#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:13:44 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301852 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/03/7060378.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_7060378
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         'C18 H15 N O4 S'
_chemical_formula_sum            'C18 H15 N O4 S'
_chemical_formula_weight         341.37
_chemical_name_common            'JK77C - Naphthyl-SO2-NH-C6H3(2-Me)(4-COOH)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                 101.281(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6257(9)
_cell_length_b                   14.7988(10)
_cell_length_c                   15.0858(10)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.2794
_cell_measurement_theta_min      2.2451
_cell_volume                     3202.1(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45692
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.394
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0300
_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)+(0.0404P)²+3.3812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                2863
_reflns_number_total             3264
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj06320g4.cif
_cod_data_source_block           Compound_A
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7060378--7060380.cif.
;
_cod_database_code               7060378
loop_
_space_group_symop_operation_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'
'-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_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
S S11 0.80269(2) 0.15933(2) 0.39094(2) 0.01481(10) Uani d . . . 1 . .
C C1 0.92182(9) 0.12944(9) 0.42183(9) 0.0168(3) Uani d . . . 1 . .
C C10 0.97963(10) 0.16555(9) 0.50144(9) 0.0178(3) Uani d . . . 1 . .
C C2 0.95463(11) 0.06831(10) 0.36747(10) 0.0227(3) Uani d . . . 1 . .
H H2 0.914291 0.045361 0.315226 0.027 Uiso calc U . R 1 . .
C C7 1.10393(12) 0.23047(14) 0.65445(12) 0.0372(4) Uani d . . . 1 . .
H H7 1.145408 0.252994 0.706162 0.045 Uiso calc U . R 1 . .
C C9 0.94993(10) 0.22824(10) 0.56069(9) 0.0202(3) Uani d . . . 1 . .
H H9 0.887093 0.248525 0.548861 0.024 Uiso calc U . R 1 . .
C C6 1.13461(11) 0.16956(13) 0.59919(12) 0.0340(4) Uani d . . . 1 . .
H H6 1.197489 0.149514 0.613183 0.041 Uiso calc U . R 1 . .
C C5 1.07450(10) 0.13564(11) 0.52134(10) 0.0238(3) Uani d . . . 1 . .
C C3 1.04847(11) 0.03931(11) 0.38900(11) 0.0281(4) Uani d . . . 1 . .
H H3 1.0712 -0.003179 0.351349 0.034 Uiso calc U . R 1 . .
C C8 1.01056(11) 0.26002(12) 0.63479(10) 0.0283(4) Uani d . . . 1 . .
H H8 0.989482 0.302542 0.673499 0.034 Uiso calc U . R 1 . .
C C4 1.10605(11) 0.07233(11) 0.46363(11) 0.0284(4) Uani d . . . 1 . .
H H4 1.169007 0.052487 0.477456 0.034 Uiso calc U . R 1 . .
O O12 0.75960(7) 0.15118(7) 0.46844(6) 0.0187(2) Uani d . . . 1 . .
O O13 0.76411(7) 0.11062(7) 0.31065(7) 0.0227(2) Uani d . . . 1 . .
N N14 0.79864(8) 0.26705(8) 0.36745(8) 0.0146(2) Uani d . . . 1 . .
C C16 0.83750(9) 0.40382(9) 0.29583(9) 0.0148(3) Uani d . . . 1 . .
C C17 0.87377(9) 0.44578(9) 0.22785(9) 0.0160(3) Uani d . . . 1 . .
H H17 0.87718 0.509866 0.226641 0.019 Uiso calc U . R 1 . .
C C18 0.90528(9) 0.39585(9) 0.16139(9) 0.0156(3) Uani d . . . 1 . .
C C15 0.83470(9) 0.30901(9) 0.29699(8) 0.0135(3) Uani d . . . 1 . .
C C19 0.89999(9) 0.30235(10) 0.16245(9) 0.0166(3) Uani d . . . 1 . .
H H19 0.920498 0.26812 0.116761 0.02 Uiso calc U . R 1 . .
C C20 0.86491(9) 0.25856(10) 0.22990(9) 0.0164(3) Uani d . . . 1 . .
H H20 0.861426 0.194469 0.230493 0.02 Uiso calc U . R 1 . .
C C21 0.80142(10) 0.45927(10) 0.36543(10) 0.0207(3) Uani d . . . 1 . .
H H21A 0.807438 0.523654 0.352498 0.031 Uiso calc U . R 1 . .
H H21B 0.837689 0.445506 0.425684 0.031 Uiso calc U . R 1 . .
H H21C 0.735676 0.444702 0.363376 0.031 Uiso calc U . R 1 . .
C C22 0.94566(9) 0.44253(10) 0.09122(9) 0.0177(3) Uani d . . . 1 . .
O O23 0.95683(7) 0.52703(7) 0.09512(7) 0.0250(2) Uani d . . . 1 . .
O O24 0.96781(8) 0.39306(8) 0.02914(7) 0.0271(3) Uani d . . D 1 . .
H H14 0.7898(12) 0.2991(13) 0.4118(13) 0.028(5) Uiso d . . . 1 . .
H H24 0.991(3) 0.422(3) -0.012(2) 0.149(15) Uiso d . . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O13 S11 O12 . . 118.96(6) ?
O13 S11 N14 . . 108.51(6) ?
O12 S11 N14 . . 104.81(6) ?
O13 S11 C1 . . 107.62(7) ?
O12 S11 C1 . . 109.31(6) ?
N14 S11 C1 . . 107.07(6) ?
C2 C1 C10 . . 122.06(13) ?
C2 C1 S11 . . 116.73(11) ?
C10 C1 S11 . . 121.18(10) ?
C9 C10 C1 . . 124.86(13) ?
C9 C10 C5 . . 118.37(13) ?
C1 C10 C5 . . 116.76(13) ?
C1 C2 C3 . . 120.07(15) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C6 C7 C8 . . 119.88(16) ?
C6 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C8 C9 C10 . . 120.81(14) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C7 C6 C5 . . 121.16(15) ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C5 C4 . . 121.39(14) ?
C6 C5 C10 . . 118.95(14) ?
C4 C5 C10 . . 119.65(14) ?
C4 C3 C2 . . 119.86(14) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C9 C8 C7 . . 120.81(15) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C3 C4 C5 . . 121.59(14) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C15 N14 S11 . . 125.97(10) ?
C15 N14 H14 . . 118.8(13) ?
S11 N14 H14 . . 112.2(13) ?
C17 C16 C15 . . 118.16(12) ?
C17 C16 C21 . . 120.47(12) ?
C15 C16 C21 . . 121.36(12) ?
C16 C17 C18 . . 121.42(13) ?
C16 C17 H17 . . 119.3 ?
C18 C17 H17 . . 119.3 ?
C19 C18 C17 . . 119.59(12) ?
C19 C18 C22 . . 120.33(12) ?
C17 C18 C22 . . 120.07(13) ?
C20 C15 C16 . . 120.73(12) ?
C20 C15 N14 . . 121.70(12) ?
C16 C15 N14 . . 117.56(12) ?
C18 C19 C20 . . 120.29(13) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C19 C20 C15 . . 119.78(13) ?
C19 C20 H20 . . 120.1 ?
C15 C20 H20 . . 120.1 ?
C16 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C16 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O23 C22 O24 . . 123.54(13) ?
O23 C22 C18 . . 119.71(12) ?
O24 C22 C18 . . 116.74(13) ?
C22 O24 H24 . . 116.(3) ?
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
S11 O13 . 1.4276(10) ?
S11 O12 . 1.4376(10) ?
S11 N14 . 1.6316(12) ?
S11 C1 . 1.7694(14) ?
C1 C2 . 1.369(2) ?
C1 C10 . 1.430(2) ?
C10 C9 . 1.414(2) ?
C10 C5 . 1.431(2) ?
C2 C3 . 1.414(2) ?
C2 H2 . 0.95 ?
C7 C6 . 1.362(3) ?
C7 C8 . 1.409(2) ?
C7 H7 . 0.95 ?
C9 C8 . 1.367(2) ?
C9 H9 . 0.95 ?
C6 C5 . 1.414(2) ?
C6 H6 . 0.95 ?
C5 C4 . 1.416(2) ?
C3 C4 . 1.358(2) ?
C3 H3 . 0.95 ?
C8 H8 . 0.95 ?
C4 H4 . 0.95 ?
N14 C15 . 1.4188(16) ?
N14 H14 . 0.851(19) ?
C16 C17 . 1.3898(18) ?
C16 C15 . 1.4040(19) ?
C16 C21 . 1.5070(18) ?
C17 C18 . 1.3945(19) ?
C17 H17 . 0.95 ?
C18 C19 . 1.386(2) ?
C18 C22 . 1.4804(18) ?
C15 C20 . 1.3970(19) ?
C19 C20 . 1.3868(18) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 O23 . 1.2610(18) ?
C22 O24 . 1.2793(17) ?
O24 H24 . 0.880(19) ?
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
C20 H20 O13 . 0.95 2.39 3.0255(17) 124.2 ?
N14 H14 O12 7_656 0.851(19) 2.20(2) 3.0240(15) 163.3(17) ?
O24 H24 O23 5_765 0.880(19) 1.755(19) 2.6335(14) 176.(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
O13 S11 C1 C2 . . . . -0.34(13) ?
O12 S11 C1 C2 . . . . 130.16(11) ?
N14 S11 C1 C2 . . . . -116.83(11) ?
O13 S11 C1 C10 . . . . -178.40(11) ?
O12 S11 C1 C10 . . . . -47.89(13) ?
N14 S11 C1 C10 . . . . 65.11(12) ?
C2 C1 C10 C9 . . . . -179.52(13) ?
S11 C1 C10 C9 . . . . -1.57(19) ?
C2 C1 C10 C5 . . . . 0.8(2) ?
S11 C1 C10 C5 . . . . 178.76(10) ?
C10 C1 C2 C3 . . . . -0.4(2) ?
S11 C1 C2 C3 . . . . -178.39(11) ?
C1 C10 C9 C8 . . . . -179.17(14) ?
C5 C10 C9 C8 . . . . 0.5(2) ?
C8 C7 C6 C5 . . . . 0.6(3) ?
C7 C6 C5 C4 . . . . 179.97(17) ?
C7 C6 C5 C10 . . . . -0.7(3) ?
C9 C10 C5 C6 . . . . 0.1(2) ?
C1 C10 C5 C6 . . . . 179.82(14) ?
C9 C10 C5 C4 . . . . 179.50(14) ?
C1 C10 C5 C4 . . . . -0.8(2) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C10 C9 C8 C7 . . . . -0.6(2) ?
C6 C7 C8 C9 . . . . 0.0(3) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
C6 C5 C4 C3 . . . . 179.74(15) ?
C10 C5 C4 C3 . . . . 0.4(2) ?
O13 S11 N14 C15 . . . . -53.37(12) ?
O12 S11 N14 C15 . . . . 178.56(11) ?
C1 S11 N14 C15 . . . . 62.53(12) ?
C15 C16 C17 C18 . . . . 1.06(19) ?
C21 C16 C17 C18 . . . . -178.30(13) ?
C16 C17 C18 C19 . . . . 0.4(2) ?
C16 C17 C18 C22 . . . . -178.51(12) ?
C17 C16 C15 C20 . . . . -1.97(19) ?
C21 C16 C15 C20 . . . . 177.39(12) ?
C17 C16 C15 N14 . . . . 179.19(11) ?
C21 C16 C15 N14 . . . . -1.46(19) ?
S11 N14 C15 C20 . . . . 10.75(18) ?
S11 N14 C15 C16 . . . . -170.42(10) ?
C17 C18 C19 C20 . . . . -1.0(2) ?
C22 C18 C19 C20 . . . . 177.93(12) ?
C18 C19 C20 C15 . . . . 0.1(2) ?
C16 C15 C20 C19 . . . . 1.4(2) ?
N14 C15 C20 C19 . . . . -179.77(12) ?
C19 C18 C22 O23 . . . . -174.43(13) ?
C17 C18 C22 O23 . . . . 4.5(2) ?
C19 C18 C22 O24 . . . . 5.32(19) ?
C17 C18 C22 O24 . . . . -175.80(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 138961483
