 1.466(4) . ?
C9 C13 1.379(4) . ?
C9 C10 1.400(4) . ?
C10 C11 1.370(4) . ?
C10 H8 0.9300 . ?
C11 C12 1.373(5) . ?
C11 H7 0.9300 . ?
C12 C14 1.378(5) . ?
C12 H2 0.9300 . ?
C13 C14 1.370(4) . ?
C14 H6 0.9300 . ?
C15 C16 1.385(4) . ?
C15 H11 0.9300 . ?
C16 H10 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 O1 C13 161.1(2) . . . . ?
O3 S1 O1 C13 -70.2(2) . . . . ?
N1 S1 O1 C13 46.7(2) . . . . ?
O2 S1 N1 C8 -143.7(3) . . . . ?
O3 S1 N1 C8 82.8(3) . . . . ?
O1 S1 N1 C8 -33.5(3) . . . . ?
C16 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C15 -0.2(5) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C3 C4 C5 O4 -3.1(5) . . . . ?
C15 C4 C5 O4 178.3(3) . . . . ?
C3 C4 C5 C6 177.1(3) . . . . ?
C15 C4 C5 C6 -1.6(4) . . . . ?
O4 C5 C6 C7 2.9(5) . . . . ?
C4 C5 C6 C7 -177.2(3) . . . . ?
C5 C6 C7 C8 -66.9(4) . . . . ?
S1 N1 C8 C9 5.5(4) . . . . ?
S1 N1 C8 C7 -174.6(2) . . . . ?
C6 C7 C8 N1 -21.8(4) . . . . ?
C6 C7 C8 C9 158.1(3) . . . . ?
N1 C8 C9 C13 15.4(4) . . . . ?
C7 C8 C9 C13 -164.5(3) . . . . ?
N1 C8 C9 C10 -167.7(3) . . . . ?
C7 C8 C9 C10 12.4(4) . . . . ?
C13 C9 C10 C11 -0.1(4) . . . . ?
C8 C9 C10 C11 -177.1(3) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C14 -1.4(5) . . . . ?
C10 C9 C13 C14 -1.1(5) . . . . ?
C8 C9 C13 C14 176.0(3) . . . . ?
C10 C9 C13 O1 -177.6(3) . . . . ?
C8 C9 C13 O1 -0.6(4) . . . . ?
S1 O1 C13 C14 150.5(2) . . . . ?
S1 O1 C13 C9 -32.7(4) . . . . ?
C9 C13 C14 C12 0.9(5) . . . . ?
O1 C13 C14 C12 177.6(3) . . . . ?
C11 C12 C14 C13 0.3(5) . . . . ?
C3 C4 C15 C16 -0.2(4) . . . . ?
C5 C4 C15 C16 178.4(3) . . . . ?
C2 C1 C16 C15 0.0(5) . . . . ?
C4 C15 C16 C1 0.3(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352484
