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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/65/7106547.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_7106547
loop_
_publ_author_name
'Norman Lu'
'Wei-Hsuan Chang'
'Wen-Han Tu'
'Chieh-Keng Li'
_publ_section_title
;
 A salt made of 4-N,N-dimethylaminopyridine (DMAP) and saccharin as an
 efficient recyclable acylation catalyst: a new bridge between
 heterogeneous and homogeneous catalysis
;
_journal_name_full               Chem.Commun.
_journal_page_first              7227
_journal_paper_doi               10.1039/c1cc11556a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C14 H15 N3 O3 S1'
_chemical_formula_sum            'C14 H15 N3 O3 S'
_chemical_formula_weight         305.35
_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                90.00
_cell_angle_beta                 92.103(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1258(2)
_cell_length_b                   14.8941(5)
_cell_length_c                   13.4114(5)
_cell_measurement_reflns_used    7514
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     1422.43(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0849
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6053
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1.3676
_exptl_absorpt_correction_T_min  0.7582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0924
_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)+(0.1028P)²+6.7385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2651
_refine_ls_wR_factor_ref         0.2724
_reflns_number_gt                2131
_reflns_number_total             2423
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11556a.txt
_cod_data_source_block           10820
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7106547
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.3249(2) 0.38252(9) 0.27538(10) 0.0338(5) Uani 1 1 d . . .
O1 O 0.4970(8) 0.4080(3) 0.3274(3) 0.0546(13) Uani 1 1 d . . .
O2 O 0.1569(7) 0.3928(3) 0.3314(3) 0.0508(13) Uani 1 1 d . . .
O3 O 0.2811(7) 0.3899(3) 0.0034(3) 0.0434(11) Uani 1 1 d . . .
N1 N 0.3030(7) 0.4318(3) 0.1679(3) 0.0347(11) Uani 1 1 d . . .
N2 N 0.7795(7) 0.4360(4) 0.0366(4) 0.0412(12) Uani 1 1 d . . .
H2' H 0.7527 0.4996 0.0204 0.049 Uiso 1 1 d R . .
N3 N 0.8439(7) 0.1662(3) 0.0921(4) 0.0347(11) Uani 1 1 d . . .
C1 C 0.3013(8) 0.3708(4) 0.0944(4) 0.0313(12) Uani 1 1 d . . .
C2 C 0.3264(7) 0.2757(4) 0.1283(4) 0.0278(11) Uani 1 1 d . . .
C3 C 0.3433(7) 0.2713(4) 0.2308(4) 0.0275(11) Uani 1 1 d . . .
C4 C 0.3730(8) 0.1921(4) 0.2823(4) 0.0332(13) Uani 1 1 d . . .
H4 H 0.3835 0.1905 0.3531 0.040 Uiso 1 1 calc R . .
C5 C 0.3866(9) 0.1149(4) 0.2252(5) 0.0387(14) Uani 1 1 d . . .
H5 H 0.4098 0.0589 0.2574 0.046 Uiso 1 1 calc R . .
C6 C 0.3668(9) 0.1179(4) 0.1217(5) 0.0373(14) Uani 1 1 d . . .
H6 H 0.3752 0.0639 0.0845 0.045 Uiso 1 1 calc R . .
C7 C 0.3351(8) 0.1985(4) 0.0718(4) 0.0351(13) Uani 1 1 d . . .
H7 H 0.3199 0.2004 0.0012 0.042 Uiso 1 1 calc R . .
C8 C 0.8192(9) 0.4070(4) 0.1296(5) 0.0418(14) Uani 1 1 d . . .
H8 H 0.8323 0.4496 0.1821 0.050 Uiso 1 1 calc R . .
C9 C 0.8411(8) 0.3183(4) 0.1508(4) 0.0364(13) Uani 1 1 d . . .
H9 H 0.8685 0.2999 0.2176 0.044 Uiso 1 1 calc R . .
C10 C 0.8237(7) 0.2532(4) 0.0745(4) 0.0306(12) Uani 1 1 d . . .
C11 C 0.7829(10) 0.2872(4) -0.0227(4) 0.0414(15) Uani 1 1 d . . .
H11 H 0.7709 0.2468 -0.0774 0.050 Uiso 1 1 calc R . .
C12 C 0.7609(10) 0.3757(4) -0.0384(5) 0.0464(16) Uani 1 1 d . . .
H12 H 0.7315 0.3965 -0.1041 0.056 Uiso 1 1 calc R . .
C13 C 0.8804(10) 0.1340(5) 0.1949(5) 0.0468(16) Uani 1 1 d . . .
H13A H 0.8907 0.0684 0.1948 0.070 Uiso 1 1 calc R . .
H13B H 0.7768 0.1521 0.2366 0.070 Uiso 1 1 calc R . .
H13C H 0.9980 0.1601 0.2217 0.070 Uiso 1 1 calc R . .
C14 C 0.8262(11) 0.0996(4) 0.0127(5) 0.0468(16) Uani 1 1 d . . .
H14A H 0.8455 0.0395 0.0409 0.070 Uiso 1 1 calc R . .
H14B H 0.9208 0.1113 -0.0369 0.070 Uiso 1 1 calc R . .
H14C H 0.7005 0.1034 -0.0192 0.070 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
O1 S1 O2 115.3(3) . . ?
O1 S1 N1 111.4(3) . . ?
O2 S1 N1 111.1(3) . . ?
O1 S1 C3 109.8(3) . . ?
O2 S1 C3 110.4(3) . . ?
N1 S1 C3 97.4(2) . . ?
C1 N1 S1 110.2(4) . . ?
C8 N2 C12 119.3(5) . . ?
C8 N2 H2' 123.1 . . ?
C12 N2 H2' 117.4 . . ?
C10 N3 C14 121.9(5) . . ?
C10 N3 C13 120.0(5) . . ?
C14 N3 C13 118.1(5) . . ?
O3 C1 N1 123.9(5) . . ?
O3 C1 C2 121.2(5) . . ?
N1 C1 C2 114.8(5) . . ?
C3 C2 C7 120.3(5) . . ?
C3 C2 C1 110.7(5) . . ?
C7 C2 C1 129.0(5) . . ?
C2 C3 C4 123.1(5) . . ?
C2 C3 S1 106.7(4) . . ?
C4 C3 S1 130.1(4) . . ?
C3 C4 C5 116.5(5) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.2(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C2 C7 C6 117.7(5) . . ?
C2 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
N2 C8 C9 121.8(6) . . ?
N2 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 120.6(6) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N3 C10 C9 122.4(5) . . ?
N3 C10 C11 122.1(5) . . ?
C9 C10 C11 115.5(5) . . ?
C12 C11 C10 120.9(6) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 N2 121.9(6) . . ?
C11 C12 H12 119.1 . . ?
N2 C12 H12 119.1 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 O1 1.440(5) . ?
S1 O2 1.445(5) . ?
S1 N1 1.619(5) . ?
S1 C3 1.767(5) . ?
O3 C1 1.256(7) . ?
N1 C1 1.341(7) . ?
N2 C8 1.339(8) . ?
N2 C12 1.351(8) . ?
N2 H2' 0.9883 . ?
N3 C10 1.325(7) . ?
N3 C14 1.456(8) . ?
N3 C13 1.473(8) . ?
C1 C2 1.495(7) . ?
C2 C3 1.377(8) . ?
C2 C7 1.381(8) . ?
C3 C4 1.379(8) . ?
C4 C5 1.387(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.359(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.418(8) . ?
C11 C12 1.343(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653301
2 PubChem 139181952
