# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc20qnq4
_database_code_depnum_ccdc_archive 'CCDC 1868826'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.molstruc.2019.126896 2019
loop_
_audit_author_name
_audit_author_address
'Jean Marcos Ferreira Custodio'
;UFG
Brazil
;
_audit_update_record             
;
2019-04-02 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Cl N O3 S'
_chemical_formula_weight         397.86

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   13.7952(7)
_cell_length_b                   7.5840(4)
_cell_length_c                   20.2728(9)
_cell_angle_alpha                90
_cell_angle_beta                 62.896(3)
_cell_angle_gamma                90
_cell_volume                     1888.07(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.37

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.736
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.336
_exptl_absorpt_coefficient_mu    0.334
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            27435
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.658
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3880
_reflns_number_gt                3394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.6910P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3880
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26675(3) 0.34683(5) 0.45487(2) 0.03990(13) Uani 1 1 d . . . . .
Cl1 Cl -0.28157(4) 0.56308(9) 0.35138(3) 0.07186(19) Uani 1 1 d . . . . .
C10 C 0.22638(12) 0.4687(2) 0.27831(9) 0.0380(3) Uani 1 1 d . . . . .
C6 C -0.10158(13) 0.4357(2) 0.23319(9) 0.0403(4) Uani 1 1 d . . . . .
N1 N 0.22457(12) 0.3757(2) 0.39301(8) 0.0474(4) Uani 1 1 d . . . . .
H1 H 0.1571(17) 0.369(3) 0.4085(11) 0.057 Uiso 1 1 d . U . . .
C16 C 0.29573(13) 0.5581(2) 0.47717(8) 0.0390(4) Uani 1 1 d . . . . .
O1 O 0.05143(10) 0.3919(2) 0.37336(8) 0.0622(4) Uani 1 1 d . . . . .
C15 C 0.28250(12) 0.4411(2) 0.32079(9) 0.0379(3) Uani 1 1 d . . . . .
O2 O 0.36587(10) 0.24945(17) 0.42373(7) 0.0561(3) Uani 1 1 d . . . . .
C9 C 0.10871(13) 0.4261(2) 0.30779(10) 0.0440(4) Uani 1 1 d . . . . .
O3 O 0.17427(10) 0.27745(18) 0.51741(7) 0.0561(3) Uani 1 1 d . . . . .
C11 C 0.28377(14) 0.5407(2) 0.20770(10) 0.0471(4) Uani 1 1 d . . . . .
H11 H 0.247139 0.562251 0.179722 0.057 Uiso 1 1 calc R U . . .
C8 C 0.06033(13) 0.4234(3) 0.25604(10) 0.0490(4) Uani 1 1 d . . . . .
H8 H 0.105819 0.411022 0.205555 0.059 Uiso 1 1 calc R U . . .
C1 C -0.20971(14) 0.4900(2) 0.26050(10) 0.0450(4) Uani 1 1 d . . . . .
C14 C 0.39379(13) 0.4776(3) 0.28944(10) 0.0488(4) Uani 1 1 d . . . . .
H14 H 0.432071 0.455284 0.316257 0.059 Uiso 1 1 calc R U . . .
C12 C 0.39268(15) 0.5810(3) 0.17800(10) 0.0527(5) Uani 1 1 d . . . . .
H12 H 0.4279(17) 0.631(3) 0.1281(12) 0.063 Uiso 1 1 d . U . . .
C5 C -0.05050(16) 0.3773(3) 0.15980(11) 0.0502(4) Uani 1 1 d . . . . .
H5 H 0.0233(18) 0.341(3) 0.1410(11) 0.060 Uiso 1 1 d . U . . .
C21 C 0.21072(17) 0.6741(3) 0.51389(10) 0.0520(4) Uani 1 1 d . . . . .
H21 H 0.1414(17) 0.637(3) 0.5246(12) 0.062 Uiso 1 1 d . U . . .
C13 C 0.44715(14) 0.5465(3) 0.21904(10) 0.0540(5) Uani 1 1 d . . . . .
H13 H 0.5215(18) 0.574(3) 0.1969(12) 0.065 Uiso 1 1 d . U . . .
C2 C -0.26340(16) 0.4876(3) 0.21747(12) 0.0593(5) Uani 1 1 d . . . . .
H2 H -0.335387 0.525035 0.237136 0.071 Uiso 1 1 calc R U . . .
C4 C -0.10370(18) 0.3748(3) 0.11660(12) 0.0620(5) Uani 1 1 d . . . . .
H4 H -0.067625 0.335819 0.067806 0.074 Uiso 1 1 calc R U . . .
C20 C 0.2352(2) 0.8410(3) 0.53133(13) 0.0751(7) Uani 1 1 d . . . . .
H20 H 0.179650 0.922169 0.555714 0.090 Uiso 1 1 calc R U . . .
C17 C 0.40158(16) 0.6040(3) 0.45906(11) 0.0594(5) Uani 1 1 d . . . . .
H17 H 0.458003 0.524473 0.434484 0.071 Uiso 1 1 calc R U . . .
C18 C 0.4229(2) 0.7689(4) 0.47773(14) 0.0827(8) Uani 1 1 d . . . . .
H18 H 0.493976 0.800228 0.466374 0.099 Uiso 1 1 calc R U . . .
C19 C 0.3409(3) 0.8857(3) 0.51260(15) 0.0845(8) Uani 1 1 d . . . . .
H19 H 0.356449 0.997593 0.523961 0.101 Uiso 1 1 calc R U . . .
C3 C -0.2103(2) 0.4299(3) 0.14550(13) 0.0676(6) Uani 1 1 d . . . . .
H3 H -0.246279 0.428048 0.116293 0.081 Uiso 1 1 calc R U . . .
C7 C -0.04540(13) 0.4382(2) 0.27942(10) 0.0439(4) Uani 1 1 d . . . . .
H7 H -0.088486 0.451380 0.330177 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S1 O2 1.4237(13) . ?
S1 O3 1.4276(12) . ?
S1 N1 1.6199(15) . ?
S1 C16 1.7597(17) . ?
Cl1 C1 1.7379(18) . ?
C10 C11 1.393(2) . ?
C10 C15 1.411(2) . ?
C10 C9 1.487(2) . ?
C6 C1 1.396(2) . ?
C6 C5 1.397(2) . ?
C6 C7 1.463(2) . ?
N1 C15 1.401(2) . ?
C16 C17 1.378(3) . ?
C16 C21 1.381(2) . ?
O1 C9 1.226(2) . ?
C15 C14 1.396(2) . ?
C9 C8 1.478(2) . ?
C11 C12 1.374(2) . ?
C8 C7 1.317(2) . ?
C1 C2 1.378(3) . ?
C14 C13 1.376(2) . ?
C12 C13 1.377(3) . ?
C5 C4 1.375(3) . ?
C21 C20 1.397(3) . ?
C2 C3 1.372(3) . ?
C4 C3 1.377(3) . ?
C20 C19 1.371(4) . ?
C17 C18 1.376(3) . ?
C18 C19 1.355(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
O2 S1 O3 119.45(8) . . ?
O2 S1 N1 109.75(8) . . ?
O3 S1 N1 104.27(8) . . ?
O2 S1 C16 107.55(8) . . ?
O3 S1 C16 108.85(8) . . ?
N1 S1 C16 106.24(8) . . ?
C11 C10 C15 118.16(14) . . ?
C11 C10 C9 120.21(15) . . ?
C15 C10 C9 121.62(14) . . ?
C1 C6 C5 116.45(16) . . ?
C1 C6 C7 121.62(16) . . ?
C5 C6 C7 121.93(15) . . ?
C15 N1 S1 128.46(12) . . ?
C17 C16 C21 121.27(18) . . ?
C17 C16 S1 119.92(15) . . ?
C21 C16 S1 118.81(14) . . ?
C14 C15 N1 122.10(15) . . ?
C14 C15 C10 119.21(15) . . ?
N1 C15 C10 118.68(14) . . ?
O1 C9 C8 119.38(15) . . ?
O1 C9 C10 121.88(15) . . ?
C8 C9 C10 118.74(15) . . ?
C12 C11 C10 122.23(16) . . ?
C7 C8 C9 121.84(17) . . ?
C2 C1 C6 122.04(17) . . ?
C2 C1 Cl1 117.63(14) . . ?
C6 C1 Cl1 120.32(13) . . ?
C13 C14 C15 120.34(16) . . ?
C11 C12 C13 118.79(17) . . ?
C4 C5 C6 121.74(18) . . ?
C16 C21 C20 118.0(2) . . ?
C12 C13 C14 121.17(16) . . ?
C3 C2 C1 119.79(19) . . ?
C5 C4 C3 120.08(19) . . ?
C19 C20 C21 120.2(2) . . ?
C18 C17 C16 119.3(2) . . ?
C19 C18 C17 120.3(2) . . ?
C18 C19 C20 120.9(2) . . ?
C2 C3 C4 119.91(18) . . ?
C8 C7 C6 126.25(17) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C15 -50.88(18) . . . . ?
O3 S1 N1 C15 -179.95(16) . . . . ?
C16 S1 N1 C15 65.13(18) . . . . ?
O2 S1 C16 C17 4.05(16) . . . . ?
O3 S1 C16 C17 134.82(15) . . . . ?
N1 S1 C16 C17 -113.43(15) . . . . ?
O2 S1 C16 C21 -174.87(13) . . . . ?
O3 S1 C16 C21 -44.10(15) . . . . ?
N1 S1 C16 C21 67.65(15) . . . . ?
S1 N1 C15 C14 6.0(3) . . . . ?
S1 N1 C15 C10 -174.84(13) . . . . ?
C11 C10 C15 C14 -3.4(2) . . . . ?
C9 C10 C15 C14 177.79(16) . . . . ?
C11 C10 C15 N1 177.37(16) . . . . ?
C9 C10 C15 N1 -1.4(2) . . . . ?
C11 C10 C9 O1 -167.15(18) . . . . ?
C15 C10 C9 O1 11.6(3) . . . . ?
C11 C10 C9 C8 13.5(2) . . . . ?
C15 C10 C9 C8 -167.71(16) . . . . ?
C15 C10 C11 C12 1.6(3) . . . . ?
C9 C10 C11 C12 -179.56(18) . . . . ?
O1 C9 C8 C7 20.8(3) . . . . ?
C10 C9 C8 C7 -159.90(18) . . . . ?
C5 C6 C1 C2 -0.5(3) . . . . ?
C7 C6 C1 C2 -179.80(17) . . . . ?
C5 C6 C1 Cl1 179.35(14) . . . . ?
C7 C6 C1 Cl1 0.0(2) . . . . ?
N1 C15 C14 C13 -178.16(18) . . . . ?
C10 C15 C14 C13 2.6(3) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C7 C6 C5 C4 179.84(18) . . . . ?
C17 C16 C21 C20 0.9(3) . . . . ?
S1 C16 C21 C20 179.82(14) . . . . ?
C11 C12 C13 C14 -1.9(3) . . . . ?
C15 C14 C13 C12 0.0(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
Cl1 C1 C2 C3 -179.58(17) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
C16 C21 C20 C19 -0.5(3) . . . . ?
C21 C16 C17 C18 -0.2(3) . . . . ?
S1 C16 C17 C18 -179.12(16) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C17 C18 C19 C20 1.4(4) . . . . ?
C21 C20 C19 C18 -0.7(4) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C9 C8 C7 C6 -179.47(16) . . . . ?
C1 C6 C7 C8 -165.82(18) . . . . ?
C5 C6 C7 C8 14.9(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
C5 H5 O3 0.95(2) 2.58(2) 3.342(2) 137.1(16) 4_565
C21 H21 O1 0.92(2) 2.53(2) 3.320(2) 144.1(17) 3_566
C12 H12 O2 0.98(2) 2.70(2) 3.274(2) 118.1(15) 2_655
C13 H13 O2 0.94(2) 2.59(2) 3.255(2) 128.5(16) 2_655

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichlorometane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc20qnr5
_database_code_depnum_ccdc_archive 'CCDC 1868827'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.molstruc.2019.126896 2019
loop_
_audit_author_name
_audit_author_address
'Jean Marcos Ferreira Custodio'
;UFG
Brazil
;
_audit_update_record             
;
2019-04-02 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 F N O3 S'
_chemical_formula_weight         381.41

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   26.984(3)
_cell_length_b                   7.6486(8)
_cell_length_c                   18.354(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.479(3)
_cell_angle_gamma                90
_cell_volume                     3613.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6524
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      26.32

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24691
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.582
_diffrn_reflns_theta_max         26.601
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3749
_reflns_number_gt                2712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+4.5555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3749
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33340(2) 0.49900(8) 0.19574(3) 0.04151(18) Uani 1 1 d . . . . .
C10 C 0.22063(8) 0.5226(3) 0.00162(12) 0.0349(5) Uani 1 1 d . . . . .
N1 N 0.27998(7) 0.4648(3) 0.12771(11) 0.0464(5) Uani 1 1 d . . . . .
H1 H 0.253675 0.433821 0.141955 0.056 Uiso 1 1 calc R U . . .
F1 F 0.00452(6) 0.6666(3) 0.06937(10) 0.0741(5) Uani 1 1 d . . . . .
O3 O 0.36490(7) 0.6205(2) 0.17008(10) 0.0524(5) Uani 1 1 d . . . . .
C16 C 0.36747(8) 0.2988(3) 0.21290(12) 0.0379(5) Uani 1 1 d . . . . .
C8 C 0.12878(9) 0.6338(3) -0.01389(14) 0.0435(6) Uani 1 1 d . . . . .
H8 H 0.1295(9) 0.678(3) -0.0624(15) 0.052 Uiso 1 1 d . U . . .
C15 C 0.27099(8) 0.4791(3) 0.04837(12) 0.0367(5) Uani 1 1 d . . . . .
O1 O 0.17989(7) 0.5020(3) 0.09903(11) 0.0661(6) Uani 1 1 d . . . . .
C6 C 0.03877(8) 0.7359(3) -0.03074(14) 0.0404(5) Uani 1 1 d . . . . .
C11 C 0.21277(9) 0.5380(3) -0.07692(13) 0.0447(6) Uani 1 1 d . . . . .
H11 H 0.179862 0.566712 -0.108624 0.054 Uiso 1 1 calc R U . . .
C14 C 0.31028(9) 0.4528(4) 0.01555(14) 0.0493(6) Uani 1 1 d . . . . .
H14 H 0.343427 0.423715 0.046301 0.059 Uiso 1 1 calc R U . . .
O2 O 0.31715(7) 0.5380(3) 0.26143(10) 0.0573(5) Uani 1 1 d . . . . .
C9 C 0.17673(9) 0.5491(3) 0.03359(14) 0.0413(6) Uani 1 1 d . . . . .
C7 C 0.08766(8) 0.6516(3) 0.01059(14) 0.0431(6) Uani 1 1 d . . . . .
H7 H 0.090146 0.606247 0.058567 0.052 Uiso 1 1 calc R U . . .
C17 C 0.40781(9) 0.2688(4) 0.18212(14) 0.0464(6) Uani 1 1 d . . . . .
H17 H 0.417093 0.353991 0.152498 0.056 Uiso 1 1 calc R U . . .
C21 C 0.35409(9) 0.1734(3) 0.25804(13) 0.0458(6) Uani 1 1 d . . . . .
H21 H 0.327256 0.193892 0.279020 0.055 Uiso 1 1 calc R U . . .
C5 C 0.02980(10) 0.8167(4) -0.10184(15) 0.0484(6) Uani 1 1 d . . . . .
H5 H 0.0573(10) 0.820(4) -0.1258(15) 0.058 Uiso 1 1 d . U . . .
C13 C 0.30086(9) 0.4692(4) -0.06249(15) 0.0534(7) Uani 1 1 d . . . . .
H13 H 0.327695 0.450963 -0.083710 0.064 Uiso 1 1 calc R U . . .
C2 C -0.04962(10) 0.8148(4) -0.03607(18) 0.0610(8) Uani 1 1 d . . . . .
H2 H -0.076190 0.812850 -0.013473 0.073 Uiso 1 1 calc R U . . .
C4 C -0.01701(10) 0.8947(4) -0.13866(16) 0.0602(7) Uani 1 1 d . . . . .
H4 H -0.021781 0.948888 -0.185635 0.072 Uiso 1 1 calc R U . . .
C12 C 0.25237(9) 0.5119(4) -0.10872(14) 0.0515(7) Uani 1 1 d . . . . .
H12 H 0.246200 0.523277 -0.161144 0.062 Uiso 1 1 calc R U . . .
C1 C -0.00254(10) 0.7404(4) -0.00046(16) 0.0488(6) Uani 1 1 d . . . . .
C18 C 0.43402(10) 0.1116(4) 0.19578(15) 0.0542(7) Uani 1 1 d . . . . .
H18 H 0.460756 0.089842 0.174720 0.065 Uiso 1 1 calc R U . . .
C19 C 0.42067(11) -0.0124(4) 0.24039(16) 0.0550(7) Uani 1 1 d . . . . .
H19 H 0.438570 -0.118002 0.249729 0.066 Uiso 1 1 calc R U . . .
C3 C -0.05688(11) 0.8927(5) -0.10591(19) 0.0656(9) Uani 1 1 d . . . . .
H3 H -0.0900(12) 0.941(4) -0.1312(18) 0.079 Uiso 1 1 d . U . . .
C20 C 0.38099(11) 0.0180(4) 0.27146(15) 0.0535(7) Uani 1 1 d . . . . .
H20 H 0.3722(11) -0.067(4) 0.2974(17) 0.064 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S1 O3 1.4309(18) . ?
S1 O2 1.4328(17) . ?
S1 N1 1.620(2) . ?
S1 C16 1.765(2) . ?
C10 C11 1.398(3) . ?
C10 C15 1.412(3) . ?
C10 C9 1.485(3) . ?
N1 C15 1.407(3) . ?
F1 C1 1.360(3) . ?
C16 C21 1.384(3) . ?
C16 C17 1.388(3) . ?
C8 C7 1.323(3) . ?
C8 C9 1.475(3) . ?
C15 C14 1.382(3) . ?
O1 C9 1.232(3) . ?
C6 C1 1.388(3) . ?
C6 C5 1.398(3) . ?
C6 C7 1.460(3) . ?
C11 C12 1.377(3) . ?
C14 C13 1.383(3) . ?
C17 C18 1.379(4) . ?
C21 C20 1.375(4) . ?
C5 C4 1.377(4) . ?
C13 C12 1.368(3) . ?
C2 C1 1.366(4) . ?
C2 C3 1.373(4) . ?
C4 C3 1.381(4) . ?
C18 C19 1.370(4) . ?
C19 C20 1.376(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
O3 S1 O2 120.26(12) . . ?
O3 S1 N1 109.28(11) . . ?
O2 S1 N1 104.82(11) . . ?
O3 S1 C16 107.04(10) . . ?
O2 S1 C16 107.78(11) . . ?
N1 S1 C16 107.01(11) . . ?
C11 C10 C15 117.8(2) . . ?
C11 C10 C9 120.3(2) . . ?
C15 C10 C9 121.9(2) . . ?
C15 N1 S1 128.47(16) . . ?
C21 C16 C17 120.4(2) . . ?
C21 C16 S1 119.52(18) . . ?
C17 C16 S1 120.08(18) . . ?
C7 C8 C9 121.4(2) . . ?
C14 C15 N1 121.6(2) . . ?
C14 C15 C10 119.6(2) . . ?
N1 C15 C10 118.85(19) . . ?
C1 C6 C5 115.4(2) . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C7 123.8(2) . . ?
C12 C11 C10 121.9(2) . . ?
C15 C14 C13 120.8(2) . . ?
O1 C9 C8 119.7(2) . . ?
O1 C9 C10 121.0(2) . . ?
C8 C9 C10 119.2(2) . . ?
C8 C7 C6 126.0(2) . . ?
C18 C17 C16 119.5(2) . . ?
C20 C21 C16 119.2(2) . . ?
C4 C5 C6 121.7(2) . . ?
C12 C13 C14 120.5(2) . . ?
C1 C2 C3 118.6(3) . . ?
C5 C4 C3 120.1(3) . . ?
C13 C12 C11 119.4(2) . . ?
F1 C1 C2 118.1(2) . . ?
F1 C1 C6 117.7(2) . . ?
C2 C1 C6 124.2(3) . . ?
C19 C18 C17 120.0(2) . . ?
C18 C19 C20 120.5(3) . . ?
C2 C3 C4 120.0(3) . . ?
C21 C20 C19 120.4(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
C3 H3 O2 0.95(3) 2.69(3) 3.577(3) 156(3) 8_465
C5 H5 O3 0.97(3) 2.51(3) 3.466(3) 169(2) 7_565
C8 H8 O3 0.96(3) 2.55(3) 3.475(3) 163(2) 7_565
C20 H20 O1 0.88(3) 2.73(3) 3.273(3) 121(2) 4_545

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.047

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_g22_0m
_database_code_depnum_ccdc_archive 'CCDC 1904244'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'Sulfonamide chalcone'
_chemical_name_systematic        
(E)-3-(2-chlorophenyl)-1-(2-(phenylsulfonylamine)phenyl)prop-2-en-1-one
_chemical_formula_moiety         'C22 H19 N O4 S'
_chemical_formula_sum            'C22 H19 N O4 S'
_chemical_formula_weight         393.44
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   11.6707(12)
_cell_length_b                   12.5558(13)
_cell_length_c                   13.3311(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.004(3)
_cell_angle_gamma                90
_cell_volume                     1917.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1418 before and 0.0524 after correction. The Ratio of minimum to maximum transmission is 0.8137. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.254
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.532
_diffrn_reflns_theta_min         2.127
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3122
_reflns_number_total             3952
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.119
_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)+(0.0551P)²+1.1934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1389
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C16(H16), C2(H2), C22(H22), C18(H18), C13(H13), C5(H5),
 C21(H21), C4(H4), C3(H3), C20(H20), C19(H19), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.093
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18240(5) 0.28506(5) 0.20173(5) 0.04068(18) Uani 1 1 d . . . . .
O1 O 0.37135(14) 0.50200(13) 0.11857(14) 0.0517(5) Uani 1 1 d . . . . .
O4 O 0.80349(15) 0.58507(13) 0.11639(15) 0.0523(5) Uani 1 1 d . . . . .
O3 O 0.15797(16) 0.17415(15) 0.19175(14) 0.0572(5) Uani 1 1 d . . . . .
O2 O 0.08812(14) 0.35940(16) 0.18367(14) 0.0571(5) Uani 1 1 d . . . . .
N1 N 0.26591(15) 0.32091(16) 0.12195(14) 0.0391(4) Uani 1 1 d . . . . .
H1 H 0.2462 0.3944 0.1137 0.047 Uiso 1 1 d R . . . .
C11 C 0.47102(18) 0.33836(17) 0.11025(16) 0.0349(5) Uani 1 1 d . . . . .
C17 C 0.26449(18) 0.30823(18) 0.32574(17) 0.0367(5) Uani 1 1 d . . . . .
C12 C 0.37412(18) 0.27308(17) 0.11573(16) 0.0356(5) Uani 1 1 d . . . . .
C10 C 0.46585(19) 0.45639(18) 0.11865(16) 0.0374(5) Uani 1 1 d . . . . .
C9 C 0.5729(2) 0.52042(18) 0.12760(17) 0.0397(5) Uani 1 1 d . . . . .
H9 H 0.6420 0.4881 0.1186 0.048 Uiso 1 1 calc R . . . .
C1 C 0.7762(2) 0.68698(18) 0.13505(16) 0.0378(5) Uani 1 1 d . . . . .
C6 C 0.6625(2) 0.70483(18) 0.15443(17) 0.0385(5) Uani 1 1 d . . . . .
C8 C 0.5719(2) 0.62418(19) 0.14840(17) 0.0412(5) Uani 1 1 d . . . . .
H8 H 0.5012 0.6494 0.1613 0.049 Uiso 1 1 calc R . . . .
C16 C 0.5734(2) 0.28720(19) 0.0952(2) 0.0468(6) Uani 1 1 d . . . . .
H16 H 0.6381 0.3284 0.0895 0.056 Uiso 1 1 calc R . . . .
C2 C 0.8522(2) 0.7718(2) 0.13470(18) 0.0468(6) Uani 1 1 d . . . . .
H2 H 0.9258 0.7600 0.1198 0.056 Uiso 1 1 calc R . . . .
C22 C 0.2909(2) 0.2263(2) 0.3946(2) 0.0482(6) Uani 1 1 d . . . . .
H22 H 0.2671 0.1570 0.3768 0.058 Uiso 1 1 calc R . . . .
C18 C 0.3003(2) 0.4113(2) 0.3516(2) 0.0499(6) Uani 1 1 d . . . . .
H18 H 0.2824 0.4661 0.3042 0.060 Uiso 1 1 calc R . . . .
C13 C 0.3831(2) 0.1633(2) 0.1091(2) 0.0489(6) Uani 1 1 d . . . . .
H13 H 0.3187 0.1207 0.1127 0.059 Uiso 1 1 calc R . . . .
C5 C 0.6343(2) 0.8090(2) 0.1769(2) 0.0488(6) Uani 1 1 d . . . . .
H5 H 0.5607 0.8227 0.1910 0.059 Uiso 1 1 calc R . . . .
C21 C 0.3541(2) 0.2493(3) 0.4916(2) 0.0597(7) Uani 1 1 d . . . . .
H21 H 0.3722 0.1949 0.5394 0.072 Uiso 1 1 calc R . . . .
C4 C 0.7113(3) 0.8923(2) 0.1790(2) 0.0549(7) Uani 1 1 d . . . . .
H4 H 0.6904 0.9606 0.1956 0.066 Uiso 1 1 calc R . . . .
C3 C 0.8196(2) 0.8731(2) 0.15622(19) 0.0517(6) Uani 1 1 d . . . . .
H3 H 0.8713 0.9293 0.1554 0.062 Uiso 1 1 calc R . . . .
C20 C 0.3898(2) 0.3512(3) 0.5173(2) 0.0603(7) Uani 1 1 d . . . . .
H20 H 0.4327 0.3655 0.5821 0.072 Uiso 1 1 calc R . . . .
C19 C 0.3625(3) 0.4321(2) 0.4480(2) 0.0602(7) Uani 1 1 d . . . . .
H19 H 0.3862 0.5014 0.4661 0.072 Uiso 1 1 calc R . . . .
C15 C 0.5812(2) 0.1789(2) 0.0886(2) 0.0575(7) Uani 1 1 d . . . . .
H15 H 0.6501 0.1472 0.0782 0.069 Uiso 1 1 calc R . . . .
C14 C 0.4861(3) 0.1170(2) 0.0974(2) 0.0582(7) Uani 1 1 d . . . . .
H14 H 0.4918 0.0432 0.0953 0.070 Uiso 1 1 calc R . . . .
C7 C 0.9185(2) 0.5633(2) 0.0999(3) 0.0685(8) Uani 1 1 d . . . . .
H7A H 0.9310 0.6001 0.0398 0.103 Uiso 1 1 calc GR . . . .
H7B H 0.9273 0.4881 0.0910 0.103 Uiso 1 1 calc GR . . . .
H7C H 0.9746 0.5871 0.1579 0.103 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1 O3 1.4225(19) . ?
S1 O2 1.4279(18) . ?
S1 N1 1.6369(18) . ?
S1 C17 1.769(2) . ?
O1 C10 1.243(3) . ?
O4 C1 1.353(3) . ?
O4 C7 1.427(3) . ?
N1 C12 1.415(3) . ?
C11 C12 1.410(3) . ?
C11 C10 1.488(3) . ?
C11 C16 1.405(3) . ?
C17 C22 1.374(3) . ?
C17 C18 1.384(3) . ?
C12 C13 1.387(3) . ?
C10 C9 1.471(3) . ?
C9 C8 1.333(3) . ?
C1 C6 1.418(3) . ?
C1 C2 1.386(3) . ?
C6 C8 1.454(3) . ?
C6 C5 1.395(3) . ?
C16 C15 1.367(4) . ?
C2 C3 1.374(4) . ?
C22 C21 1.390(4) . ?
C18 C19 1.375(4) . ?
C13 C14 1.371(4) . ?
C5 C4 1.375(4) . ?
C21 C20 1.369(4) . ?
C4 C3 1.377(4) . ?
C20 C19 1.370(4) . ?
C15 C14 1.379(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
O3 S1 O2 119.33(11) . . ?
O3 S1 N1 110.00(11) . . ?
O3 S1 C17 108.15(11) . . ?
O2 S1 N1 104.23(10) . . ?
O2 S1 C17 108.20(11) . . ?
N1 S1 C17 106.17(10) . . ?
C1 O4 C7 118.1(2) . . ?
C12 N1 S1 124.76(15) . . ?
C12 C11 C10 122.04(19) . . ?
C16 C11 C12 117.0(2) . . ?
C16 C11 C10 120.9(2) . . ?
C22 C17 S1 120.92(19) . . ?
C22 C17 C18 121.0(2) . . ?
C18 C17 S1 118.06(18) . . ?
C11 C12 N1 119.35(19) . . ?
C13 C12 N1 120.3(2) . . ?
C13 C12 C11 120.3(2) . . ?
O1 C10 C11 120.5(2) . . ?
O1 C10 C9 119.2(2) . . ?
C9 C10 C11 120.28(19) . . ?
C8 C9 C10 120.7(2) . . ?
O4 C1 C6 116.38(19) . . ?
O4 C1 C2 123.5(2) . . ?
C2 C1 C6 120.1(2) . . ?
C1 C6 C8 125.1(2) . . ?
C5 C6 C1 117.0(2) . . ?
C5 C6 C8 117.8(2) . . ?
C9 C8 C6 131.1(2) . . ?
C15 C16 C11 122.2(2) . . ?
C3 C2 C1 120.5(2) . . ?
C17 C22 C21 118.5(2) . . ?
C19 C18 C17 119.4(2) . . ?
C14 C13 C12 120.5(2) . . ?
C4 C5 C6 122.5(2) . . ?
C20 C21 C22 120.6(3) . . ?
C5 C4 C3 119.1(2) . . ?
C2 C3 C4 120.7(2) . . ?
C21 C20 C19 120.3(3) . . ?
C20 C19 C18 120.2(3) . . ?
C16 C15 C14 119.4(2) . . ?
C13 C14 C15 120.6(2) . . ?

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
N1 H1 O1 0.95 1.98 2.590(2) 119.7 .
C22 H22 O1 0.93 2.54 3.380(3) 150.6 2_545
C18 H18 O3 0.93 2.70 3.401(3) 132.7 2
C5 H5 O2 0.93 2.67 3.526(3) 153.5 2
C7 H7B O2 0.96 2.60 3.298(4) 129.5 1_655

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc20qns6
_database_code_depnum_ccdc_archive 'CCDC 1868828'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.molstruc.2019.126896 2019
loop_
_audit_author_name
_audit_author_address
'Jean Marcos Ferreira Custodio'
;UFG
Brazil
;
_audit_update_record             
;
2019-04-02 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 F N O3 S'
_chemical_formula_weight         381.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   13.1059(5)
_cell_length_b                   17.5044(8)
_cell_length_c                   8.1948(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.278(2)
_cell_angle_gamma                90
_cell_volume                     1836.98(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8438
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.02

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.213
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_max          0.647
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7002
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23587
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.590
_diffrn_reflns_theta_max         26.418
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3762
_reflns_number_gt                2982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.5715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0285(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
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_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
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_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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

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

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.046

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_g32_1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc21xj8s
_database_code_depnum_ccdc_archive 'CCDC 1904245'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1007/s00044-019-02384-8 2019
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_vrf_mo_g32_1_0m                 
;
RESPONSE: The atom O4 does not vibrate along S1-O4 bond.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'Sulfonamide chalcone'
_chemical_name_systematic        
(E)-3-(2-methoxyphenyl)-1-(2-(phenylsulfonylamine)phenyl)prop-2-en-1-one
_chemical_formula_moiety         'C21 H16 N2 O5 S'
_chemical_formula_sum            'C21 H16 N2 O5 S'
_chemical_formula_weight         408.42
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   14.0149(16)
_cell_length_b                   7.6562(9)
_cell_length_c                   18.380(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.242(4)
_cell_angle_gamma                90
_cell_volume                     1934.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1361 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.8599. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.095
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30977
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.829
_diffrn_reflns_theta_min         1.481
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2976
_reflns_number_total             3950
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.050
_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)+(0.0502P)²+0.7905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C21 \\sim C20 \\sim C19 \\sim C18 \\sim C17: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
O4 \\sim S1 \\sim O5: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C7(H7), C8(H8), C14(H14), C13(H13), C12(H12), C4(H4),
 C17(H17), C21(H21), C18(H18), C20(H20), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31610(3) 0.19620(9) 0.14857(2) 0.05280(19) Uani 1 1 d . U . . .
O1 O 0.50851(10) 0.2684(3) 0.33653(8) 0.0774(6) Uani 1 1 d . . . . .
O2 O 0.97082(12) 0.5115(3) 0.68939(11) 0.1051(8) Uani 1 1 d . . . . .
O5 O 0.39704(10) 0.2487(3) 0.11688(8) 0.0789(6) Uani 1 1 d . U . . .
O3 O 0.94477(11) 0.5197(3) 0.57105(11) 0.0845(6) Uani 1 1 d . . . . .
N2 N 0.35547(11) 0.2128(3) 0.23723(8) 0.0599(5) Uani 1 1 d . . . . .
H2 H 0.4132 0.2546 0.2506 0.072 Uiso 1 1 calc R . . . .
N1 N 0.91853(12) 0.4908(3) 0.62902(11) 0.0627(5) Uani 1 1 d . . . . .
C2 C 0.81829(13) 0.4271(3) 0.62611(11) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.75894(13) 0.4051(3) 0.55750(10) 0.0442(5) Uani 1 1 d . . . . .
H1 H 0.7817 0.4315 0.5145 0.053 Uiso 1 1 calc R . . . .
C6 C 0.66458(13) 0.3431(3) 0.55325(10) 0.0417(4) Uani 1 1 d . . . . .
C7 C 0.60336(13) 0.3163(3) 0.47994(10) 0.0466(5) Uani 1 1 d . . . . .
H7 H 0.6312 0.3455 0.4396 0.056 Uiso 1 1 calc R . . . .
C8 C 0.51384(13) 0.2560(3) 0.46413(10) 0.0486(5) Uani 1 1 d . . . . .
H8 H 0.4824 0.2244 0.5023 0.058 Uiso 1 1 calc R . . . .
C9 C 0.46300(13) 0.2381(3) 0.38617(10) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.35922(12) 0.1836(3) 0.36874(9) 0.0396(4) Uani 1 1 d . . . . .
C15 C 0.30787(12) 0.1680(3) 0.29507(9) 0.0425(5) Uani 1 1 d . . . . .
C14 C 0.21151(13) 0.1114(3) 0.28101(10) 0.0517(5) Uani 1 1 d . . . . .
H14 H 0.1781 0.0990 0.2323 0.062 Uiso 1 1 calc R . . . .
C13 C 0.16546(14) 0.0738(3) 0.33904(11) 0.0548(6) Uani 1 1 d . . . . .
H13 H 0.1009 0.0373 0.3291 0.066 Uiso 1 1 calc R . . . .
C12 C 0.21385(14) 0.0898(3) 0.41136(11) 0.0557(6) Uani 1 1 d . . . . .
H12 H 0.1823 0.0647 0.4502 0.067 Uiso 1 1 calc R . . . .
C11 C 0.30950(14) 0.1431(3) 0.42577(10) 0.0485(5) Uani 1 1 d . . . . .
H11 H 0.3422(15) 0.152(3) 0.4767(12) 0.058 Uiso 1 1 d R . . . .
C5 C 0.63325(15) 0.3062(3) 0.61916(11) 0.0525(5) Uani 1 1 d . . . . .
H5 H 0.5700(17) 0.262(3) 0.6183(12) 0.063 Uiso 1 1 d R . . . .
C4 C 0.69435(16) 0.3296(4) 0.68682(12) 0.0673(7) Uani 1 1 d . . . . .
H4 H 0.6723 0.3039 0.7302 0.081 Uiso 1 1 calc R . . . .
C3 C 0.78816(16) 0.3908(4) 0.69106(12) 0.0622(6) Uani 1 1 d . . . . .
H3 H 0.8343(17) 0.408(3) 0.7384(13) 0.075 Uiso 1 1 d R . . . .
C16 C 0.22328(14) 0.3525(3) 0.12498(9) 0.0467(5) Uani 1 1 d . U . . .
C17 C 0.12758(14) 0.2970(3) 0.10536(12) 0.0556(6) Uani 1 1 d . U . . .
H17 H 0.1131 0.1784 0.1039 0.067 Uiso 1 1 calc R . . . .
C21 C 0.2454(2) 0.5280(4) 0.12535(11) 0.0686(7) Uani 1 1 d . U . . .
H21 H 0.3096 0.5657 0.1372 0.082 Uiso 1 1 calc R . . . .
C18 C 0.05424(18) 0.4178(4) 0.08802(14) 0.0760(8) Uani 1 1 d . U . . .
H18 H -0.0100 0.3808 0.0750 0.091 Uiso 1 1 calc R . . . .
C20 C 0.1693(3) 0.6478(4) 0.10747(14) 0.0850(9) Uani 1 1 d . U . . .
H20 H 0.1825 0.7669 0.1075 0.102 Uiso 1 1 calc R . . . .
C19 C 0.0752(2) 0.5898(5) 0.08989(16) 0.0860(9) Uani 1 1 d . U . . .
H19 H 0.0248 0.6705 0.0791 0.103 Uiso 1 1 calc R . . . .
O4 O 0.27246(11) 0.0286(2) 0.13122(8) 0.0662(4) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1 O5 1.4300(15) . ?
S1 N2 1.6205(16) . ?
S1 C16 1.759(2) . ?
S1 O4 1.4303(18) . ?
O1 C9 1.233(2) . ?
O2 N1 1.215(2) . ?
O3 N1 1.213(2) . ?
N2 C15 1.403(2) . ?
N1 C2 1.478(2) . ?
C2 C1 1.379(2) . ?
C2 C3 1.370(3) . ?
C1 C6 1.393(2) . ?
C6 C7 1.464(2) . ?
C6 C5 1.395(3) . ?
C7 C8 1.315(3) . ?
C8 C9 1.477(3) . ?
C9 C10 1.487(2) . ?
C10 C15 1.409(2) . ?
C10 C11 1.402(2) . ?
C15 C14 1.393(2) . ?
C14 C13 1.380(3) . ?
C13 C12 1.375(3) . ?
C12 C11 1.377(3) . ?
C5 C4 1.377(3) . ?
C4 C3 1.384(3) . ?
C16 C17 1.386(3) . ?
C16 C21 1.378(3) . ?
C17 C18 1.373(3) . ?
C21 C20 1.397(4) . ?
C18 C19 1.348(4) . ?
C20 C19 1.369(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
O5 S1 N2 104.24(8) . . ?
O5 S1 C16 108.40(11) . . ?
O5 S1 O4 120.00(11) . . ?
N2 S1 C16 106.56(9) . . ?
O4 S1 N2 109.97(10) . . ?
O4 S1 C16 106.97(10) . . ?
C15 N2 S1 128.59(13) . . ?
O2 N1 C2 118.4(2) . . ?
O3 N1 O2 123.09(19) . . ?
O3 N1 C2 118.49(18) . . ?
C1 C2 N1 118.23(18) . . ?
C3 C2 N1 119.18(18) . . ?
C3 C2 C1 122.58(18) . . ?
C2 C1 C6 119.33(17) . . ?
C1 C6 C7 118.62(16) . . ?
C1 C6 C5 118.44(17) . . ?
C5 C6 C7 122.92(17) . . ?
C8 C7 C6 127.97(18) . . ?
C7 C8 C9 120.39(17) . . ?
O1 C9 C8 118.64(17) . . ?
O1 C9 C10 121.25(16) . . ?
C8 C9 C10 120.11(16) . . ?
C15 C10 C9 121.72(15) . . ?
C11 C10 C9 120.59(16) . . ?
C11 C10 C15 117.69(16) . . ?
N2 C15 C10 118.56(15) . . ?
C14 C15 N2 121.47(16) . . ?
C14 C15 C10 119.96(16) . . ?
C13 C14 C15 120.24(17) . . ?
C12 C13 C14 120.79(17) . . ?
C13 C12 C11 119.37(17) . . ?
C12 C11 C10 121.94(18) . . ?
C4 C5 C6 120.81(19) . . ?
C5 C4 C3 120.8(2) . . ?
C2 C3 C4 118.07(19) . . ?
C17 C16 S1 119.16(18) . . ?
C21 C16 S1 120.47(18) . . ?
C21 C16 C17 120.4(2) . . ?
C18 C17 C16 119.8(2) . . ?
C16 C21 C20 118.6(2) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C20 C21 119.9(3) . . ?
C18 C19 C20 121.2(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
N2 H2 O1 0.86 1.86 2.566(2) 138.0 .
C8 H8 O5 0.93 2.63 3.515(2) 160.3 4_566
C11 H11 O5 0.96(2) 2.65(2) 3.585(2) 163.6(17) 4_566
C5 H5 O5 0.95(2) 2.42(2) 3.329(2) 160.9(19) 4_566
C20 H20 O4 0.93 2.36 3.246(4) 158.5 1_565
C19 H19 O3 0.93 2.62 3.486(4) 156.0 4_475

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N2 C15 C10 175.95(17) . . . . ?
S1 N2 C15 C14 -5.0(3) . . . . ?
S1 C16 C17 C18 178.91(17) . . . . ?
S1 C16 C21 C20 -178.93(16) . . . . ?
O1 C9 C10 C15 -1.5(3) . . . . ?
O1 C9 C10 C11 177.5(2) . . . . ?
O2 N1 C2 C1 179.5(2) . . . . ?
O2 N1 C2 C3 -1.1(3) . . . . ?
O5 S1 N2 C15 -176.0(2) . . . . ?
O5 S1 C16 C17 139.54(16) . . . . ?
O5 S1 C16 C21 -39.87(18) . . . . ?
O3 N1 C2 C1 -0.6(3) . . . . ?
O3 N1 C2 C3 178.8(2) . . . . ?
N2 S1 C16 C17 -108.78(16) . . . . ?
N2 S1 C16 C21 71.81(17) . . . . ?
N2 C15 C14 C13 -177.8(2) . . . . ?
N1 C2 C1 C6 179.15(19) . . . . ?
N1 C2 C3 C4 -179.3(2) . . . . ?
C2 C1 C6 C7 -178.47(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C6 C7 C8 178.5(2) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C6 C7 C8 C9 179.9(2) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C7 C6 C5 C4 178.4(2) . . . . ?
C7 C8 C9 O1 5.3(3) . . . . ?
C7 C8 C9 C10 -175.1(2) . . . . ?
C8 C9 C10 C15 178.9(2) . . . . ?
C8 C9 C10 C11 -2.1(3) . . . . ?
C9 C10 C15 N2 -2.8(3) . . . . ?
C9 C10 C15 C14 178.1(2) . . . . ?
C9 C10 C11 C12 -179.1(2) . . . . ?
C10 C15 C14 C13 1.3(3) . . . . ?
C15 C10 C11 C12 0.0(3) . . . . ?
C15 C14 C13 C12 -0.6(4) . . . . ?
C14 C13 C12 C11 -0.3(4) . . . . ?
C13 C12 C11 C10 0.6(4) . . . . ?
C11 C10 C15 N2 178.16(19) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C3 C2 C1 C6 -0.2(3) . . . . ?
C16 S1 N2 C15 69.5(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C16 C21 C20 C19 -0.2(4) . . . . ?
C17 C16 C21 C20 1.7(3) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C21 C16 C17 C18 -1.7(3) . . . . ?
C21 C20 C19 C18 -1.3(4) . . . . ?
O4 S1 N2 C15 -46.1(2) . . . . ?
O4 S1 C16 C17 8.82(17) . . . . ?
O4 S1 C16 C21 -170.60(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_g27_0m
_database_code_depnum_ccdc_archive 'CCDC 1949070'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2019-08-24 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Cl N O3 S'
_chemical_formula_sum            'C21 H16 Cl N O3 S'
_chemical_formula_weight         397.86
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4130(4)
_cell_length_b                   9.8066(5)
_cell_length_c                   13.1211(7)
_cell_angle_alpha                73.231(2)
_cell_angle_beta                 85.049(2)
_cell_angle_gamma                69.892(2)
_cell_volume                     973.22(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1499 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.8342.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.401
_exptl_crystal_size_min          0.283
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37156
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         1.621
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2917
_reflns_number_total             4007
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.022
_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)+(0.0470P)²+0.3270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C2(H2), C4(H4), C11(H11), C9(H9), C3(H3), C15(H15), C21(H21),
 C12(H12), C14(H14), C20(H20), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.058
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50039(6) 0.30188(7) 0.81956(4) 0.0660(2) Uani 1 1 d . . . . .
Cl1 Cl 1.82444(11) 0.12271(12) 0.29998(9) 0.1336(4) Uani 1 1 d . . . . .
C1 C 0.7363(2) 0.4403(2) 0.77496(15) 0.0543(5) Uani 1 1 d . . . . .
O1 O 0.8254(2) 0.3237(2) 0.59161(13) 0.0875(6) Uani 1 1 d . . . . .
C10 C 1.3163(3) 0.2264(2) 0.45813(15) 0.0574(5) Uani 1 1 d . . . . .
O3 O 0.40215(19) 0.3898(2) 0.88708(14) 0.0841(5) Uani 1 1 d . . . . .
C6 C 0.8905(2) 0.4259(2) 0.71966(15) 0.0519(5) Uani 1 1 d . . . . .
C16 C 0.6453(2) 0.1374(2) 0.89964(16) 0.0546(5) Uani 1 1 d . . . . .
C8 C 1.1043(3) 0.3216(3) 0.58714(16) 0.0622(5) Uani 1 1 d . . . . .
H8 H 1.183983 0.345506 0.617054 0.075 Uiso 1 1 calc R . . . .
C7 C 0.9321(3) 0.3552(3) 0.63013(16) 0.0601(5) Uani 1 1 d . . . . .
N1 N 0.6140(2) 0.3931(2) 0.74106(15) 0.0659(5) Uani 1 1 d . . . . .
C5 C 1.0039(3) 0.4815(2) 0.75233(17) 0.0591(5) Uani 1 1 d . . . . .
H5 H 1.104973 0.475845 0.716074 0.071 Uiso 1 1 calc R . . . .
O2 O 0.4177(2) 0.2592(2) 0.74903(13) 0.0933(6) Uani 1 1 d . . . . .
C2 C 0.7051(3) 0.5035(3) 0.85954(18) 0.0664(6) Uani 1 1 d . . . . .
H2 H 0.603992 0.511726 0.896146 0.080 Uiso 1 1 calc R . . . .
C4 C 0.9712(3) 0.5439(3) 0.83582(19) 0.0672(6) Uani 1 1 d . . . . .
H4 H 1.049354 0.579327 0.856090 0.081 Uiso 1 1 calc R . . . .
C11 C 1.4423(3) 0.2740(3) 0.48221(18) 0.0703(6) Uani 1 1 d . . . . .
H11 H 1.421599 0.327905 0.532581 0.084 Uiso 1 1 calc R . . . .
C9 C 1.1506(3) 0.2590(2) 0.50795(16) 0.0614(5) Uani 1 1 d . . . . .
H9 H 1.069486 0.233131 0.481217 0.074 Uiso 1 1 calc R . . . .
C3 C 0.8213(3) 0.5539(3) 0.88975(19) 0.0708(6) Uani 1 1 d . . . . .
H3 H 0.799051 0.595170 0.947101 0.085 Uiso 1 1 calc R . . . .
C15 C 1.3517(3) 0.1460(3) 0.38271(18) 0.0715(6) Uani 1 1 d . . . . .
H15 H 1.269505 0.112988 0.364793 0.086 Uiso 1 1 calc R . . . .
C21 C 0.6455(3) 0.1090(3) 1.00815(18) 0.0710(6) Uani 1 1 d . . . . .
H21 H 0.570994 0.178302 1.040615 0.085 Uiso 1 1 calc R . . . .
C13 C 1.6274(3) 0.1633(3) 0.3600(2) 0.0774(7) Uani 1 1 d . . . . .
C12 C 1.5969(3) 0.2435(3) 0.4335(2) 0.0754(6) Uani 1 1 d . . . . .
H12 H 1.679568 0.276995 0.450240 0.091 Uiso 1 1 calc R . . . .
C14 C 1.5069(4) 0.1144(3) 0.3339(2) 0.0849(7) Uani 1 1 d . . . . .
H14 H 1.529254 0.060205 0.283650 0.102 Uiso 1 1 calc R . . . .
C20 C 0.7580(4) -0.0243(3) 1.0690(2) 0.0907(8) Uani 1 1 d . . . . .
H20 H 0.756828 -0.045610 1.142791 0.109 Uiso 1 1 calc R . . . .
C17 C 0.7590(4) 0.0352(3) 0.8525(2) 0.0851(8) Uani 1 1 d . . . . .
H17 H 0.760231 0.054031 0.778884 0.102 Uiso 1 1 calc R . . . .
C18 C 0.8709(4) -0.0953(3) 0.9154(3) 0.1064(10) Uani 1 1 d . . . . .
H18 H 0.948255 -0.164456 0.883983 0.128 Uiso 1 1 calc R . . . .
C19 C 0.8688(4) -0.1230(3) 1.0224(3) 0.0988(9) Uani 1 1 d . . . . .
H19 H 0.944793 -0.211254 1.064171 0.119 Uiso 1 1 calc R . . . .
H1 H 0.645(3) 0.359(3) 0.6896(19) 0.070(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1 O3 1.4265(17) . ?
S1 C16 1.756(2) . ?
S1 N1 1.6314(19) . ?
S1 O2 1.4320(17) . ?
Cl1 C13 1.741(2) . ?
C1 C6 1.414(3) . ?
C1 N1 1.413(3) . ?
C1 C2 1.385(3) . ?
O1 C7 1.231(2) . ?
C10 C11 1.387(3) . ?
C10 C9 1.460(3) . ?
C10 C15 1.388(3) . ?
C6 C7 1.489(3) . ?
C6 C5 1.398(3) . ?
C16 C21 1.370(3) . ?
C16 C17 1.378(3) . ?
C8 C7 1.471(3) . ?
C8 C9 1.320(3) . ?
C5 C4 1.367(3) . ?
C2 C3 1.367(3) . ?
C4 C3 1.379(3) . ?
C11 C12 1.374(3) . ?
C15 C14 1.379(3) . ?
C21 C20 1.385(4) . ?
C13 C12 1.368(3) . ?
C13 C14 1.365(4) . ?
C20 C19 1.342(4) . ?
C17 C18 1.378(4) . ?
C18 C19 1.351(5) . ?

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
O3 S1 C16 108.15(10) . . ?
O3 S1 N1 109.68(12) . . ?
O3 S1 O2 119.86(11) . . ?
N1 S1 C16 105.92(9) . . ?
O2 S1 C16 108.36(11) . . ?
O2 S1 N1 104.04(10) . . ?
N1 C1 C6 119.15(19) . . ?
C2 C1 C6 119.98(19) . . ?
C2 C1 N1 120.85(19) . . ?
C11 C10 C9 122.56(19) . . ?
C11 C10 C15 117.6(2) . . ?
C15 C10 C9 119.8(2) . . ?
C1 C6 C7 122.07(18) . . ?
C5 C6 C1 117.19(18) . . ?
C5 C6 C7 120.75(18) . . ?
C21 C16 S1 120.83(17) . . ?
C21 C16 C17 119.7(2) . . ?
C17 C16 S1 119.43(18) . . ?
C9 C8 C7 122.8(2) . . ?
O1 C7 C6 121.31(19) . . ?
O1 C7 C8 119.3(2) . . ?
C8 C7 C6 119.34(18) . . ?
C1 N1 S1 125.26(15) . . ?
C4 C5 C6 122.1(2) . . ?
C3 C2 C1 120.7(2) . . ?
C5 C4 C3 119.5(2) . . ?
C12 C11 C10 121.6(2) . . ?
C8 C9 C10 126.5(2) . . ?
C2 C3 C4 120.5(2) . . ?
C14 C15 C10 121.1(2) . . ?
C16 C21 C20 119.2(2) . . ?
C12 C13 Cl1 118.8(2) . . ?
C14 C13 Cl1 120.0(2) . . ?
C14 C13 C12 121.2(2) . . ?
C13 C12 C11 119.0(2) . . ?
C13 C14 C15 119.5(2) . . ?
C19 C20 C21 120.6(3) . . ?
C16 C17 C18 119.5(3) . . ?
C19 C18 C17 120.3(3) . . ?
C20 C19 C18 120.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_g33_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1949072'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2019-08-24 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H16 Br N O3 S)'
_chemical_formula_sum            'C42 H32 Br2 N2 O6 S2'
_chemical_formula_weight         884.63
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5051(9)
_cell_length_b                   12.1557(15)
_cell_length_c                   19.520(2)
_cell_angle_alpha                101.955(4)
_cell_angle_beta                 99.056(4)
_cell_angle_gamma                92.558(4)
_cell_volume                     1943.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.91
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.563
_shelx_estimated_absorpt_T_min   0.453
_exptl_absorpt_coefficient_mu    2.244
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1590 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.7271.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.289
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            68586
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.165
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5855
_reflns_number_total             7942
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7942
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.028
_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)+(0.0390P)²+1.2620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C21, C20, C19, C18, C17, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17, C18, C19, C20, C21, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C8*(H8*), C9*(H9*), C2*(H2*), C5*(H5*), C8(H8), C5(H5), C9(H9), C14*(H14*),
 C15*(H15*), C3*(H3*), C4*(H4*), C21*(H21*), C11(H11), C11*(H11*), C4(H4),
 C2(H2), C15(H15), C12*(H12*), C12(H12), C3(H3), C14(H14), C19*(H19*), C17*(H17*
 ), C21(H21), C20*(H20*), C18*(H18*), C17(H17), C18(H18), C20(H20), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.4, Nqual =  -1, Ralpha = 0.090
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.26736(5) 0.94061(3) 0.07029(2) 0.08574(14) Uani 1 1 d . . . . .
Br1* Br 0.44324(5) 0.18234(4) 0.76584(2) 0.10329(17) Uani 1 1 d . . . . .
S2* S 1.50380(7) 0.22045(6) 0.37921(4) 0.04672(16) Uani 1 1 d . . . . .
S2 S 0.91933(8) 0.39234(8) 0.17653(5) 0.0665(2) Uani 1 1 d . . . . .
O3* O 1.5410(2) 0.16120(16) 0.31348(11) 0.0600(5) Uani 1 1 d . . . . .
O2* O 1.6245(2) 0.24348(18) 0.44139(11) 0.0614(5) Uani 1 1 d . . . . .
O1 O 0.5847(2) 0.54564(19) 0.08178(12) 0.0671(6) Uani 1 1 d . . . . .
O1* O 1.2304(2) 0.1577(2) 0.51463(11) 0.0730(6) Uani 1 1 d . . . . .
N1* N 1.3598(3) 0.1496(2) 0.40172(15) 0.0493(6) Uani 1 1 d . . . . .
O3 O 0.9697(3) 0.2812(2) 0.17097(13) 0.0817(7) Uani 1 1 d . . . . .
O2 O 1.0210(2) 0.4780(2) 0.16174(14) 0.0908(8) Uani 1 1 d . . . . .
N1 N 0.7533(3) 0.3883(3) 0.12037(15) 0.0660(7) Uani 1 1 d . . . . .
C6* C 1.0741(3) 0.1184(2) 0.39926(13) 0.0432(6) Uani 1 1 d . . . . .
C16* C 1.4256(3) 0.3476(2) 0.36618(13) 0.0426(6) Uani 1 1 d . . . . .
C1* C 1.2045(3) 0.1230(2) 0.36274(13) 0.0426(6) Uani 1 1 d . . . . .
C10* C 0.8418(3) 0.1635(2) 0.62539(14) 0.0460(6) Uani 1 1 d . . . . .
C7* C 1.0962(3) 0.1424(2) 0.47813(14) 0.0487(6) Uani 1 1 d . . . . .
C8* C 0.9559(3) 0.1475(2) 0.51394(14) 0.0505(6) Uani 1 1 d . . . . .
H8* H 0.854546 0.143275 0.486961 0.061 Uiso 1 1 calc R . . . .
C9* C 0.9702(3) 0.1580(2) 0.58300(15) 0.0503(6) Uani 1 1 d . . . . .
H9* H 1.073796 0.162481 0.607901 0.060 Uiso 1 1 calc R . . . .
C7 C 0.4616(3) 0.4939(3) 0.08811(14) 0.0521(7) Uani 1 1 d . . . . .
C6 C 0.4634(3) 0.3794(2) 0.10378(13) 0.0482(6) Uani 1 1 d . . . . .
C1 C 0.6082(3) 0.3301(3) 0.12118(14) 0.0535(7) Uani 1 1 d . . . . .
C2* C 1.1780(3) 0.1000(2) 0.28888(15) 0.0531(7) Uani 1 1 d . . . . .
H2* H 1.263749 0.103357 0.264940 0.064 Uiso 1 1 calc R . . . .
C5* C 0.9216(3) 0.0883(2) 0.35817(15) 0.0521(6) Uani 1 1 d . . . . .
H5* H 0.834261 0.083498 0.380993 0.063 Uiso 1 1 calc R . . . .
C10 C 0.1601(3) 0.7130(2) 0.06000(14) 0.0511(6) Uani 1 1 d . . . . .
C8 C 0.3098(3) 0.5488(3) 0.08186(15) 0.0554(7) Uani 1 1 d . . . . .
H8 H 0.219133 0.513462 0.091500 0.067 Uiso 1 1 calc R . . . .
C5 C 0.3217(3) 0.3167(2) 0.10321(15) 0.0561(7) Uani 1 1 d . . . . .
H5 H 0.225071 0.346909 0.091510 0.067 Uiso 1 1 calc R . . . .
C9 C 0.2999(3) 0.6465(3) 0.06300(14) 0.0552(7) Uani 1 1 d . . . . .
H9 H 0.390809 0.676496 0.050267 0.066 Uiso 1 1 calc R . . . .
C14* C 0.5632(4) 0.1454(3) 0.63590(16) 0.0610(7) Uani 1 1 d . . . . .
H14* H 0.456465 0.129420 0.614756 0.073 Uiso 1 1 calc R . . . .
C15* C 0.6816(3) 0.1400(2) 0.59488(15) 0.0549(7) Uani 1 1 d . . . . .
H15* H 0.653669 0.120077 0.545658 0.066 Uiso 1 1 calc R . . . .
C3* C 1.0256(4) 0.0721(2) 0.25088(15) 0.0593(7) Uani 1 1 d . . . . .
H3* H 1.009267 0.057536 0.201488 0.071 Uiso 1 1 calc R . . . .
C13 C -0.0937(4) 0.8476(3) 0.06534(15) 0.0578(7) Uani 1 1 d . . . . .
C4* C 0.8976(3) 0.0658(2) 0.28533(16) 0.0581(7) Uani 1 1 d . . . . .
H4* H 0.795181 0.046311 0.259376 0.070 Uiso 1 1 calc R . . . .
C13* C 0.6054(4) 0.1749(2) 0.70858(16) 0.0603(7) Uani 1 1 d . . . . .
C16 C 0.8740(3) 0.4395(3) 0.26196(17) 0.0597(7) Uani 1 1 d . U . . .
C21* C 1.4136(4) 0.3755(2) 0.30101(15) 0.0590(7) Uani 1 1 d . . . . .
H21* H 1.447386 0.327892 0.263288 0.071 Uiso 1 1 calc R . . . .
C11 C 0.0107(3) 0.6712(3) 0.06767(17) 0.0607(7) Uani 1 1 d . . . . .
H11 H -0.004112 0.596292 0.070985 0.073 Uiso 1 1 calc R . . . .
C11* C 0.8795(4) 0.1916(3) 0.69903(15) 0.0582(7) Uani 1 1 d . . . . .
H11* H 0.986007 0.206335 0.720616 0.070 Uiso 1 1 calc R . . . .
C4 C 0.3196(4) 0.2114(3) 0.11936(16) 0.0643(8) Uani 1 1 d . . . . .
H4 H 0.223022 0.171729 0.118543 0.077 Uiso 1 1 calc R . . . .
C2 C 0.6037(4) 0.2236(3) 0.13724(16) 0.0646(8) Uani 1 1 d . . . . .
H2 H 0.698811 0.191334 0.148508 0.078 Uiso 1 1 calc R . . . .
C15 C 0.1774(4) 0.8242(3) 0.05341(17) 0.0653(8) Uani 1 1 d . . . . .
H15 H 0.275308 0.853626 0.046754 0.078 Uiso 1 1 calc R . . . .
C12* C 0.7625(4) 0.1982(3) 0.74086(16) 0.0669(8) Uani 1 1 d . . . . .
H12* H 0.789342 0.218073 0.790124 0.080 Uiso 1 1 calc R . . . .
C12 C -0.1157(4) 0.7376(3) 0.07050(17) 0.0629(8) Uani 1 1 d . . . . .
H12 H -0.214824 0.708268 0.075844 0.075 Uiso 1 1 calc R . . . .
C3 C 0.4616(4) 0.1659(3) 0.13668(17) 0.0668(8) Uani 1 1 d . . . . .
H3 H 0.461105 0.095295 0.148090 0.080 Uiso 1 1 calc R . . . .
C14 C 0.0507(4) 0.8921(3) 0.05661(17) 0.0692(8) Uani 1 1 d . . . . .
H14 H 0.063663 0.966830 0.052869 0.083 Uiso 1 1 calc R . . . .
C19* C 1.3025(4) 0.5452(3) 0.3473(2) 0.0755(9) Uani 1 1 d . . . . .
H19* H 1.260638 0.612343 0.340684 0.091 Uiso 1 1 calc R . . . .
C17* C 1.3768(4) 0.4184(3) 0.42231(17) 0.0662(8) Uani 1 1 d . . . . .
H17* H 1.385449 0.399351 0.466436 0.079 Uiso 1 1 calc R . . . .
C21 C 0.9108(4) 0.3772(3) 0.31274(19) 0.0740(9) Uani 1 1 d . U . . .
H21 H 0.954828 0.308428 0.301466 0.089 Uiso 1 1 calc R . . . .
C20* C 1.3506(4) 0.4753(3) 0.29236(19) 0.0754(9) Uani 1 1 d . . . . .
H20* H 1.341050 0.494791 0.248344 0.091 Uiso 1 1 calc R . . . .
C18* C 1.3146(4) 0.5182(3) 0.4122(2) 0.0789(10) Uani 1 1 d . . . . .
H18* H 1.281132 0.566745 0.449604 0.095 Uiso 1 1 calc R . . . .
C17 C 0.8062(4) 0.5409(3) 0.2782(2) 0.0853(10) Uani 1 1 d . U . . .
H17 H 0.779939 0.582422 0.243656 0.102 Uiso 1 1 calc R . . . .
C18 C 0.7778(5) 0.5796(4) 0.3464(3) 0.1056(13) Uani 1 1 d . U . . .
H18 H 0.731754 0.647424 0.358118 0.127 Uiso 1 1 calc R . . . .
C20 C 0.8816(5) 0.4176(4) 0.3806(2) 0.0946(12) Uani 1 1 d . U . . .
H20 H 0.905891 0.375780 0.415176 0.113 Uiso 1 1 calc R . . . .
C19 C 0.8181(5) 0.5172(4) 0.3970(2) 0.1029(13) Uani 1 1 d . U . . .
H19 H 0.801188 0.544310 0.443216 0.124 Uiso 1 1 calc R . . . .
H1* H 1.366(3) 0.161(3) 0.4409(16) 0.052(10) Uiso 1 1 d . . . . .
H1 H 0.751(3) 0.448(2) 0.1124(15) 0.044(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Br1 C13 1.902(3) . ?
Br1* C13* 1.901(3) . ?
S2* O3* 1.425(2) . ?
S2* O2* 1.431(2) . ?
S2* N1* 1.633(2) . ?
S2* C16* 1.760(2) . ?
S2 O3 1.424(2) . ?
S2 O2 1.428(2) . ?
S2 N1 1.638(3) . ?
S2 C16 1.756(3) . ?
O1 C7 1.233(3) . ?
O1* C7* 1.230(3) . ?
N1* C1* 1.404(3) . ?
N1* H1* 0.74(3) . ?
N1 C1 1.399(4) . ?
N1 H1 0.78(3) . ?
C6* C1* 1.414(3) . ?
C6* C7* 1.486(4) . ?
C6* C5* 1.403(4) . ?
C16* C21* 1.373(4) . ?
C16* C17* 1.378(4) . ?
C1* C2* 1.390(4) . ?
C10* C9* 1.466(4) . ?
C10* C15* 1.391(4) . ?
C10* C11* 1.388(4) . ?
C7* C8* 1.473(4) . ?
C8* H8* 0.9300 . ?
C8* C9* 1.313(4) . ?
C9* H9* 0.9300 . ?
C7 C6 1.487(4) . ?
C7 C8 1.479(4) . ?
C6 C1 1.417(4) . ?
C6 C5 1.394(4) . ?
C1 C2 1.394(4) . ?
C2* H2* 0.9300 . ?
C2* C3* 1.378(4) . ?
C5* H5* 0.9300 . ?
C5* C4* 1.371(4) . ?
C10 C9 1.467(4) . ?
C10 C11 1.389(4) . ?
C10 C15 1.387(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.317(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.380(4) . ?
C9 H9 0.9300 . ?
C14* H14* 0.9300 . ?
C14* C15* 1.377(4) . ?
C14* C13* 1.374(4) . ?
C15* H15* 0.9300 . ?
C3* H3* 0.9300 . ?
C3* C4* 1.374(4) . ?
C13 C12 1.368(4) . ?
C13 C14 1.369(4) . ?
C4* H4* 0.9300 . ?
C13* C12* 1.374(4) . ?
C16 C21 1.374(4) . ?
C16 C17 1.383(5) . ?
C21* H21* 0.9300 . ?
C21* C20* 1.379(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(4) . ?
C11* H11* 0.9300 . ?
C11* C12* 1.378(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.388(4) . ?
C12* H12* 0.9300 . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C19* H19* 0.9300 . ?
C19* C20* 1.353(5) . ?
C19* C18* 1.363(5) . ?
C17* H17* 0.9300 . ?
C17* C18* 1.383(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.379(5) . ?
C20* H20* 0.9300 . ?
C18* H18* 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.379(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(6) . ?
C20 H20 0.9300 . ?
C20 C19 1.347(6) . ?
C19 H19 0.9300 . ?

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
O3* S2* O2* 119.46(12) . . ?
O3* S2* N1* 109.86(13) . . ?
O3* S2* C16* 108.34(12) . . ?
O2* S2* N1* 103.78(13) . . ?
O2* S2* C16* 109.17(12) . . ?
N1* S2* C16* 105.31(12) . . ?
O3 S2 O2 119.34(14) . . ?
O3 S2 N1 109.07(16) . . ?
O3 S2 C16 108.53(14) . . ?
O2 S2 N1 104.10(15) . . ?
O2 S2 C16 108.41(16) . . ?
N1 S2 C16 106.68(14) . . ?
S2* N1* H1* 111(2) . . ?
C1* N1* S2* 125.5(2) . . ?
C1* N1* H1* 116(2) . . ?
S2 N1 H1 105(2) . . ?
C1 N1 S2 125.9(2) . . ?
C1 N1 H1 118(2) . . ?
C1* C6* C7* 121.9(2) . . ?
C5* C6* C1* 117.5(2) . . ?
C5* C6* C7* 120.6(2) . . ?
C21* C16* S2* 120.4(2) . . ?
C21* C16* C17* 120.6(3) . . ?
C17* C16* S2* 119.0(2) . . ?
N1* C1* C6* 119.4(2) . . ?
C2* C1* N1* 120.8(2) . . ?
C2* C1* C6* 119.8(2) . . ?
C15* C10* C9* 122.6(2) . . ?
C11* C10* C9* 119.6(2) . . ?
C11* C10* C15* 117.8(2) . . ?
O1* C7* C6* 121.3(2) . . ?
O1* C7* C8* 118.8(2) . . ?
C8* C7* C6* 119.9(2) . . ?
C7* C8* H8* 119.2 . . ?
C9* C8* C7* 121.7(2) . . ?
C9* C8* H8* 119.2 . . ?
C10* C9* H9* 116.3 . . ?
C8* C9* C10* 127.5(3) . . ?
C8* C9* H9* 116.3 . . ?
O1 C7 C6 121.5(2) . . ?
O1 C7 C8 119.0(3) . . ?
C8 C7 C6 119.5(2) . . ?
C1 C6 C7 121.7(3) . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 C1 117.2(3) . . ?
N1 C1 C6 119.3(3) . . ?
C2 C1 N1 121.1(3) . . ?
C2 C1 C6 119.6(3) . . ?
C1* C2* H2* 119.7 . . ?
C3* C2* C1* 120.5(3) . . ?
C3* C2* H2* 119.7 . . ?
C6* C5* H5* 119.1 . . ?
C4* C5* C6* 121.9(3) . . ?
C4* C5* H5* 119.1 . . ?
C11 C10 C9 122.5(3) . . ?
C15 C10 C9 119.6(3) . . ?
C15 C10 C11 117.8(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C6 C5 H5 118.8 . . ?
C4 C5 C6 122.4(3) . . ?
C4 C5 H5 118.8 . . ?
C10 C9 H9 116.7 . . ?
C8 C9 C10 126.7(3) . . ?
C8 C9 H9 116.7 . . ?
C15* C14* H14* 120.6 . . ?
C13* C14* H14* 120.6 . . ?
C13* C14* C15* 118.9(3) . . ?
C10* C15* H15* 119.2 . . ?
C14* C15* C10* 121.5(3) . . ?
C14* C15* H15* 119.2 . . ?
C2* C3* H3* 119.7 . . ?
C4* C3* C2* 120.5(3) . . ?
C4* C3* H3* 119.7 . . ?
C12 C13 Br1 119.3(2) . . ?
C12 C13 C14 121.3(3) . . ?
C14 C13 Br1 119.3(2) . . ?
C5* C4* C3* 119.7(3) . . ?
C5* C4* H4* 120.1 . . ?
C3* C4* H4* 120.1 . . ?
C14* C13* Br1* 119.3(2) . . ?
C14* C13* C12* 121.5(3) . . ?
C12* C13* Br1* 119.2(2) . . ?
C21 C16 S2 119.8(3) . . ?
C21 C16 C17 120.5(3) . . ?
C17 C16 S2 119.7(3) . . ?
C16* C21* H21* 120.5 . . ?
C16* C21* C20* 119.0(3) . . ?
C20* C21* H21* 120.5 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C10* C11* H11* 119.3 . . ?
C12* C11* C10* 121.5(3) . . ?
C12* C11* H11* 119.3 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C10 C15 H15 119.5 . . ?
C10 C15 C14 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C13* C12* C11* 118.9(3) . . ?
C13* C12* H12* 120.5 . . ?
C11* C12* H12* 120.5 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C20* C19* H19* 119.6 . . ?
C20* C19* C18* 120.7(3) . . ?
C18* C19* H19* 119.6 . . ?
C16* C17* H17* 120.4 . . ?
C16* C17* C18* 119.1(3) . . ?
C18* C17* H17* 120.4 . . ?
C16 C21 H21 120.3 . . ?
C16 C21 C20 119.3(4) . . ?
C20 C21 H21 120.3 . . ?
C21* C20* H20* 119.7 . . ?
C19* C20* C21* 120.6(3) . . ?
C19* C20* H20* 119.7 . . ?
C19* C18* C17* 119.9(3) . . ?
C19* C18* H18* 120.1 . . ?
C17* C18* H18* 120.1 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(4) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.4(4) . . ?
C19 C20 H20 119.8 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(4) . . ?
C20 C19 H19 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_G23_3_0ma
_audit_block_doi                 10.5517/ccdc.csd.cc20353f
_database_code_depnum_ccdc_archive 'CCDC 1850083'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.cplett.2019.136852 2019
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2018-06-18 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C21 H16 Br N O3 S'
_chemical_formula_sum            'C21 H16 Br N O3 S'
_chemical_formula_weight         442.34
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.8047(12)
_cell_length_b                   7.5462(7)
_cell_length_c                   18.9025(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.055(3)
_cell_angle_gamma                90
_cell_volume                     1910.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.12
_exptl_absorpt_coefficient_mu    2.282
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0902 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.5876.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_description       prism
_exptl_crystal_density_diffrn    1.5380
_exptl_crystal_F_000             895.7594
_exptl_crystal_size_max          0.831
_exptl_crystal_size_mid          0.563
_exptl_crystal_size_min          0.462
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            52509
_diffrn_reflns_theta_full        26.4344
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         1.65
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -17
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              -11
_reflns_number_gt                3318
_reflns_number_total             3940
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.6005
_refine_diff_density_min         -0.5137
_refine_diff_density_rms         0.0617
_refine_ls_d_res_high            0.7983
_refine_ls_d_res_low             12.3349
_refine_ls_goodness_of_fit_ref   1.0514
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.0514
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+1.1990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0778
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C6AA(H6AA), C7AA(H7AA), C8AA(H8AA), N1AA(H1AA), C0BA(H0BA),
 C1BA(H1BA), C2BA(H2BA), C3BA(H3BA), C4BA(H4BA), C8BA(H8BA), C9BA(H9BA),
 C0CA(H0CA), C2(H2), C1(H1), C5BA(H5BA)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Br Br 0.432338(19) 0.43683(4) 0.146836(13) 0.06104(11) Uani 1.000000 .
S S -0.21863(4) 0.64913(7) 0.04793(3) 0.03809(13) Uani 1.000000 .
C5AA C -0.10292(15) 0.5536(3) 0.18097(11) 0.0356(4) Uani 1.000000 .
C9AA C -0.26717(16) 0.4368(3) 0.02348(10) 0.0385(5) Uani 1.000000 .
C1AA C -0.00471(14) 0.5272(3) 0.22356(11) 0.0349(4) Uani 1.000000 .
C2AA C 0.36826(15) 0.5699(3) 0.27047(11) 0.0374(4) Uani 1.000000 .
O0AA O -0.28887(12) 0.7423(2) 0.07817(9) 0.0537(4) Uani 1.000000 .
C3AA C 0.45010(15) 0.5149(3) 0.24463(12) 0.0401(5) Uani 1.000000 .
O O -0.18669(12) 0.7236(2) -0.01220(8) 0.0534(4) Uani 1.000000 .
C4AA C 0.08418(15) 0.5741(3) 0.19583(12) 0.0405(5) Uani 1.000000 .
C0AA C 0.18353(16) 0.5749(3) 0.24706(12) 0.0455(5) Uani 1.000000 .
H0AA H 0.18773(16) 0.5798(3) 0.29688(12) 0.0546(6) Uiso 1.000000 R
O5AA O 0.07672(11) 0.6130(3) 0.13164(9) 0.0563(5) Uani 1.000000 .
C6AA C 0.00745(16) 0.4551(3) 0.29301(12) 0.0421(5) Uani 1.000000 .
H6AA H 0.07173(16) 0.4352(3) 0.32125(12) 0.0506(6) Uiso 1.000000 R
C7AA C 0.26635(15) 0.5688(3) 0.22451(12) 0.0404(5) Uani 1.000000 .
H7AA H 0.25949(15) 0.5633(3) 0.17438(12) 0.0485(6) Uiso 1.000000 R
C8AA C -0.16754(16) 0.4453(3) 0.28009(13) 0.0502(6) Uani 1.000000 .
H8AA H -0.22189(16) 0.4202(3) 0.29938(13) 0.0602(7) Uiso 1.000000 R
N1AA N -0.11602(13) 0.6202(3) 0.11019(10) 0.0453(5) Uani 1.000000 .
H1AA H -0.06215(13) 0.6500(3) 0.09801(10) 0.0544(5) Uiso 1.000000 R
C0BA C -0.07263(17) 0.4125(3) 0.32116(12) 0.0486(6) Uani 1.000000 .
H0BA H -0.06264(17) 0.3621(3) 0.36729(12) 0.0583(7) Uiso 1.000000 R
C1BA C 0.54620(17) 0.5155(4) 0.28799(15) 0.0549(6) Uani 1.000000 .
H1BA H 0.59913(17) 0.4777(4) 0.26933(15) 0.0659(7) Uiso 1.000000 R
C2BA C -0.18362(15) 0.5149(3) 0.21082(12) 0.0457(5) Uani 1.000000 .
H2BA H -0.24845(15) 0.5361(3) 0.18385(12) 0.0548(6) Uiso 1.000000 R
C3BA C 0.4846(2) 0.6289(4) 0.38657(14) 0.0585(6) Uani 1.000000 .
H3BA H 0.4961(2) 0.6675(4) 0.43462(14) 0.0702(8) Uiso 1.000000 R
C4BA C -0.21883(19) 0.3277(3) -0.01557(12) 0.0519(6) Uani 1.000000 .
H4BA H -0.16132(19) 0.3654(3) -0.02849(12) 0.0622(7) Uiso 1.000000 R
C8BA C 0.56310(19) 0.5726(4) 0.35922(15) 0.0634(7) Uani 1.000000 .
H8BA H 0.62764(19) 0.5731(4) 0.38883(15) 0.0761(9) Uiso 1.000000 R
C9BA C 0.38903(17) 0.6281(3) 0.34287(12) 0.0467(5) Uani 1.000000 .
H9BA H 0.33679(17) 0.6673(3) 0.36199(12) 0.0560(6) Uiso 1.000000 R
C0CA C -0.3533(2) 0.3821(4) 0.04178(14) 0.0597(7) Uani 1.000000 .
H0CA H -0.3858(2) 0.4567(4) 0.06771(14) 0.0716(8) Uiso 1.000000 R
C2 C -0.3432(3) 0.1067(4) -0.01619(19) 0.0861(11) Uani 1.000000 .
H2 H -0.3685(3) -0.0061(4) -0.02924(19) 0.1033(13) Uiso 1.000000 R
C1 C -0.2580(3) 0.1609(4) -0.03500(15) 0.0759(9) Uani 1.000000 .
H1 H -0.2264(3) 0.0851(4) -0.06102(15) 0.0910(11) Uiso 1.000000 R
C5BA C -0.3907(3) 0.2155(5) 0.02116(18) 0.0852(10) Uani 1.000000 .
H5BA H -0.4489(3) 0.1778(5) 0.03300(18) 0.1023(12) Uiso 1.000000 R


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
Br C3AA 1.898(2) . ?
S C9AA 1.755(2) . ?
S O0AA 1.4248(16) . ?
S O 1.4304(15) . ?
S N1AA 1.6215(18) . ?
C5AA C1AA 1.413(3) . ?
C5AA N1AA 1.399(3) . ?
C5AA C2BA 1.397(3) . ?
C9AA C4BA 1.381(3) . ?
C9AA C0CA 1.380(3) . ?
C1AA C4AA 1.489(3) . ?
C1AA C6AA 1.393(3) . ?
C2AA C3AA 1.398(3) . ?
C2AA C7AA 1.463(3) . ?
C2AA C9BA 1.399(3) . ?
C3AA C1BA 1.380(3) . ?
C4AA C0AA 1.474(3) . ?
C4AA O5AA 1.228(3) . ?
C0AA C7AA 1.315(3) . ?
C6AA C0BA 1.377(3) . ?
C8AA C0BA 1.374(3) . ?
C8AA C2BA 1.378(3) . ?
C1BA C8BA 1.378(4) . ?
C3BA C8BA 1.377(4) . ?
C3BA C9BA 1.376(3) . ?
C4BA C1 1.384(4) . ?
C0CA C5BA 1.379(4) . ?
C2 C1 1.371(5) . ?
C2 C5BA 1.352(5) . ?

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
O0AA S C9AA 107.61(10) . . ?
O S C9AA 108.75(10) . . ?
O S O0AA 119.74(10) . . ?
N1AA S C9AA 106.18(10) . . ?
N1AA S O0AA 109.56(10) . . ?
N1AA S O 104.24(10) . . ?
N1AA C5AA C1AA 118.61(17) . . ?
C2BA C5AA C1AA 119.32(19) . . ?
C2BA C5AA N1AA 122.07(19) . . ?
C4BA C9AA S 118.81(18) . . ?
C0CA C9AA S 120.28(19) . . ?
C0CA C9AA C4BA 120.9(2) . . ?
C4AA C1AA C5AA 121.65(18) . . ?
C6AA C1AA C5AA 118.13(18) . . ?
C6AA C1AA C4AA 120.22(18) . . ?
C7AA C2AA C3AA 122.2(2) . . ?
C9BA C2AA C3AA 116.35(19) . . ?
C9BA C2AA C7AA 121.45(19) . . ?
C2AA C3AA Br 120.53(16) . . ?
C1BA C3AA Br 117.24(17) . . ?
C1BA C3AA C2AA 122.2(2) . . ?
C0AA C4AA C1AA 118.97(19) . . ?
O5AA C4AA C1AA 121.72(19) . . ?
O5AA C4AA C0AA 119.31(18) . . ?
C7AA C0AA C4AA 122.0(2) . . ?
C0BA C6AA C1AA 122.1(2) . . ?
C0AA C7AA C2AA 126.4(2) . . ?
C2BA C8AA C0BA 121.2(2) . . ?
C5AA N1AA S 129.01(14) . . ?
C8AA C0BA C6AA 119.0(2) . . ?
C8BA C1BA C3AA 119.4(2) . . ?
C8AA C2BA C5AA 120.2(2) . . ?
C9BA C3BA C8BA 120.0(2) . . ?
C1 C4BA C9AA 118.4(3) . . ?
C3BA C8BA C1BA 120.1(2) . . ?
C3BA C9BA C2AA 121.8(2) . . ?
C5BA C0CA C9AA 119.2(3) . . ?
C5BA C2 C1 120.6(3) . . ?
C2 C1 C4BA 120.5(3) . . ?
C2 C5BA C0CA 120.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
(E)-3-(2-bromophenyl)-1-(2phenylsulfonylamine)-phenyl)prop-2-en-1-one
_chemical_name_common            'bromine chalcone'
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g241_ueg2
_database_code_depnum_ccdc_archive 'CCDC 1949073'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2019-08-24 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O4 S'
_chemical_formula_sum            'C23 H21 N O4 S'
_chemical_formula_weight         407.47
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   8.8384(5)
_cell_length_b                   26.6514(16)
_cell_length_c                   8.7741(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.963(5)
_cell_angle_gamma                90
_cell_volume                     2066.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17671
_cell_measurement_temperature    293.7(7)
_cell_measurement_theta_max      27.0210
_cell_measurement_theta_min      3.8790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            71464
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         3.264
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.7(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  98.00   1.00    8.44    --   11.26-178.00  60.00   64
  2  ω     34.00  98.00   1.00    8.44    --   11.26-178.00 120.00   64
  3  ω     34.00  98.00   1.00    8.44    --   11.26-178.00  90.00   64
  4  ω    -40.00  62.00   1.00    8.44    --  -11.49  57.00-120.00  102
  5  ω    -84.00  17.00   1.00    8.44    --  -11.49 -57.00  90.00  101
  6  ω    -20.00  29.00   1.00    8.44    --  -11.49 -99.00-150.00   49
  7  ω    -65.00  44.00   1.00    8.44    --   11.26 -77.00 150.00  109
  8  ω    -17.00  84.00   1.00    8.44    --   11.26  57.00 -90.00  101
  9  ω    -20.00  29.00   1.00    8.44    --  -11.49 -99.00 -30.00   49
 10  ω    -87.00 -40.00   1.00    8.44    --  -11.49 155.00-133.00   47
 11  ω    -86.00  13.00   1.00    8.44    --  -11.49 -38.00 -60.00   99
 12  ω    -20.00  52.00   1.00    8.44    --   11.26 -99.00  60.00   72
 13  ω    -20.00  52.00   1.00    8.44    --   11.26 -99.00-150.00   72
 14  ω    -20.00  52.00   1.00    8.44    --   11.26 -99.00  30.00   72
 15  ω     18.00  88.00   1.00    8.44    --   11.26-155.00-171.00   70
 16  ω    -20.00  29.00   1.00    8.44    --  -11.49 -99.00 120.00   49
 17  ω    -65.00  44.00   1.00    8.44    --   11.26 -77.00-120.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0391594000
_diffrn_orient_matrix_UB_12      -0.0231450000
_diffrn_orient_matrix_UB_13      0.0052101000
_diffrn_orient_matrix_UB_21      0.0700476000
_diffrn_orient_matrix_UB_22      -0.0128871000
_diffrn_orient_matrix_UB_23      0.0062761000
_diffrn_orient_matrix_UB_31      -0.0014820000
_diffrn_orient_matrix_UB_32      0.0025001000
_diffrn_orient_matrix_UB_33      0.0804771000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4391
_reflns_number_total             5570
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.110
_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)+(0.0410P)²+0.9010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C2(H2), C5(H5), C14(H14), C3(H3), C11(H11),
 C15(H15), C4(H4), C21(H21), C18(H18), C17(H17), C20(H20), C19(H19)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50869(6) 0.34296(2) 0.40769(5) 0.04722(14) Uani 1 1 d . . . . .
N0AA N 0.4584(2) 0.37750(6) 0.55209(18) 0.0499(4) Uani 1 1 d . . . . .
O1 O 0.61684(18) 0.44077(6) 0.71476(16) 0.0647(4) Uani 1 1 d . . . . .
C6 C 0.45373(19) 0.38119(7) 0.8297(2) 0.0429(4) Uani 1 1 d . . . . .
O4 O 0.95419(17) 0.58425(5) 1.49663(16) 0.0614(4) Uani 1 1 d . . . . .
O2 O 0.57666(19) 0.37769(5) 0.30492(15) 0.0637(4) Uani 1 1 d . . . . .
O3 O 0.38276(16) 0.31373(6) 0.35528(16) 0.0614(4) Uani 1 1 d . . . . .
C16 C 0.6498(2) 0.30229(7) 0.4786(2) 0.0475(4) Uani 1 1 d . . . . .
C1 C 0.40584(19) 0.35842(7) 0.6917(2) 0.0432(4) Uani 1 1 d . . . . .
C8 C 0.6197(2) 0.44269(7) 0.9811(2) 0.0522(5) Uani 1 1 d . . . . .
H8 H 0.582241 0.428891 1.070163 0.063 Uiso 1 1 calc R . . . .
C9 C 0.7195(2) 0.47959(7) 0.9906(2) 0.0504(4) Uani 1 1 d . . . . .
H9 H 0.756494 0.491244 0.898497 0.060 Uiso 1 1 calc R . . . .
C12 C 0.7856(2) 0.51873(7) 1.4002(2) 0.0511(4) Uani 1 1 d . . . . .
H12 H 0.751306 0.510637 1.496785 0.061 Uiso 1 1 calc R . . . .
C2 C 0.3050(2) 0.31841(7) 0.6935(2) 0.0516(4) Uani 1 1 d . . . . .
H2 H 0.274201 0.303416 0.602461 0.062 Uiso 1 1 calc R . . . .
C10 C 0.7786(2) 0.50428(7) 1.1274(2) 0.0464(4) Uani 1 1 d . . . . .
C13 C 0.8938(2) 0.55599(7) 1.3825(2) 0.0482(4) Uani 1 1 d . . . . .
C5 C 0.3928(2) 0.36276(8) 0.9645(2) 0.0516(4) Uani 1 1 d . . . . .
H5 H 0.420468 0.377728 1.056613 0.062 Uiso 1 1 calc R . . . .
C7 C 0.5667(2) 0.42299(7) 0.8335(2) 0.0475(4) Uani 1 1 d . . . . .
C14 C 0.9467(2) 0.56626(7) 1.2385(2) 0.0555(5) Uani 1 1 d . . . . .
H14 H 1.021221 0.590486 1.225952 0.067 Uiso 1 1 calc R . . . .
C3 C 0.2506(2) 0.30088(8) 0.8297(2) 0.0549(5) Uani 1 1 d . . . . .
H3 H 0.184430 0.273748 0.830069 0.066 Uiso 1 1 calc R . . . .
C11 C 0.7292(2) 0.49376(7) 1.2735(2) 0.0508(4) Uani 1 1 d . . . . .
H11 H 0.655962 0.469146 1.286326 0.061 Uiso 1 1 calc R . . . .
C15 C 0.8900(2) 0.54095(7) 1.1139(2) 0.0551(5) Uani 1 1 d . . . . .
H15 H 0.926923 0.548456 1.017968 0.066 Uiso 1 1 calc R . . . .
C22 C 0.9017(3) 0.57736(8) 1.6478(2) 0.0580(5) Uani 1 1 d . . . . .
H22A H 0.928518 0.544214 1.685040 0.070 Uiso 1 1 calc R . . . .
H22B H 0.792558 0.580969 1.650482 0.070 Uiso 1 1 calc R . . . .
C4 C 0.2932(2) 0.32312(8) 0.9651(2) 0.0549(5) Uani 1 1 d . . . . .
H4 H 0.254808 0.311443 1.056576 0.066 Uiso 1 1 calc R . . . .
C21 C 0.6311(3) 0.25160(9) 0.4741(3) 0.0799(8) Uani 1 1 d . . . . .
H21 H 0.543266 0.237676 0.432258 0.096 Uiso 1 1 calc R . . . .
C23 C 0.9773(3) 0.61715(9) 1.7440(3) 0.0773(7) Uani 1 1 d . . . . .
H23A H 0.955362 0.649618 1.701687 0.116 Uiso 1 1 calc GR . . . .
H23B H 1.084753 0.611794 1.745583 0.116 Uiso 1 1 calc GR . . . .
H23C H 0.940132 0.615432 1.846014 0.116 Uiso 1 1 calc GR . . . .
C18 C 0.8916(3) 0.29238(14) 0.5939(4) 0.1062(11) Uani 1 1 d . . . . .
H18 H 0.980732 0.306067 0.633422 0.127 Uiso 1 1 calc R . . . .
C17 C 0.7798(3) 0.32328(10) 0.5392(3) 0.0768(7) Uani 1 1 d . . . . .
H17 H 0.791375 0.357940 0.542892 0.092 Uiso 1 1 calc R . . . .
C20 C 0.7447(4) 0.22111(11) 0.5327(5) 0.1104(12) Uani 1 1 d . . . . .
H20 H 0.732839 0.186442 0.531983 0.133 Uiso 1 1 calc R . . . .
C19 C 0.8730(3) 0.24171(14) 0.5909(4) 0.1085(11) Uani 1 1 d . . . . .
H19 H 0.949343 0.221027 0.629317 0.130 Uiso 1 1 calc R . . . .
H0AA H 0.518(3) 0.4024(9) 0.562(2) 0.060(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S1 N0AA 1.6338(16) . ?
S1 O2 1.4313(14) . ?
S1 O3 1.4283(14) . ?
S1 C16 1.7584(19) . ?
N0AA C1 1.412(2) . ?
O1 C7 1.234(2) . ?
C6 C1 1.413(2) . ?
C6 C5 1.397(3) . ?
C6 C7 1.496(3) . ?
O4 C13 1.355(2) . ?
O4 C22 1.425(2) . ?
C16 C21 1.362(3) . ?
C16 C17 1.377(3) . ?
C1 C2 1.390(3) . ?
C8 C9 1.322(3) . ?
C8 C7 1.467(3) . ?
C9 C10 1.458(3) . ?
C12 C13 1.389(3) . ?
C12 C11 1.382(3) . ?
C2 C3 1.377(3) . ?
C10 C11 1.390(3) . ?
C10 C15 1.393(3) . ?
C13 C14 1.382(3) . ?
C5 C4 1.375(3) . ?
C14 C15 1.372(3) . ?
C3 C4 1.375(3) . ?
C22 C23 1.505(3) . ?
C21 C20 1.384(4) . ?
C18 C17 1.367(4) . ?
C18 C19 1.361(5) . ?
C20 C19 1.352(5) . ?

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
N0AA S1 C16 105.87(9) . . ?
O2 S1 N0AA 104.29(9) . . ?
O2 S1 C16 108.60(9) . . ?
O3 S1 N0AA 109.64(9) . . ?
O3 S1 O2 118.87(9) . . ?
O3 S1 C16 108.78(9) . . ?
C1 N0AA S1 124.59(13) . . ?
C1 C6 C7 121.92(16) . . ?
C5 C6 C1 117.42(17) . . ?
C5 C6 C7 120.65(16) . . ?
C13 O4 C22 119.07(16) . . ?
C21 C16 S1 121.06(16) . . ?
C21 C16 C17 121.0(2) . . ?
C17 C16 S1 117.95(16) . . ?
N0AA C1 C6 119.40(16) . . ?
C2 C1 N0AA 120.42(16) . . ?
C2 C1 C6 120.16(17) . . ?
C9 C8 C7 121.64(19) . . ?
C8 C9 C10 128.10(19) . . ?
C11 C12 C13 119.59(18) . . ?
C3 C2 C1 120.23(18) . . ?
C11 C10 C9 123.66(17) . . ?
C11 C10 C15 116.93(17) . . ?
C15 C10 C9 119.41(18) . . ?
O4 C13 C12 125.31(18) . . ?
O4 C13 C14 115.47(17) . . ?
C14 C13 C12 119.21(17) . . ?
C4 C5 C6 121.95(18) . . ?
O1 C7 C6 121.10(16) . . ?
O1 C7 C8 119.60(18) . . ?
C8 C7 C6 119.29(17) . . ?
C15 C14 C13 120.40(18) . . ?
C4 C3 C2 120.61(19) . . ?
C12 C11 C10 122.05(18) . . ?
C14 C15 C10 121.78(19) . . ?
O4 C22 C23 106.42(18) . . ?
C3 C4 C5 119.61(19) . . ?
C16 C21 C20 119.0(2) . . ?
C19 C18 C17 120.3(3) . . ?
C18 C17 C16 119.0(3) . . ?
C19 C20 C21 120.0(3) . . ?
C20 C19 C18 120.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.383
_oxdiff_exptl_absorpt_empirical_full_min 0.745
