#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:13:44 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301852 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/03/7060379.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_7060379
loop_
_publ_author_name
'Li, Edward W.'
'Katinas, Jade'
'Jones, Marjorie A.'
'Hamaker, Christopher G.'
_publ_section_title
;
 Structural characterization of naphthalene sulfonamides and a sulfonate
 ester and their in vitro efficacy against Leishmania tarentolae
 promastigotes
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4791
_journal_page_last               4801
_journal_paper_doi               10.1039/D0NJ06320G
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C16 H12 Cl N O2 S'
_chemical_formula_sum            'C16 H12 Cl N O2 S'
_chemical_formula_weight         317.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2019-05-21 deposited with the CCDC.	2021-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.508(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.923(2)
_cell_length_b                   9.1409(8)
_cell_length_c                   17.8901(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      13.14
_cell_measurement_theta_min      7.23
_cell_measurement_wavelength     0.71073
_cell_volume                     1446.7(4)
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.04957
_diffrn_orient_matrix_UB_12      -0.088154
_diffrn_orient_matrix_UB_13      -0.018992
_diffrn_orient_matrix_UB_21      -0.057232
_diffrn_orient_matrix_UB_22      0.015781
_diffrn_orient_matrix_UB_23      -0.05126
_diffrn_orient_matrix_UB_31      0.083937
_diffrn_orient_matrix_UB_32      0.062839
_diffrn_orient_matrix_UB_33      -0.013806
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0095
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3522
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.30
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        -3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.8311
_exptl_absorpt_correction_T_min  0.8136
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   3
        Theta correction was applied.
        Averaged transmission function was used.
        No Fourier smoothing was applied.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0534P)²+0.3885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                2683
_reflns_number_total             3317
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj06320g4.cif
_cod_data_source_block           Compound_B
_cod_depositor_comments
'Adding full bibliography for 7060378--7060380.cif.'
_cod_database_code               7060379
loop_
_space_group_symop_operation_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_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.21897(18) 0.04499(19) 0.38612(9) 0.0457(4) Uani d . . . 1 . .
C C2 0.1261(2) -0.0717(2) 0.39446(13) 0.0587(5) Uani d . . . 1 . .
H H2 0.069044 -0.11277 0.35246 0.07 Uiso calc U . R 1 . .
C C3 0.1173(3) -0.1293(2) 0.46686(15) 0.0739(6) Uani d . . . 1 . .
H H3 0.054781 -0.208876 0.472532 0.089 Uiso calc U . R 1 . .
C C4 0.1989(3) -0.0697(3) 0.52760(14) 0.0780(7) Uani d . . . 1 . .
H H4 0.191246 -0.108915 0.574935 0.094 Uiso calc U . R 1 . .
C C5 0.2960(3) 0.0508(2) 0.52186(11) 0.0642(6) Uani d . . . 1 . .
C C6 0.3848(4) 0.1130(4) 0.58601(12) 0.0884(9) Uani d . . . 1 . .
H H6 0.377586 0.074318 0.63348 0.106 Uiso calc U . R 1 . .
C C7 0.4785(3) 0.2259(4) 0.57984(13) 0.0891(9) Uani d . . . 1 . .
H H7 0.535108 0.264493 0.622643 0.107 Uiso calc U . R 1 . .
C C8 0.4907(3) 0.2854(3) 0.50903(13) 0.0762(7) Uani d . . . 1 . .
H H8 0.55598 0.363545 0.505041 0.091 Uiso calc U . R 1 . .
C C9 0.4081(2) 0.2303(2) 0.44536(11) 0.0586(5) Uani d . . . 1 . .
H H9 0.417573 0.271757 0.398731 0.07 Uiso calc U . R 1 . .
C C10 0.3086(2) 0.1114(2) 0.44966(9) 0.0495(4) Uani d . . . 1 . .
C C16 -0.0230(2) 0.4138(2) 0.35849(10) 0.0512(4) Uani d . . . 1 . .
C C17 -0.1683(3) 0.4526(3) 0.37118(13) 0.0697(6) Uani d . . . 1 . .
H H17 -0.182574 0.527298 0.40483 0.084 Uiso calc U . R 1 . .
C C18 -0.2904(2) 0.3802(3) 0.33386(15) 0.0757(7) Uani d . . . 1 . .
H H18 -0.38768 0.406428 0.341871 0.091 Uiso calc U . R 1 . .
C C19 -0.2692(2) 0.2686(3) 0.28452(14) 0.0689(6) Uani d . . . 1 . .
H H19 -0.352196 0.217985 0.260445 0.083 Uiso calc U . R 1 . .
C C20 -0.12493(19) 0.2315(2) 0.27059(11) 0.0527(4) Uani d . . . 1 . .
H H20 -0.111754 0.157203 0.236543 0.063 Uiso calc U . R 1 . .
C C15 0.00030(17) 0.30458(17) 0.30716(8) 0.0407(3) Uani d . . . 1 . .
Cl Cl21 0.13048(7) 0.50473(7) 0.40704(3) 0.0786(2) Uani d . . . 1 . .
N N14 0.14805(15) 0.27456(16) 0.29002(8) 0.0427(3) Uani d . . . 1 . .
O O12 0.37706(13) 0.13394(16) 0.28022(7) 0.0579(3) Uani d . . . 1 . .
O O13 0.13053(14) 0.01777(14) 0.24303(7) 0.0564(3) Uani d . . . 1 . .
S S11 0.22443(4) 0.11132(5) 0.29367(2) 0.04242(12) Uani d . . . 1 . .
H H14 0.210(2) 0.336(2) 0.2973(12) 0.059(6) Uiso 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'
Cl Cl 0.1484 0.1585 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 2 -4
-3 4 1
0 3 -7
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 121.64(17) ?
C2 C1 S11 . . 117.37(14) ?
C10 C1 S11 . . 120.99(14) ?
C1 C2 C3 . . 119.9(2) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 122.0(2) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C4 C5 C10 . . 119.4(2) ?
C4 C5 C6 . . 122.3(2) ?
C10 C5 C6 . . 118.3(2) ?
C7 C6 C5 . . 121.8(2) ?
C7 C6 H6 . . 119.1 ?
C5 C6 H6 . . 119.1 ?
C6 C7 C8 . . 119.9(2) ?
C6 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C9 C8 C7 . . 120.9(3) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 120.8(2) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C9 C10 C5 . . 118.28(18) ?
C9 C10 C1 . . 124.83(17) ?
C5 C10 C1 . . 116.88(19) ?
C17 C16 C15 . . 120.93(19) ?
C17 C16 Cl21 . . 119.20(17) ?
C15 C16 Cl21 . . 119.86(14) ?
C18 C17 C16 . . 119.7(2) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C17 C18 C19 . . 120.18(19) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C18 C19 C20 . . 120.3(2) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C15 . . 120.4(2) ?
C19 C20 H20 . . 119.8 ?
C15 C20 H20 . . 119.8 ?
C20 C15 C16 . . 118.39(16) ?
C20 C15 N14 . . 121.19(16) ?
C16 C15 N14 . . 120.35(15) ?
C15 N14 S11 . . 124.13(12) ?
C15 N14 H14 . . 118.5(16) ?
S11 N14 H14 . . 111.5(16) ?
O12 S11 O13 . . 118.11(8) ?
O12 S11 N14 . . 105.21(8) ?
O13 S11 N14 . . 108.20(7) ?
O12 S11 C1 . . 110.52(8) ?
O13 S11 C1 . . 107.53(9) ?
N14 S11 C1 . . 106.71(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.371(3) ?
C1 C10 . 1.436(2) ?
C1 S11 . 1.7682(17) ?
C2 C3 . 1.410(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.342(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.414(4) ?
C4 H4 . 0.93 ?
C5 C10 . 1.423(3) ?
C5 C6 . 1.425(3) ?
C6 C7 . 1.342(4) ?
C6 H6 . 0.93 ?
C7 C8 . 1.396(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.370(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.412(3) ?
C9 H9 . 0.93 ?
C16 C17 . 1.391(3) ?
C16 C15 . 1.391(2) ?
C16 Cl21 . 1.735(2) ?
C17 C18 . 1.371(4) ?
C17 H17 . 0.93 ?
C18 C19 . 1.378(4) ?
C18 H18 . 0.93 ?
C19 C20 . 1.385(3) ?
C19 H19 . 0.93 ?
C20 C15 . 1.390(2) ?
C20 H20 . 0.93 ?
C15 N14 . 1.419(2) ?
N14 S11 . 1.6382(15) ?
N14 H14 . 0.78(2) ?
O12 S11 . 1.4287(13) ?
O13 S11 . 1.4337(12) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N14 H14 O13 2 0.78(2) 2.36(2) 3.0824(19) 153.(2) ?
C19 H19 O12 1_455 0.93 2.6 3.380(2) 141.4 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . -0.1(3) ?
S11 C1 C2 C3 . . . . 179.93(15) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
C3 C4 C5 C10 . . . . -0.1(3) ?
C3 C4 C5 C6 . . . . -178.9(2) ?
C4 C5 C6 C7 . . . . 178.9(2) ?
C10 C5 C6 C7 . . . . 0.1(3) ?
C5 C6 C7 C8 . . . . 0.0(4) ?
C6 C7 C8 C9 . . . . 0.1(4) ?
C7 C8 C9 C10 . . . . -0.3(3) ?
C8 C9 C10 C5 . . . . 0.3(3) ?
C8 C9 C10 C1 . . . . -179.13(17) ?
C4 C5 C10 C9 . . . . -179.08(17) ?
C6 C5 C10 C9 . . . . -0.2(3) ?
C4 C5 C10 C1 . . . . 0.4(2) ?
C6 C5 C10 C1 . . . . 179.27(16) ?
C2 C1 C10 C9 . . . . 179.13(17) ?
S11 C1 C10 C9 . . . . -0.9(2) ?
C2 C1 C10 C5 . . . . -0.3(2) ?
S11 C1 C10 C5 . . . . 179.68(12) ?
C15 C16 C17 C18 . . . . 1.4(3) ?
Cl21 C16 C17 C18 . . . . -179.15(16) ?
C16 C17 C18 C19 . . . . 0.6(3) ?
C17 C18 C19 C20 . . . . -1.8(3) ?
C18 C19 C20 C15 . . . . 1.1(3) ?
C19 C20 C15 C16 . . . . 0.8(2) ?
C19 C20 C15 N14 . . . . -175.89(16) ?
C17 C16 C15 C20 . . . . -2.1(3) ?
Cl21 C16 C15 C20 . . . . 178.46(12) ?
C17 C16 C15 N14 . . . . 174.65(16) ?
Cl21 C16 C15 N14 . . . . -4.8(2) ?
C20 C15 N14 S11 . . . . -55.13(19) ?
C16 C15 N14 S11 . . . . 128.19(15) ?
C15 N14 S11 O12 . . . . -173.98(13) ?
C15 N14 S11 O13 . . . . 58.91(15) ?
C15 N14 S11 C1 . . . . -56.54(14) ?
C2 C1 S11 O12 . . . . -133.54(14) ?
C10 C1 S11 O12 . . . . 46.48(15) ?
C2 C1 S11 O13 . . . . -3.31(16) ?
C10 C1 S11 O13 . . . . 176.70(12) ?
C2 C1 S11 N14 . . . . 112.59(14) ?
C10 C1 S11 N14 . . . . -67.40(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 51703110
