#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507544.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_1507544
loop_
_publ_author_name
'Hof, Fraser'
'Iovine, Peter M.'
'Johnson, Darren W.'
'Rebek, Julius'
_publ_contact_author
;
Julius Rebek, Jr.
Skaggs Institute for Chemical Biology (MB26)
The Scripps Research Institute
10550 N. Torrey Pines Road
La Jolla, CA  92037
;
_publ_section_title
;
 Highly Selective Synthesis of Heterosubstituted Aromatic Sulfamides
;
_journal_issue                   26
_journal_name_full               'Organic Letters'
_journal_page_first              4247
_journal_paper_doi               10.1021/ol0169731
_journal_volume                  3
_journal_year                    2001
_chemical_compound_source        synthetic
_chemical_formula_sum            'C25 H45 N3 O4 S'
_chemical_formula_weight         483.70
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 97.160(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3003(5)
_cell_length_b                   13.8825(8)
_cell_length_c                   11.6167(7)
_cell_measurement_reflns_used    5271
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      51.60
_cell_measurement_theta_min      3.84
_cell_volume                     1328.14(14)
_computing_cell_refinement
;
SMART (Siemens, 1995), SAINT (Siemens, 1995)
;
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction
;
SAINT (Siemens, 1995), XPREP (Siemens, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      118(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  '3 circle diffractometer'
_diffrn_measurement_method
;
omega scans with profile analysis
;
_diffrn_radiation_detector       'CCD area detector'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5255
_diffrn_reflns_theta_full        51.70
_diffrn_reflns_theta_max         51.70
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.373
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0508
_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)+(0.1182P)²+0.1510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                2309
_reflns_number_total             2376
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0169731_s2.cif
_cod_data_source_block           hofsalts
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1507544
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 0.63430(12) 0.40563(7) -0.11063(8) 0.0225(4) Uani 1 1 d .
O1 O 0.5046(3) 0.3490(2) -0.0751(3) 0.0292(8) Uani 1 1 d .
O2 O 0.7917(3) 0.3849(2) -0.0476(2) 0.0272(8) Uani 1 1 d .
O3 O 0.6737(4) 0.2236(2) -0.2359(3) 0.0280(8) Uani 1 1 d .
O4 O 0.6980(4) 0.2934(2) -0.4086(2) 0.0291(8) Uani 1 1 d .
N1 N 0.5955(4) 0.5150(3) -0.1218(3) 0.0237(9) Uani 1 1 d .
N2 N 0.6510(4) 0.3858(3) -0.2563(3) 0.0236(9) Uani 1 1 d .
N3 N 0.8816(4) 0.0898(3) 0.0757(3) 0.0204(9) Uani 1 1 d .
C1 C 0.6205(5) 0.5480(3) -0.2311(4) 0.0227(11) Uani 1 1 d .
C2 C 0.6531(5) 0.4780(3) -0.3106(4) 0.0213(11) Uani 1 1 d .
C3 C 0.6807(6) 0.5018(4) -0.4226(4) 0.0314(13) Uani 1 1 d .
H3A H 0.6987 0.4531 -0.4770 0.038 Uiso 1 1 calc R
C4 C 0.6814(6) 0.5986(4) -0.4532(4) 0.0336(13) Uani 1 1 d .
H4A H 0.7031 0.6167 -0.5286 0.040 Uiso 1 1 calc R
C5 C 0.6509(6) 0.6682(4) -0.3748(4) 0.0336(12) Uani 1 1 d .
H5A H 0.6503 0.7340 -0.3975 0.040 Uiso 1 1 calc R
C6 C 0.6209(5) 0.6451(3) -0.2637(4) 0.0265(12) Uani 1 1 d .
H6A H 0.6009 0.6942 -0.2104 0.032 Uiso 1 1 calc R
C7 C 0.6758(5) 0.2934(4) -0.2966(4) 0.0235(11) Uani 1 1 d .
C8 C 0.7247(6) 0.1992(3) -0.4571(4) 0.0316(13) Uani 1 1 d .
H8A H 0.6901 0.2004 -0.5418 0.038 Uiso 1 1 calc R
H8B H 0.6576 0.1509 -0.4223 0.038 Uiso 1 1 calc R
C9 C 0.9013(6) 0.1700(4) -0.4346(4) 0.0409(13) Uani 1 1 d .
H9A H 0.9149 0.1058 -0.4672 0.061 Uiso 1 1 calc R
H9B H 0.9358 0.1687 -0.3508 0.061 Uiso 1 1 calc R
H9C H 0.9676 0.2165 -0.4713 0.061 Uiso 1 1 calc R
C10 C 0.9345(5) 0.0241(3) 0.1789(3) 0.0175(10) Uani 1 1 d .
H10A H 0.9931 -0.0315 0.1505 0.021 Uiso 1 1 calc R
H10B H 1.0129 0.0600 0.2341 0.021 Uiso 1 1 calc R
C11 C 0.8031(5) -0.0144(3) 0.2444(4) 0.0255(12) Uani 1 1 d .
H11A H 0.7274 -0.0548 0.1926 0.031 Uiso 1 1 calc R
H11B H 0.7409 0.0397 0.2725 0.031 Uiso 1 1 calc R
C12 C 0.8805(5) -0.0745(3) 0.3478(4) 0.0252(11) Uani 1 1 d .
H12A H 0.9512 -0.1244 0.3195 0.030 Uiso 1 1 calc R
H12B H 0.9495 -0.0322 0.4021 0.030 Uiso 1 1 calc R
C13 C 0.7549(6) -0.1230(4) 0.4124(4) 0.0433(14) Uani 1 1 d .
H13A H 0.8098 -0.1592 0.4783 0.065 Uiso 1 1 calc R
H13B H 0.6892 -0.1671 0.3600 0.065 Uiso 1 1 calc R
H13C H 0.6845 -0.0740 0.4407 0.065 Uiso 1 1 calc R
C14 C 1.0380(5) 0.1191(3) 0.0281(3) 0.0206(11) Uani 1 1 d .
H14A H 1.1085 0.1528 0.0903 0.025 Uiso 1 1 calc R
H14B H 1.0954 0.0597 0.0092 0.025 Uiso 1 1 calc R
C15 C 1.0184(5) 0.1827(3) -0.0780(4) 0.0245(11) Uani 1 1 d .
H15A H 0.9557 0.2409 -0.0625 0.029 Uiso 1 1 calc R
H15B H 0.9573 0.1477 -0.1437 0.029 Uiso 1 1 calc R
C16 C 1.1841(6) 0.2126(3) -0.1105(4) 0.0280(12) Uani 1 1 d .
H16A H 1.1678 0.2653 -0.1682 0.034 Uiso 1 1 calc R
H16B H 1.2497 0.2388 -0.0404 0.034 Uiso 1 1 calc R
C17 C 1.2806(6) 0.1329(4) -0.1598(4) 0.0359(12) Uani 1 1 d .
H17A H 1.3850 0.1585 -0.1769 0.054 Uiso 1 1 calc R
H17B H 1.2194 0.1081 -0.2312 0.054 Uiso 1 1 calc R
H17C H 1.2995 0.0806 -0.1030 0.054 Uiso 1 1 calc R
C18 C 0.7659(5) 0.0387(3) -0.0171(3) 0.0191(10) Uani 1 1 d .
H18A H 0.6688 0.0183 0.0182 0.023 Uiso 1 1 calc R
H18B H 0.7297 0.0857 -0.0790 0.023 Uiso 1 1 calc R
C19 C 0.8334(5) -0.0482(3) -0.0724(4) 0.0271(11) Uani 1 1 d .
H19A H 0.8725 -0.0955 -0.0114 0.032 Uiso 1 1 calc R
H19B H 0.9272 -0.0285 -0.1119 0.032 Uiso 1 1 calc R
C20 C 0.7045(5) -0.0958(4) -0.1607(3) 0.0283(11) Uani 1 1 d .
H20A H 0.7496 -0.1566 -0.1877 0.034 Uiso 1 1 calc R
H20B H 0.6095 -0.1126 -0.1210 0.034 Uiso 1 1 calc R
C21 C 0.6471(6) -0.0344(4) -0.2656(4) 0.0382(13) Uani 1 1 d .
H21A H 0.5645 -0.0696 -0.3168 0.057 Uiso 1 1 calc R
H21B H 0.7393 -0.0195 -0.3077 0.057 Uiso 1 1 calc R
H21C H 0.6004 0.0257 -0.2402 0.057 Uiso 1 1 calc R
C22 C 0.7873(5) 0.1765(3) 0.1130(4) 0.0219(10) Uani 1 1 d .
H22A H 0.7524 0.2163 0.0436 0.026 Uiso 1 1 calc R
H22B H 0.6881 0.1529 0.1431 0.026 Uiso 1 1 calc R
C23 C 0.8792(6) 0.2402(3) 0.2041(4) 0.0281(12) Uani 1 1 d .
H23A H 0.9772 0.2662 0.1744 0.034 Uiso 1 1 calc R
H23B H 0.9148 0.2016 0.2743 0.034 Uiso 1 1 calc R
C24 C 0.7724(6) 0.3233(3) 0.2356(4) 0.0298(12) Uani 1 1 d .
H24A H 0.7324 0.3595 0.1643 0.036 Uiso 1 1 calc R
H24B H 0.6769 0.2969 0.2681 0.036 Uiso 1 1 calc R
C25 C 0.8619(7) 0.3916(4) 0.3227(4) 0.0414(13) Uani 1 1 d .
H25A H 0.7878 0.4426 0.3416 0.062 Uiso 1 1 calc R
H25B H 0.9536 0.4204 0.2896 0.062 Uiso 1 1 calc R
H25C H 0.9021 0.3561 0.3934 0.062 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 114.13(17)
O1 S1 N1 113.8(2)
O2 S1 N1 113.66(19)
O1 S1 N2 110.32(17)
O2 S1 N2 106.58(17)
N1 S1 N2 96.58(19)
C7 O4 C8 115.1(4)
C1 N1 S1 110.2(3)
C7 N2 C2 131.9(3)
C7 N2 S1 120.6(3)
C2 N2 S1 107.1(3)
C18 N3 C14 110.9(3)
C18 N3 C22 105.5(3)
C14 N3 C22 112.4(3)
C18 N3 C10 111.7(3)
C14 N3 C10 105.6(3)
C22 N3 C10 110.8(3)
N1 C1 C2 116.1(4)
N1 C1 C6 124.8(4)
C2 C1 C6 119.0(4)
C3 C2 C1 121.6(4)
C3 C2 N2 129.7(4)
C1 C2 N2 108.6(3)
C2 C3 C4 118.4(5)
C5 C4 C3 120.2(5)
C4 C5 C6 121.7(5)
C5 C6 C1 119.0(5)
O3 C7 O4 125.9(4)
O3 C7 N2 122.2(4)
O4 C7 N2 111.9(4)
O4 C8 C9 111.5(4)
C11 C10 N3 117.0(3)
C10 C11 C12 109.3(3)
C13 C12 C11 112.5(4)
C15 C14 N3 116.2(3)
C14 C15 C16 110.6(4)
C17 C16 C15 115.4(4)
C19 C18 N3 116.0(3)
C18 C19 C20 111.3(4)
C21 C20 C19 114.7(4)
C23 C22 N3 115.3(4)
C22 C23 C24 110.6(4)
C25 C24 C23 112.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.434(3)
S1 O2 1.445(3)
S1 N1 1.555(4)
S1 N2 1.737(4)
O3 C7 1.200(5)
O4 C7 1.336(6)
O4 C8 1.452(6)
N1 C1 1.389(6)
N2 C7 1.389(6)
N2 C2 1.428(6)
N3 C18 1.526(5)
N3 C14 1.528(6)
N3 C22 1.528(6)
N3 C10 1.527(5)
C1 C2 1.390(7)
C1 C6 1.400(7)
C2 C3 1.389(7)
C3 C4 1.390(7)
C4 C5 1.373(7)
C5 C6 1.382(6)
C8 C9 1.511(7)
C10 C11 1.503(6)
C11 C12 1.536(6)
C12 C13 1.515(7)
C14 C15 1.509(6)
C15 C16 1.528(7)
C16 C17 1.519(7)
C18 C19 1.507(6)
C19 C20 1.537(6)
C20 C21 1.515(7)
C22 C23 1.510(6)
C23 C24 1.528(6)
C24 C25 1.513(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139040116
