#------------------------------------------------------------------------------
#$Date: 2025-08-21 12:25:49 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301846 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/69/7006936.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_7006936
loop_
_publ_author_name
'Squires, Clare'
'Baxter, Christopher W.'
'Campbell, John'
'Lindoy, Leonard F.'
'McNab, Hamish'
'Parkin, Andrew'
'Parsons, Simon'
'Tasker, Peter A.'
'Wei, Gang'
'White, David J.'
_publ_section_title
;
 Design of base metal extractants. Part 1. Inter-ligand hydrogen
 bonding in the assembly of pseudo-macrocyclic
 bis(aminosulfonamidato)M(II) complexes.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2026
_journal_page_last               2034
_journal_paper_doi               10.1039/b515650p
_journal_year                    2006
_chemical_formula_moiety         'C17 H22 N2 O2 S'
_chemical_formula_sum            'C17 H22 N2 O2 S'
_chemical_formula_weight         318.43
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_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            4
_cell_length_a                   22.113(3)
_cell_length_b                   8.4446(14)
_cell_length_c                   8.9661(8)
_cell_measurement_reflns_used    122
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      12
_cell_volume                     1674.3(4)
_computing_cell_refinement       'Stoe DIF4'
_computing_data_collection       'Stoe DIF4'
_computing_data_reduction        'Stoe REDU4'
_computing_molecular_graphics    SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe Stadi-4 4-circle diffractometer'
_diffrn_measurement_method       Omega-theta
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3525
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.89
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(17)
_refine_ls_extinction_coef       0.0038(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         1770
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0539
_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)+(0.0413P)²+0.0087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                1169
_reflns_number_total             1770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b515650p.txt
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7006936
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
C1A C 0.3263(2) 0.7670(6) 0.3465(5) 0.0288(15) Uani 1 1 d . . .
S2A S 0.36745(6) 0.94188(18) 0.31019(17) 0.0318(3) Uani 1 1 d . . .
O1A O 0.32537(14) 1.0706(4) 0.3133(6) 0.0426(9) Uani 1 1 d . . .
O2A O 0.40235(18) 0.9124(5) 0.1770(4) 0.0408(12) Uani 1 1 d . . .
N3A N 0.41647(19) 0.9696(6) 0.4406(5) 0.0284(13) Uani 1 1 d D . .
H3A H 0.4537(13) 0.906(5) 0.434(6) 0.034 Uiso 1 1 d D . .
C4A C 0.3956(2) 1.0080(7) 0.5932(6) 0.0350(15) Uani 1 1 d . . .
H4AA H 0.3875 0.9100 0.6483 0.042 Uiso 1 1 calc R . .
H4BA H 0.3580 1.0693 0.5883 0.042 Uiso 1 1 calc R . .
C5A C 0.4437(2) 1.1027(7) 0.6727(5) 0.0307(15) Uani 1 1 d . . .
H5AA H 0.4505 1.2020 0.6188 0.037 Uiso 1 1 calc R . .
H5BA H 0.4817 1.0429 0.6721 0.037 Uiso 1 1 calc R . .
C6A C 0.4263(2) 1.1399(7) 0.8332(6) 0.0338(16) Uani 1 1 d . . .
H6AA H 0.3887 1.2013 0.8344 0.041 Uiso 1 1 calc R . .
H6BA H 0.4192 1.0409 0.8875 0.041 Uiso 1 1 calc R . .
N7A N 0.47412(19) 1.2300(6) 0.9073(5) 0.0304(12) Uani 1 1 d D . .
H7A H 0.4818(19) 1.326(4) 0.849(5) 0.036 Uiso 1 1 d D . .
C8A C 0.4559(2) 1.2803(7) 1.0590(5) 0.0334(16) Uani 1 1 d . . .
H8AA H 0.4372 1.1909 1.1112 0.040 Uiso 1 1 calc R . .
H8BA H 0.4257 1.3651 1.0515 0.040 Uiso 1 1 calc R . .
C9A C 0.5093(3) 1.3384(7) 1.1470(6) 0.0328(15) Uani 1 1 d . . .
C10A C 0.5142(2) 1.2908(7) 1.2962(7) 0.0382(15) Uani 1 1 d . . .
H10A H 0.4833 1.2299 1.3396 0.046 Uiso 1 1 calc R . .
C11A C 0.5638(3) 1.3324(8) 1.3797(7) 0.0492(18) Uani 1 1 d . . .
H11A H 0.5670 1.2985 1.4792 0.059 Uiso 1 1 calc R . .
C12A C 0.6088(2) 1.4231(7) 1.3185(8) 0.0451(16) Uani 1 1 d . . .
H12A H 0.6426 1.4515 1.3761 0.054 Uiso 1 1 calc R . .
C13A C 0.6045(3) 1.4731(7) 1.1717(7) 0.0420(16) Uani 1 1 d . . .
H13A H 0.6351 1.5361 1.1295 0.050 Uiso 1 1 calc R . .
C14A C 0.5545(2) 1.4292(7) 1.0876(6) 0.0355(15) Uani 1 1 d . . .
H14A H 0.5516 1.4626 0.9878 0.043 Uiso 1 1 calc R . .
C15A C 0.2764(2) 0.7729(8) 0.4404(6) 0.0394(16) Uani 1 1 d . . .
H15A H 0.2641 0.8694 0.4830 0.047 Uiso 1 1 calc R . .
C16A C 0.2450(2) 0.6353(8) 0.4705(7) 0.0430(17) Uani 1 1 d . . .
H16A H 0.2116 0.6382 0.5354 0.052 Uiso 1 1 calc R . .
C17A C 0.2622(2) 0.4915(7) 0.4057(7) 0.0402(16) Uani 1 1 d . . .
C18A C 0.3116(2) 0.4889(6) 0.3130(8) 0.0389(14) Uani 1 1 d . . .
H18A H 0.3236 0.3931 0.2686 0.047 Uiso 1 1 calc R . .
C19A C 0.3436(2) 0.6252(7) 0.2846(6) 0.0352(15) Uani 1 1 d . . .
H19A H 0.3777 0.6214 0.2221 0.042 Uiso 1 1 calc R . .
C20A C 0.2273(3) 0.3416(9) 0.4382(8) 0.066(2) Uani 1 1 d . . .
H20A H 0.1849 0.3671 0.4525 0.098 Uiso 1 1 calc R . .
H20B H 0.2431 0.2927 0.5280 0.098 Uiso 1 1 calc R . .
H20C H 0.2315 0.2690 0.3551 0.098 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
C19A C1A C15A 119.9(5) . . ?
C19A C1A S2A 120.7(4) . . ?
C15A C1A S2A 119.4(5) . . ?
O1A S2A O2A 119.7(3) . . ?
O1A S2A N3A 108.2(3) . . ?
O2A S2A N3A 105.4(2) . . ?
O1A S2A C1A 107.3(2) . . ?
O2A S2A C1A 106.5(3) . . ?
N3A S2A C1A 109.5(3) . . ?
C4A N3A S2A 119.6(3) . . ?
C4A N3A H3A 116(3) . . ?
S2A N3A H3A 116(3) . . ?
N3A C4A C5A 109.5(4) . . ?
N3A C4A H4AA 109.8 . . ?
C5A C4A H4AA 109.8 . . ?
N3A C4A H4BA 109.8 . . ?
C5A C4A H4BA 109.8 . . ?
H4AA C4A H4BA 108.2 . . ?
C4A C5A C6A 112.2(4) . . ?
C4A C5A H5AA 109.2 . . ?
C6A C5A H5AA 109.2 . . ?
C4A C5A H5BA 109.2 . . ?
C6A C5A H5BA 109.2 . . ?
H5AA C5A H5BA 107.9 . . ?
N7A C6A C5A 110.7(4) . . ?
N7A C6A H6AA 109.5 . . ?
C5A C6A H6AA 109.5 . . ?
N7A C6A H6BA 109.5 . . ?
C5A C6A H6BA 109.5 . . ?
H6AA C6A H6BA 108.1 . . ?
C6A N7A C8A 111.7(4) . . ?
C6A N7A H7A 108(3) . . ?
C8A N7A H7A 107(3) . . ?
N7A C8A C9A 111.2(4) . . ?
N7A C8A H8AA 109.4 . . ?
C9A C8A H8AA 109.4 . . ?
N7A C8A H8BA 109.4 . . ?
C9A C8A H8BA 109.4 . . ?
H8AA C8A H8BA 108.0 . . ?
C14A C9A C10A 118.4(5) . . ?
C14A C9A C8A 123.5(5) . . ?
C10A C9A C8A 118.0(5) . . ?
C11A C10A C9A 120.6(6) . . ?
C11A C10A H10A 119.7 . . ?
C9A C10A H10A 119.7 . . ?
C12A C11A C10A 120.3(6) . . ?
C12A C11A H11A 119.8 . . ?
C10A C11A H11A 119.8 . . ?
C11A C12A C13A 120.1(6) . . ?
C11A C12A H12A 119.9 . . ?
C13A C12A H12A 119.9 . . ?
C12A C13A C14A 119.3(6) . . ?
C12A C13A H13A 120.4 . . ?
C14A C13A H13A 120.4 . . ?
C9A C14A C13A 121.3(5) . . ?
C9A C14A H14A 119.3 . . ?
C13A C14A H14A 119.3 . . ?
C16A C15A C1A 119.2(6) . . ?
C16A C15A H15A 120.4 . . ?
C1A C15A H15A 120.4 . . ?
C15A C16A C17A 120.9(5) . . ?
C15A C16A H16A 119.6 . . ?
C17A C16A H16A 119.6 . . ?
C18A C17A C16A 118.8(6) . . ?
C18A C17A C20A 120.6(6) . . ?
C16A C17A C20A 120.6(5) . . ?
C17A C18A C19A 120.5(5) . . ?
C17A C18A H18A 119.7 . . ?
C19A C18A H18A 119.7 . . ?
C1A C19A C18A 120.7(5) . . ?
C1A C19A H19A 119.6 . . ?
C18A C19A H19A 119.6 . . ?
C17A C20A H20A 109.5 . . ?
C17A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C17A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 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
C1A C19A 1.374(7) . ?
C1A C15A 1.389(7) . ?
C1A S2A 1.765(5) . ?
S2A O1A 1.431(3) . ?
S2A O2A 1.443(4) . ?
S2A N3A 1.612(5) . ?
N3A C4A 1.479(7) . ?
N3A H3A 0.98(2) . ?
C4A C5A 1.509(7) . ?
C4A H4AA 0.9800 . ?
C4A H4BA 0.9800 . ?
C5A C6A 1.522(7) . ?
C5A H5AA 0.9800 . ?
C5A H5BA 0.9800 . ?
C6A N7A 1.462(6) . ?
C6A H6AA 0.9800 . ?
C6A H6BA 0.9800 . ?
N7A C8A 1.481(6) . ?
N7A H7A 0.98(2) . ?
C8A C9A 1.503(7) . ?
C8A H8AA 0.9800 . ?
C8A H8BA 0.9800 . ?
C9A C14A 1.368(8) . ?
C9A C10A 1.401(8) . ?
C10A C11A 1.374(8) . ?
C10A H10A 0.9400 . ?
C11A C12A 1.370(8) . ?
C11A H11A 0.9400 . ?
C12A C13A 1.385(9) . ?
C12A H12A 0.9400 . ?
C13A C14A 1.390(7) . ?
C13A H13A 0.9400 . ?
C14A H14A 0.9400 . ?
C15A C16A 1.380(8) . ?
C15A H15A 0.9400 . ?
C16A C17A 1.398(8) . ?
C16A H16A 0.9400 . ?
C17A C18A 1.373(8) . ?
C17A C20A 1.511(8) . ?
C18A C19A 1.375(7) . ?
C18A H18A 0.9400 . ?
C19A H19A 0.9400 . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C20A H20C 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21144607
2 PubChem 53466191
