#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/92/2019264.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019264
loop_
_publ_author_name
'Jacobs, Danielle L.'
'Chan, Benny C.'
'O'Connor, Abby R.'
_publ_section_title
;
 N-[2-(Pyridin-2-yl)ethyl]-derivatives of methane-, benzene- and
 toluenesulfonamide: prospective ligands for metal coordination
;
_journal_coeditor_code           YP3050
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1397
_journal_page_last               1401
_journal_paper_doi               10.1107/S0108270113025341
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C8 H12 N2 O2 S'
_chemical_formula_moiety         'C8 H12 N2 O2 S'
_chemical_formula_sum            'C8 H12 N2 O2 S'
_chemical_formula_weight         200.27
_chemical_name_common
N-(2-(pyridin-2-yl)ethyl)methanesulfonamide
_chemical_name_systematic
;
N-[2-(pyridin-2-yl)ethyl]methanesulfonamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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           'APEX2 v2010.1-2'
_cell_angle_alpha                90
_cell_angle_beta                 93.284(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9122(16)
_cell_length_b                   5.0428(7)
_cell_length_c                   17.279(3)
_cell_measurement_reflns_used    128
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.9799
_cell_measurement_theta_min      4.2873
_cell_volume                     949.3(3)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'Instrument Service (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10388
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.58
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.8220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.384
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0475P)²+0.4601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                1765
_reflns_number_total             2277
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yp3050.cif
_cod_data_source_block           I
_cod_original_cell_volume        949.3(2)
_cod_database_code               2019264
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.65785(4) 0.90289(9) 0.34718(2) 0.01895(14) Uani d . 1
O O1 0.76528(11) 1.0283(3) 0.38274(7) 0.0266(3) Uani d . 1
O O2 0.56856(12) 1.0654(2) 0.30516(7) 0.0233(3) Uani d . 1
C C8 0.70704(17) 0.6598(4) 0.28261(11) 0.0246(4) Uani d . 1
H H8A 0.6357 0.5627 0.2602 0.037 Uiso calc R 1
H H8B 0.7628 0.5361 0.3106 0.037 Uiso calc R 1
H H8C 0.75 0.7455 0.241 0.037 Uiso calc R 1
N N1 0.59124(14) 0.7524(3) 0.41476(9) 0.0211(3) Uani d . 1
H H1 0.6386(19) 0.690(4) 0.4470(13) 0.025 Uiso d . 1
C C1 0.47383(15) 0.6144(4) 0.39803(10) 0.0199(4) Uani d . 1
H H1A 0.4756 0.4409 0.4249 0.024 Uiso calc R 1
H H1B 0.4624 0.5812 0.3416 0.024 Uiso calc R 1
C C2 0.36621(16) 0.7782(4) 0.42458(11) 0.0228(4) Uani d . 1
H H2A 0.381 0.8241 0.48 0.027 Uiso calc R 1
H H2B 0.3604 0.9455 0.3946 0.027 Uiso calc R 1
C C3 0.24739(16) 0.6291(4) 0.41358(10) 0.0209(4) Uani d . 1
C C4 0.16047(17) 0.6880(4) 0.35419(11) 0.0279(4) Uani d . 1
H H4 0.1748 0.8274 0.3188 0.033 Uiso calc R 1
C C5 0.05307(18) 0.5430(4) 0.34681(12) 0.0311(5) Uani d . 1
H H5 -0.0073 0.5826 0.3067 0.037 Uiso calc R 1
C C6 0.03450(17) 0.3408(4) 0.39810(12) 0.0293(5) Uani d . 1
H H6 -0.0387 0.2386 0.3945 0.035 Uiso calc R 1
C C7 0.12578(17) 0.2904(4) 0.45532(11) 0.0269(4) Uani d . 1
H H7 0.1137 0.1497 0.4906 0.032 Uiso calc R 1
N N2 0.23014(14) 0.4298(3) 0.46339(9) 0.0228(4) Uani d . 1
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
O2 S1 O1 118.52(8)
O2 S1 N1 108.39(8)
O1 S1 N1 106.83(8)
O2 S1 C8 107.39(8)
O1 S1 C8 107.81(9)
N1 S1 C8 107.43(9)
S1 C8 H8A 109.5
S1 C8 H8B 109.5
H8A C8 H8B 109.5
S1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C1 N1 S1 120.46(12)
C1 N1 H1 118.2(16)
S1 N1 H1 112.9(16)
N1 C1 C2 111.16(15)
N1 C1 H1A 109.4
C2 C1 H1A 109.4
N1 C1 H1B 109.4
C2 C1 H1B 109.4
H1A C1 H1B 108.0
C3 C2 C1 111.36(15)
C3 C2 H2A 109.4
C1 C2 H2A 109.4
C3 C2 H2B 109.4
C1 C2 H2B 109.4
H2A C2 H2B 108.0
N2 C3 C4 121.23(17)
N2 C3 C2 116.45(16)
C4 C3 C2 122.30(17)
C5 C4 C3 119.66(18)
C5 C4 H4 120.2
C3 C4 H4 120.2
C6 C5 C4 119.29(18)
C6 C5 H5 120.4
C4 C5 H5 120.4
C5 C6 C7 118.02(18)
C5 C6 H6 121.0
C7 C6 H6 121.0
N2 C7 C6 123.39(18)
N2 C7 H7 118.3
C6 C7 H7 118.3
C7 N2 C3 118.40(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4377(13)
S1 O1 1.4384(13)
S1 N1 1.6016(16)
S1 C8 1.7618(19)
C8 H8A 0.98
C8 H8B 0.98
C8 H8C 0.98
N1 C1 1.472(2)
N1 H1 0.80(2)
C1 C2 1.528(2)
C1 H1A 0.99
C1 H1B 0.99
C2 C3 1.502(2)
C2 H2A 0.99
C2 H2B 0.99
C3 N2 1.343(2)
C3 C4 1.389(3)
C4 C5 1.381(3)
C4 H4 0.95
C5 C6 1.373(3)
C5 H5 0.95
C6 C7 1.386(3)
C6 H6 0.95
C7 N2 1.339(2)
C7 H7 0.95
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
O2 S1 N1 C1 48.03(16)
O1 S1 N1 C1 176.81(14)
C8 S1 N1 C1 -67.72(16)
S1 N1 C1 C2 -102.11(16)
N1 C1 C2 C3 -175.37(15)
C1 C2 C3 N2 73.6(2)
C1 C2 C3 C4 -105.0(2)
N2 C3 C4 C5 1.3(3)
C2 C3 C4 C5 179.71(18)
C3 C4 C5 C6 -0.5(3)
C4 C5 C6 C7 -0.3(3)
C5 C6 C7 N2 0.6(3)
C6 C7 N2 C3 0.1(3)
C4 C3 N2 C7 -1.0(3)
C2 C3 N2 C7 -179.55(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 51172552
