#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:52:39 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/92/7059223.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_7059223
loop_
_publ_author_name
'Custodio, Jean M. F.'
'Moura, Andrea F.'
'de Moraes, Manoel O.'
'Perez, Caridad N.'
'Napolitano, Hamilton B.'
_publ_section_title
;
 On the in silico and in vitro anticancer activity of sulfonamide
 chalcones: potential JNKK3 inhibitors
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3294
_journal_page_last               3309
_journal_paper_doi               10.1039/C9NJ05612B
_journal_volume                  44
_journal_year                    2020
_chemical_formula_sum            'C21 H16 F N O3 S'
_chemical_formula_weight         381.41
_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'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc20qns6
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-04-02 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.278(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1059(5)
_cell_length_b                   17.5044(8)
_cell_length_c                   8.1948(4)
_cell_measurement_reflns_used    8438
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.80
_cell_volume                     1836.98(14)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.418
_diffrn_reflns_theta_min         1.590
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.647
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.213
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0285(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0486P)²+0.5715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2982
_reflns_number_total             3762
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj05612b2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
;Adding full bibliography for 7059220--7059228.cif.

 Adding full bibliography for 7059220--7059228.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7059223
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.878
_shelx_estimated_absorpt_t_max   0.957
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.33265(4) 0.02278(2) 0.32950(6) 0.05081(16) Uani 1 1 d . .
C16 C 0.25233(13) 0.02443(9) 0.1278(2) 0.0460(4) Uani 1 1 d . .
N1 N 0.41472(12) 0.09256(9) 0.3346(2) 0.0551(4) Uani 1 1 d . .
O2 O 0.39541(11) -0.04451(7) 0.34470(18) 0.0651(4) Uani 1 1 d . .
O3 O 0.26704(12) 0.03624(8) 0.44504(17) 0.0674(4) Uani 1 1 d . .
O1 O 0.58708(12) 0.11983(8) 0.2403(2) 0.0811(5) Uani 1 1 d . .
C6 C 0.81526(14) 0.25752(10) 0.0970(2) 0.0496(4) Uani 1 1 d . .
C21 C 0.29105(15) -0.00476(10) -0.0043(2) 0.0534(4) Uani 1 1 d . .
H21 H 0.357772 -0.025652 0.014450 0.064 Uiso 1 1 calc R U
F1 F 1.05484(12) 0.37191(9) -0.0479(2) 0.1022(5) Uani 1 1 d . .
C15 C 0.39291(13) 0.17123(9) 0.3122(2) 0.0459(4) Uani 1 1 d . .
C8 C 0.64241(14) 0.24065(10) 0.1765(2) 0.0524(4) Uani 1 1 d . .
H8 H 0.627751 0.292625 0.166066 0.063 Uiso 1 1 calc R U
C9 C 0.56649(14) 0.18863(10) 0.2278(2) 0.0514(4) Uani 1 1 d . .
C10 C 0.46832(13) 0.21918(9) 0.2641(2) 0.0455(4) Uani 1 1 d . .
C4 C 0.89457(17) 0.37524(12) 0.0350(3) 0.0648(5) Uani 1 1 d . .
H4 H 0.893568 0.428197 0.025587 0.078 Uiso 1 1 calc R U
C5 C 0.81358(15) 0.33667(11) 0.0820(2) 0.0560(5) Uani 1 1 d . .
C7 C 0.73066(15) 0.21474(11) 0.1452(2) 0.0546(4) Uani 1 1 d . .
C14 C 0.30106(15) 0.20251(11) 0.3414(2) 0.0593(5) Uani 1 1 d . .
H14 H 0.251656 0.171106 0.373762 0.071 Uiso 1 1 calc R U
C17 C 0.15280(15) 0.05512(12) 0.1005(3) 0.0617(5) Uani 1 1 d . .
H17 H 0.126476 0.074284 0.189099 0.074 Uiso 1 1 calc R U
C1 C 0.90088(16) 0.21840(12) 0.0647(3) 0.0659(5) Uani 1 1 d . .
H1A H 0.903430 0.165482 0.074987 0.079 Uiso 1 1 calc R U
C19 C 0.1320(2) 0.02802(12) -0.1909(3) 0.0723(6) Uani 1 1 d . .
C3 C 0.97644(16) 0.33357(14) 0.0025(3) 0.0672(6) Uani 1 1 d . .
C11 C 0.44652(16) 0.29753(11) 0.2492(3) 0.0605(5) Uani 1 1 d . .
H11 H 0.495537 0.330133 0.219393 0.073 Uiso 1 1 calc R U
C20 C 0.23007(19) -0.00259(11) -0.1631(3) 0.0636(5) Uani 1 1 d . .
C12 C 0.3552(2) 0.32765(12) 0.2772(3) 0.0739(6) Uani 1 1 d . .
C13 C 0.28271(18) 0.28013(12) 0.3226(3) 0.0710(6) Uani 1 1 d . .
H13 H 0.220495 0.300373 0.340876 0.085 Uiso 1 1 calc R U
C18 C 0.09300(18) 0.05689(13) -0.0605(3) 0.0742(6) Uani 1 1 d . .
H18 H 0.026194 0.077698 -0.080595 0.089 Uiso 1 1 calc R U
C2 C 0.98249(18) 0.25639(14) 0.0176(3) 0.0757(6) Uani 1 1 d . .
H2 H 1.039864 0.229837 -0.003191 0.091 Uiso 1 1 calc R U
H1 H 0.470(2) 0.0802(15) 0.316(3) 0.091 Uiso 1 1 d . U
H5 H 0.756(2) 0.3645(14) 0.097(3) 0.091 Uiso 1 1 d . U
H7 H 0.7417(19) 0.1597(15) 0.154(3) 0.091 Uiso 1 1 d . U
H19 H 0.092(2) 0.0288(14) -0.299(3) 0.091 Uiso 1 1 d . U
H20 H 0.2588(19) -0.0215(14) -0.251(3) 0.091 Uiso 1 1 d . U
H12 H 0.3431(19) 0.3827(14) 0.265(3) 0.091 Uiso 1 1 d . U
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.molstruc.2019.126896 2019
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O3 119.72(9)
O2 S1 N1 104.63(8)
O3 S1 N1 110.37(9)
O2 S1 C16 108.30(8)
O3 S1 C16 107.20(8)
N1 S1 C16 105.82(8)
C17 C16 C21 120.38(18)
C17 C16 S1 120.83(14)
C21 C16 S1 118.78(14)
C15 N1 S1 128.09(13)
C1 C6 C5 118.24(18)
C1 C6 C7 119.34(17)
C5 C6 C7 122.42(17)
C20 C21 C16 119.53(18)
C14 C15 N1 121.44(16)
C14 C15 C10 119.77(16)
N1 C15 C10 118.76(15)
C7 C8 C9 121.11(17)
O1 C9 C8 118.54(16)
O1 C9 C10 121.31(16)
C8 C9 C10 120.15(15)
C11 C10 C15 117.60(16)
C11 C10 C9 120.38(16)
C15 C10 C9 122.01(15)
C3 C4 C5 118.3(2)
C4 C5 C6 120.88(19)
C8 C7 C6 128.66(18)
C13 C14 C15 120.32(19)
C16 C17 C18 119.04(19)
C2 C1 C6 121.4(2)
C20 C19 C18 120.4(2)
C2 C3 F1 119.0(2)
C2 C3 C4 123.05(19)
F1 C3 C4 118.0(2)
C12 C11 C10 122.07(19)
C19 C20 C21 120.4(2)
C11 C12 C13 119.44(19)
C12 C13 C14 120.78(19)
C19 C18 C17 120.3(2)
C3 C2 C1 118.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4267(14)
S1 O3 1.4275(14)
S1 N1 1.6221(16)
S1 C16 1.7611(19)
C16 C17 1.384(3)
C16 C21 1.387(2)
N1 C15 1.411(2)
O1 C9 1.234(2)
C6 C1 1.387(3)
C6 C5 1.391(3)
C6 C7 1.460(3)
C21 C20 1.376(3)
F1 C3 1.363(2)
C15 C14 1.389(3)
C15 C10 1.415(2)
C8 C7 1.317(3)
C8 C9 1.474(2)
C9 C10 1.481(2)
C10 C11 1.401(2)
C4 C3 1.370(3)
C4 C5 1.380(3)
C14 C13 1.383(3)
C17 C18 1.385(3)
C1 C2 1.382(3)
C19 C20 1.367(3)
C19 C18 1.375(3)
C3 C2 1.358(3)
C11 C12 1.371(3)
C12 C13 1.372(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C20 H20 O1 0.94(3) 2.64(3) 3.317(3) 129.2(19) 3_655
C5 H5 O2 0.92(3) 2.67(3) 3.590(2) 174(2) 2_655
C20 H20 O3 0.94(3) 2.71(3) 3.416(2) 132.3(19) 1_554
C19 H19 F1 0.93(3) 2.64(3) 3.375(3) 136.0(19) 4_465
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 C16 C17 146.47(15)
O3 S1 C16 C17 16.00(17)
N1 S1 C16 C17 -101.80(16)
O2 S1 C16 C21 -34.35(15)
O3 S1 C16 C21 -164.82(13)
N1 S1 C16 C21 77.37(15)
O2 S1 N1 C15 174.99(16)
O3 S1 N1 C15 -54.96(19)
C16 S1 N1 C15 60.70(18)
C17 C16 C21 C20 0.4(3)
S1 C16 C21 C20 -178.77(14)
S1 N1 C15 C14 23.7(3)
S1 N1 C15 C10 -158.31(14)
C7 C8 C9 O1 -0.3(3)
C7 C8 C9 C10 179.33(18)
C14 C15 C10 C11 0.5(3)
N1 C15 C10 C11 -177.50(17)
C14 C15 C10 C9 -178.60(17)
N1 C15 C10 C9 3.4(2)
O1 C9 C10 C11 179.95(19)
C8 C9 C10 C11 0.3(3)
O1 C9 C10 C15 -1.0(3)
C8 C9 C10 C15 179.42(16)
C3 C4 C5 C6 0.4(3)
C1 C6 C5 C4 0.5(3)
C7 C6 C5 C4 -179.50(19)
C9 C8 C7 C6 -178.52(18)
C1 C6 C7 C8 -178.0(2)
C5 C6 C7 C8 1.9(3)
N1 C15 C14 C13 178.37(19)
C10 C15 C14 C13 0.4(3)
C21 C16 C17 C18 -0.6(3)
S1 C16 C17 C18 178.56(16)
C5 C6 C1 C2 -0.5(3)
C7 C6 C1 C2 179.5(2)
C5 C4 C3 C2 -1.3(3)
C5 C4 C3 F1 178.40(19)
C15 C10 C11 C12 -1.0(3)
C9 C10 C11 C12 178.14(19)
C18 C19 C20 C21 -0.1(3)
C16 C21 C20 C19 -0.1(3)
C10 C11 C12 C13 0.5(4)
C11 C12 C13 C14 0.5(4)
C15 C14 C13 C12 -0.9(3)
C20 C19 C18 C17 -0.1(4)
C16 C17 C18 C19 0.5(3)
F1 C3 C2 C1 -178.4(2)
C4 C3 C2 C1 1.3(4)
C6 C1 C2 C3 -0.4(3)
