# 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.
#
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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 \w and \f-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 > 2\s(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/[\s^2^(Fo^2^)+(0.0516P)^2^+0.6910P] where P=(Fo^2^+2Fc^2^)/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 . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0355(2) 0.0430(2) 0.0368(2) 0.00577(16) -0.01276(17) -0.00034(16)
Cl1 0.0443(3) 0.1156(5) 0.0498(3) -0.0019(3) -0.0163(2) 0.0190(3)
C10 0.0300(8) 0.0420(8) 0.0416(8) -0.0020(7) -0.0159(7) -0.0004(6)
C6 0.0343(8) 0.0432(9) 0.0449(9) 0.0073(7) -0.0195(7) -0.0046(7)
N1 0.0315(7) 0.0677(10) 0.0413(8) 0.0077(7) -0.0151(6) -0.0122(7)
C16 0.0393(8) 0.0458(9) 0.0317(8) 0.0069(6) -0.0160(7) -0.0021(7)
O1 0.0315(6) 0.0991(11) 0.0540(8) 0.0161(7) -0.0177(6) -0.0116(7)
C15 0.0317(8) 0.0424(8) 0.0373(8) 0.0004(6) -0.0137(6) -0.0022(6)
O2 0.0516(7) 0.0565(8) 0.0549(7) 0.0002(6) -0.0195(6) 0.0161(6)
C9 0.0322(8) 0.0505(9) 0.0497(10) 0.0001(8) -0.0189(7) -0.0014(7)
O3 0.0521(7) 0.0582(8) 0.0472(7) 0.0157(6) -0.0134(6) -0.0131(6)
C11 0.0395(9) 0.0606(11) 0.0450(9) 0.0055(8) -0.0225(7) -0.0024(8)
C8 0.0349(8) 0.0648(11) 0.0485(10) -0.0022(8) -0.0200(8) -0.0029(8)
C1 0.0372(8) 0.0527(10) 0.0466(9) 0.0100(8) -0.0204(7) -0.0022(7)
C14 0.0313(8) 0.0724(12) 0.0440(9) 0.0078(8) -0.0183(7) -0.0059(8)
C12 0.0400(9) 0.0730(12) 0.0419(9) 0.0139(9) -0.0158(8) -0.0095(9)
C5 0.0453(10) 0.0535(10) 0.0517(10) -0.0003(8) -0.0220(8) -0.0019(8)
C21 0.0563(11) 0.0557(11) 0.0438(9) 0.0003(8) -0.0226(9) 0.0119(9)
C13 0.0299(8) 0.0803(14) 0.0479(10) 0.0118(9) -0.0143(7) -0.0108(8)
C2 0.0480(10) 0.0730(13) 0.0684(13) 0.0109(10) -0.0365(10) 0.0026(9)
C4 0.0729(14) 0.0684(13) 0.0524(11) -0.0037(9) -0.0353(10) -0.0034(11)
C20 0.121(2) 0.0553(12) 0.0580(13) -0.0093(10) -0.0488(14) 0.0278(13)
C17 0.0459(10) 0.0747(13) 0.0545(11) 0.0024(10) -0.0201(9) -0.0123(9)
C18 0.0875(18) 0.0870(18) 0.0780(16) 0.0108(14) -0.0415(14) -0.0406(15)
C19 0.138(3) 0.0565(14) 0.0775(16) 0.0137(12) -0.0655(18) -0.0299(16)
C3 0.0789(15) 0.0773(14) 0.0708(14) 0.0051(11) -0.0552(13) -0.0021(12)
C7 0.0357(8) 0.0512(10) 0.0462(9) 0.0056(7) -0.0199(7) -0.0027(7)
_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
_shelx_res_file
;
TITL new in P21/c #14
shelx.res
created by SHELXL-2016/6 at 10:58:56 on 30-Apr-2018
REM reset to P21/c #14
CELL 0.71073 13.7952 7.584 20.2728 90 62.896 90
ZERR 4 0.0007 0.0004 0.0009 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O S Cl N
UNIT 84 64 12 4 4 4
EQIV $1 x,1/2-y,-1/2+z
EQIV $2 -x,1-y,1-z
EQIV $3 1-x,1/2+y,1/2-z
HTAB C5 O3_$1
HTAB C21 O1_$2
HTAB C12 O2_$3
HTAB C13 O2_$3
L.S. 4
PLAN 20
SIZE 0.336 0.457 0.736
TEMP 23
BOND
CONF
fmap 2
acta
REM
REM
REM
WGHT 0.051600 0.691000
FVAR 0.12296
S1 4 0.266755 0.346830 0.454870 11.00000 0.03553 0.04304 =
0.03685 0.00577 -0.01276 -0.00034
CL1 5 -0.281569 0.563076 0.351384 11.00000 0.04426 0.11563 =
0.04976 -0.00190 -0.01627 0.01899
C10 1 0.226381 0.468688 0.278308 11.00000 0.02997 0.04195 =
0.04164 -0.00202 -0.01592 -0.00039
C6 1 -0.101578 0.435691 0.233189 11.00000 0.03429 0.04322 =
0.04494 0.00732 -0.01947 -0.00461
N1 6 0.224574 0.375668 0.393010 11.00000 0.03149 0.06771 =
0.04134 0.00770 -0.01510 -0.01223
H1 2 0.157062 0.369057 0.408517 11.00000 -1.20000
C16 1 0.295725 0.558122 0.477173 11.00000 0.03930 0.04585 =
0.03170 0.00688 -0.01602 -0.00211
O1 3 0.051433 0.391868 0.373363 11.00000 0.03148 0.09912 =
0.05403 0.01608 -0.01774 -0.01158
C15 1 0.282496 0.441115 0.320787 11.00000 0.03170 0.04239 =
0.03730 0.00045 -0.01367 -0.00224
O2 3 0.365870 0.249455 0.423735 11.00000 0.05156 0.05647 =
0.05486 0.00024 -0.01952 0.01612
C9 1 0.108710 0.426119 0.307788 11.00000 0.03216 0.05048 =
0.04971 0.00009 -0.01885 -0.00136
O3 3 0.174273 0.277448 0.517409 11.00000 0.05213 0.05820 =
0.04721 0.01566 -0.01339 -0.01311
C11 1 0.283770 0.540723 0.207701 11.00000 0.03952 0.06055 =
0.04501 0.00553 -0.02247 -0.00244
AFIX 43
H11 2 0.247139 0.562251 0.179722 11.00000 -1.20000
AFIX 0
C8 1 0.060329 0.423443 0.256039 11.00000 0.03485 0.06484 =
0.04848 -0.00224 -0.02003 -0.00285
AFIX 43
H8 2 0.105819 0.411022 0.205555 11.00000 -1.20000
AFIX 0
C1 1 -0.209710 0.489983 0.260500 11.00000 0.03718 0.05275 =
0.04663 0.00998 -0.02038 -0.00222
C14 1 0.393786 0.477621 0.289438 11.00000 0.03126 0.07244 =
0.04405 0.00783 -0.01827 -0.00593
AFIX 43
H14 2 0.432071 0.455284 0.316257 11.00000 -1.20000
AFIX 0
C12 1 0.392685 0.581041 0.178001 11.00000 0.04004 0.07305 =
0.04192 0.01394 -0.01584 -0.00948
H12 2 0.427927 0.631089 0.128073 11.00000 -1.20000
C5 1 -0.050503 0.377265 0.159800 11.00000 0.04535 0.05352 =
0.05171 -0.00026 -0.02203 -0.00192
H5 2 0.023325 0.341006 0.140963 11.00000 -1.20000
C21 1 0.210717 0.674089 0.513887 11.00000 0.05635 0.05570 =
0.04379 0.00032 -0.02263 0.01190
H21 2 0.141395 0.636626 0.524603 11.00000 -1.20000
C13 1 0.447148 0.546504 0.219039 11.00000 0.02991 0.08033 =
0.04789 0.01184 -0.01433 -0.01079
H13 2 0.521548 0.574150 0.196896 11.00000 -1.20000
C2 1 -0.263398 0.487629 0.217467 11.00000 0.04802 0.07299 =
0.06845 0.01092 -0.03647 0.00257
AFIX 43
H2 2 -0.335387 0.525035 0.237136 11.00000 -1.20000
AFIX 0
C4 1 -0.103703 0.374784 0.116599 11.00000 0.07292 0.06839 =
0.05243 -0.00366 -0.03529 -0.00340
AFIX 43
H4 2 -0.067625 0.335819 0.067806 11.00000 -1.20000
AFIX 0
C20 1 0.235197 0.841049 0.531326 11.00000 0.12122 0.05527 =
0.05800 -0.00925 -0.04878 0.02776
AFIX 43
H20 2 0.179650 0.922169 0.555714 11.00000 -1.20000
AFIX 0
C17 1 0.401583 0.604049 0.459065 11.00000 0.04594 0.07468 =
0.05445 0.00240 -0.02012 -0.01230
AFIX 43
H17 2 0.458003 0.524473 0.434484 11.00000 -1.20000
AFIX 0
C18 1 0.422915 0.768859 0.477734 11.00000 0.08755 0.08702 =
0.07797 0.01081 -0.04148 -0.04058
AFIX 43
H18 2 0.493976 0.800228 0.466374 11.00000 -1.20000
AFIX 0
C19 1 0.340864 0.885675 0.512595 11.00000 0.13838 0.05655 =
0.07750 0.01369 -0.06553 -0.02991
AFIX 43
H19 2 0.356449 0.997593 0.523961 11.00000 -1.20000
AFIX 0
C3 1 -0.210308 0.429919 0.145503 11.00000 0.07890 0.07732 =
0.07077 0.00510 -0.05520 -0.00208
AFIX 43
H3 2 -0.246279 0.428048 0.116293 11.00000 -1.20000
AFIX 0
C7 1 -0.045400 0.438156 0.279418 11.00000 0.03568 0.05116 =
0.04620 0.00556 -0.01993 -0.00275
AFIX 43
H7 2 -0.088486 0.451380 0.330177 11.00000 -1.20000
AFIX 0
HKLF 4
REM new in P21/c #14
REM R1 = 0.0384 for 3394 Fo > 4sig(Fo) and 0.0447 for all 3880 data
REM 259 parameters refined using 0 restraints
END
WGHT 0.0527 0.6427
REM Highest difference peak 0.265, deepest hole -0.331, 1-sigma level 0.044
Q1 1 -0.2453 0.5514 0.2985 11.00000 0.05 0.27
Q2 1 0.1684 0.4641 0.2952 11.00000 0.05 0.26
Q3 1 0.2263 0.3315 0.5067 11.00000 0.05 0.24
Q4 1 -0.1452 0.4907 0.2419 11.00000 0.05 0.23
Q5 1 0.2569 0.4213 0.2928 11.00000 0.05 0.22
Q6 1 0.2584 0.3470 0.4112 11.00000 0.05 0.22
Q7 1 -0.0697 0.4389 0.2511 11.00000 0.05 0.22
Q8 1 -0.0788 0.3925 0.2040 11.00000 0.05 0.22
Q9 1 -0.2904 0.4623 0.3593 11.00000 0.05 0.22
Q10 1 -0.2241 0.6073 0.3522 11.00000 0.05 0.21
Q11 1 0.2472 0.4684 0.2999 11.00000 0.05 0.21
Q12 1 0.3426 0.4288 0.3010 11.00000 0.05 0.21
Q13 1 0.0811 0.4184 0.2805 11.00000 0.05 0.21
Q14 1 0.3323 0.4726 0.3093 11.00000 0.05 0.21
Q15 1 0.4095 0.3194 0.4098 11.00000 0.05 0.20
Q16 1 0.3436 0.5816 0.4605 11.00000 0.05 0.19
Q17 1 -0.0677 0.4200 0.1320 11.00000 0.05 0.19
Q18 1 0.2591 0.4102 0.3622 11.00000 0.05 0.19
Q19 1 0.2825 0.4742 0.4686 11.00000 0.05 0.19
Q20 1 -0.2312 0.4939 0.1714 11.00000 0.05 0.18
;
_shelx_res_checksum 48657
_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 > 2\s(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/[\s^2^(Fo^2^)+(0.0495P)^2^+4.5555P] where P=(Fo^2^+2Fc^2^)/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 . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0418(3) 0.0511(4) 0.0326(3) 0.0013(3) 0.0126(2) 0.0031(3)
C10 0.0330(11) 0.0395(12) 0.0338(12) -0.0003(9) 0.0124(9) 0.0001(9)
N1 0.0349(10) 0.0729(15) 0.0337(11) 0.0101(10) 0.0139(8) 0.0054(10)
F1 0.0657(10) 0.0962(13) 0.0758(12) 0.0227(10) 0.0443(9) 0.0130(9)
O3 0.0544(10) 0.0503(11) 0.0526(11) 0.0051(9) 0.0164(8) -0.0047(8)
C16 0.0325(11) 0.0480(13) 0.0307(11) 0.0022(10) 0.0055(9) -0.0019(9)
C8 0.0360(12) 0.0555(15) 0.0408(14) 0.0035(12) 0.0144(10) 0.0052(11)
C15 0.0366(11) 0.0425(13) 0.0329(12) 0.0016(10) 0.0133(9) 0.0042(9)
O1 0.0477(10) 0.1118(17) 0.0467(11) 0.0252(11) 0.0260(9) 0.0226(10)
C6 0.0344(12) 0.0420(13) 0.0470(14) -0.0066(11) 0.0156(10) -0.0006(10)
C11 0.0359(12) 0.0641(17) 0.0336(12) 0.0008(11) 0.0096(10) 0.0039(11)
C14 0.0348(12) 0.0747(18) 0.0395(14) -0.0005(13) 0.0128(10) 0.0102(12)
O2 0.0650(11) 0.0759(13) 0.0360(10) -0.0041(9) 0.0228(8) 0.0110(10)
C9 0.0366(12) 0.0510(14) 0.0391(13) 0.0031(11) 0.0154(10) 0.0025(10)
C7 0.0390(12) 0.0502(14) 0.0421(13) 0.0033(11) 0.0151(10) 0.0019(10)
C17 0.0367(12) 0.0604(16) 0.0430(14) 0.0069(12) 0.0133(10) -0.0006(11)
C21 0.0478(14) 0.0577(16) 0.0345(13) 0.0015(11) 0.0161(10) -0.0037(12)
C5 0.0427(13) 0.0592(16) 0.0458(14) -0.0041(12) 0.0170(11) 0.0041(12)
C13 0.0417(13) 0.083(2) 0.0420(14) -0.0062(14) 0.0224(11) 0.0051(13)
C2 0.0382(14) 0.073(2) 0.077(2) -0.0125(16) 0.0243(13) 0.0052(13)
C4 0.0554(16) 0.074(2) 0.0452(15) -0.0008(14) 0.0064(12) 0.0126(14)
C12 0.0463(14) 0.0803(19) 0.0309(13) -0.0034(13) 0.0161(10) 0.0019(13)
C1 0.0439(13) 0.0536(15) 0.0537(15) -0.0004(13) 0.0221(11) -0.0004(11)
C18 0.0428(14) 0.0691(18) 0.0523(16) 0.0054(14) 0.0166(12) 0.0100(13)
C19 0.0600(16) 0.0543(16) 0.0462(15) 0.0032(13) 0.0089(12) 0.0111(13)
C3 0.0406(15) 0.085(2) 0.064(2) -0.0119(17) 0.0053(13) 0.0171(15)
C20 0.0665(18) 0.0518(16) 0.0425(15) 0.0074(12) 0.0167(13) -0.0024(13)
_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
_shelx_res_file
;
TITL mo_G35_0m in C2/c
shelx.res
created by SHELXL-2016/6 at 21:05:50 on 16-May-2018
CELL 0.71073 26.9841 7.6486 18.3543 90.000 107.479 90.000
ZERR 8.00 0.0027 0.0008 0.0020 0.000 0.003 0.000
LATT 7
SYMM - X, Y, 1/2 - Z
SFAC C H N O F S
UNIT 168 128 8 24 8 8
MERG 2
OMIT -3.00 150.00
EQIV $1 -1/2+x,3/2-y,-1/2+z
EQIV $2 1/2-x,3/2-y,-z
EQIV $3 1/2-x,-1/2+y,1/2-z
HTAB C3 O2_$1
HTAB C5 O3_$2
HTAB C8 O3_$2
HTAB C20 O1_$3
FMAP 2
PLAN 20
SIZE 0.079 0.098 0.104
ACTA
BOND
L.S. 4
TEMP 23.00
WGHT 0.049500 4.555501
FVAR 0.07051
MOLE 1
S1 6 0.333403 0.498996 0.195742 11.00000 0.04178 0.05111 =
0.03261 0.00134 0.01265 0.00309
C10 1 0.220626 0.522637 0.001616 11.00000 0.03300 0.03953 =
0.03384 -0.00026 0.01244 0.00011
N1 3 0.279977 0.464770 0.127709 11.00000 0.03488 0.07291 =
0.03370 0.01014 0.01395 0.00539
AFIX 43
H1 2 0.253675 0.433821 0.141955 11.00000 -1.20000
AFIX 0
F1 5 0.004525 0.666593 0.069368 11.00000 0.06568 0.09617 =
0.07580 0.02272 0.04430 0.01296
O3 4 0.364896 0.620454 0.170080 11.00000 0.05444 0.05026 =
0.05263 0.00508 0.01640 -0.00467
C16 1 0.367467 0.298829 0.212903 11.00000 0.03253 0.04796 =
0.03072 0.00218 0.00552 -0.00193
C8 1 0.128775 0.633751 -0.013889 11.00000 0.03601 0.05546 =
0.04084 0.00352 0.01444 0.00516
H8 2 0.129503 0.677754 -0.062411 11.00000 -1.20000
C15 1 0.270991 0.479067 0.048365 11.00000 0.03663 0.04254 =
0.03292 0.00162 0.01328 0.00416
O1 4 0.179892 0.502036 0.099032 11.00000 0.04769 0.11177 =
0.04667 0.02517 0.02596 0.02256
C6 1 0.038773 0.735921 -0.030743 11.00000 0.03441 0.04197 =
0.04703 -0.00662 0.01558 -0.00064
C11 1 0.212772 0.538025 -0.076924 11.00000 0.03591 0.06406 =
0.03361 0.00079 0.00957 0.00394
AFIX 43
H11 2 0.179862 0.566712 -0.108624 11.00000 -1.20000
AFIX 0
C14 1 0.310275 0.452769 0.015551 11.00000 0.03482 0.07466 =
0.03950 -0.00050 0.01278 0.01015
AFIX 43
H14 2 0.343427 0.423715 0.046301 11.00000 -1.20000
AFIX 0
O2 4 0.317149 0.538040 0.261433 11.00000 0.06500 0.07585 =
0.03602 -0.00414 0.02278 0.01102
C9 1 0.176735 0.549093 0.033593 11.00000 0.03663 0.05098 =
0.03908 0.00308 0.01538 0.00246
C7 1 0.087664 0.651609 0.010589 11.00000 0.03895 0.05017 =
0.04207 0.00329 0.01507 0.00188
AFIX 43
H7 2 0.090146 0.606247 0.058567 11.00000 -1.20000
AFIX 0
C17 1 0.407811 0.268772 0.182117 11.00000 0.03674 0.06039 =
0.04300 0.00690 0.01327 -0.00065
AFIX 43
H17 2 0.417093 0.353991 0.152498 11.00000 -1.20000
AFIX 0
C21 1 0.354093 0.173378 0.258038 11.00000 0.04780 0.05769 =
0.03446 0.00154 0.01606 -0.00370
AFIX 43
H21 2 0.327256 0.193892 0.279020 11.00000 -1.20000
AFIX 0
C5 1 0.029798 0.816689 -0.101838 11.00000 0.04265 0.05915 =
0.04578 -0.00405 0.01703 0.00408
H5 2 0.057321 0.820278 -0.125817 11.00000 -1.20000
C13 1 0.300857 0.469158 -0.062494 11.00000 0.04169 0.08296 =
0.04203 -0.00622 0.02240 0.00510
AFIX 43
H13 2 0.327695 0.450963 -0.083710 11.00000 -1.20000
AFIX 0
C2 1 -0.049619 0.814839 -0.036067 11.00000 0.03817 0.07274 =
0.07669 -0.01252 0.02433 0.00523
AFIX 43
H2 2 -0.076190 0.812850 -0.013473 11.00000 -1.20000
AFIX 0
C4 1 -0.017007 0.894723 -0.138659 11.00000 0.05539 0.07420 =
0.04520 -0.00077 0.00639 0.01258
AFIX 43
H4 2 -0.021781 0.948888 -0.185635 11.00000 -1.20000
AFIX 0
C12 1 0.252365 0.511930 -0.108720 11.00000 0.04632 0.08029 =
0.03087 -0.00342 0.01608 0.00194
AFIX 43
H12 2 0.246200 0.523277 -0.161144 11.00000 -1.20000
AFIX 0
C1 1 -0.002545 0.740396 -0.000461 11.00000 0.04388 0.05360 =
0.05370 -0.00039 0.02206 -0.00043
C18 1 0.434025 0.111627 0.195776 11.00000 0.04284 0.06910 =
0.05225 0.00542 0.01656 0.01001
AFIX 43
H18 2 0.460756 0.089842 0.174720 11.00000 -1.20000
AFIX 0
C19 1 0.420675 -0.012427 0.240386 11.00000 0.05999 0.05432 =
0.04618 0.00315 0.00892 0.01109
AFIX 43
H19 2 0.438570 -0.118002 0.249729 11.00000 -1.20000
AFIX 0
C3 1 -0.056880 0.892661 -0.105914 11.00000 0.04062 0.08490 =
0.06450 -0.01187 0.00529 0.01712
H3 2 -0.089976 0.940610 -0.131200 11.00000 -1.20000
C20 1 0.380989 0.018043 0.271461 11.00000 0.06653 0.05177 =
0.04254 0.00743 0.01671 -0.00244
H20 2 0.372188 -0.067084 0.297439 11.00000 -1.20000
HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00
REM mo_G35_0m in C2/c
REM R1 = 0.0453 for 2712 Fo > 4sig(Fo) and 0.0706 for all 3749 data
REM 256 parameters refined using 0 restraints
END
WGHT 0.0503 4.5167
REM Highest difference peak 0.295, deepest hole -0.313, 1-sigma level 0.047
Q1 1 0.2524 0.5119 0.1414 11.00000 0.05 0.29
Q2 1 0.3584 0.3970 0.2112 11.00000 0.05 0.25
Q3 1 0.1994 0.5091 0.0155 11.00000 0.05 0.20
Q4 1 0.2442 0.5320 0.0211 11.00000 0.05 0.20
Q5 1 0.1898 0.6130 0.0978 11.00000 0.05 0.19
Q6 1 0.1488 0.5381 0.0018 11.00000 0.05 0.18
Q7 1 0.0778 0.4943 0.0401 11.00000 0.05 0.18
Q8 1 0.3007 0.4444 0.1583 11.00000 0.05 0.17
Q9 1 0.1114 0.7982 0.0726 11.00000 0.05 0.16
Q10 1 0.3447 0.5080 0.0400 11.00000 0.05 0.16
Q11 1 0.4336 0.2264 0.2139 11.00000 0.05 0.16
Q12 1 0.0667 0.7452 0.0031 11.00000 0.05 0.16
Q13 1 0.2289 0.4600 -0.0916 11.00000 0.05 0.15
Q14 1 0.3908 0.3070 0.2120 11.00000 0.05 0.15
Q15 1 0.0222 0.7803 0.0819 11.00000 0.05 0.15
Q16 1 0.1025 0.5370 -0.0104 11.00000 0.05 0.15
Q17 1 0.3385 0.6332 0.1827 11.00000 0.05 0.15
Q18 1 0.3521 0.2173 0.2161 11.00000 0.05 0.14
Q19 1 0.2020 0.6033 0.0195 11.00000 0.05 0.14
Q20 1 0.3629 -0.1956 0.2607 11.00000 0.05 0.14
;
_shelx_res_checksum 30300
#######################################################################
#
# 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 \l/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 '\f and \w 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0551P)^2^+1.1934P] where P=(Fo^2^+2Fc^2^)/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 . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0295(3) 0.0438(4) 0.0497(3) -0.0004(2) 0.0101(2) -0.0050(2)
O1 0.0405(9) 0.0369(9) 0.0819(13) 0.0000(8) 0.0227(9) 0.0043(7)
O4 0.0416(9) 0.0383(9) 0.0818(13) -0.0011(8) 0.0240(9) 0.0030(8)
O3 0.0568(11) 0.0501(11) 0.0670(12) -0.0079(9) 0.0178(9) -0.0246(9)
O2 0.0285(8) 0.0738(13) 0.0694(12) 0.0059(10) 0.0103(8) 0.0110(8)
N1 0.0322(9) 0.0386(10) 0.0482(11) 0.0048(8) 0.0116(8) 0.0015(8)
C11 0.0334(11) 0.0365(12) 0.0360(11) 0.0016(9) 0.0094(8) 0.0021(9)
C17 0.0303(11) 0.0376(12) 0.0448(12) 0.0001(9) 0.0137(9) 0.0007(9)
C12 0.0351(11) 0.0375(12) 0.0348(11) 0.0005(9) 0.0081(9) 0.0007(9)
C10 0.0400(12) 0.0368(12) 0.0382(11) 0.0020(9) 0.0148(9) 0.0020(10)
C9 0.0374(11) 0.0375(13) 0.0462(12) 0.0051(10) 0.0131(9) -0.0008(10)
C1 0.0417(12) 0.0345(12) 0.0386(11) 0.0012(9) 0.0110(9) -0.0002(10)
C6 0.0400(12) 0.0372(12) 0.0398(11) 0.0000(9) 0.0113(9) -0.0021(10)
C8 0.0394(12) 0.0422(13) 0.0456(12) 0.0006(10) 0.0168(10) 0.0000(10)
C16 0.0385(12) 0.0428(14) 0.0627(15) -0.0037(11) 0.0183(11) 0.0024(11)
C2 0.0445(13) 0.0499(15) 0.0475(13) -0.0014(11) 0.0127(11) -0.0095(11)
C22 0.0453(14) 0.0388(14) 0.0621(16) 0.0081(11) 0.0138(11) 0.0010(11)
C18 0.0583(16) 0.0358(13) 0.0546(14) 0.0001(11) 0.0083(12) 0.0001(12)
C13 0.0469(14) 0.0399(13) 0.0622(16) -0.0030(11) 0.0162(12) -0.0034(11)
C5 0.0488(14) 0.0420(14) 0.0580(15) -0.0052(11) 0.0158(11) 0.0029(12)
C21 0.0533(16) 0.0660(18) 0.0602(17) 0.0197(14) 0.0118(13) 0.0144(14)
C4 0.0654(17) 0.0337(13) 0.0650(16) -0.0081(11) 0.0105(13) 0.0004(12)
C3 0.0590(16) 0.0420(14) 0.0534(15) -0.0012(11) 0.0087(12) -0.0156(13)
C20 0.0478(15) 0.076(2) 0.0544(16) -0.0062(14) 0.0019(12) 0.0051(14)
C19 0.0623(17) 0.0512(16) 0.0647(17) -0.0127(13) 0.0060(14) -0.0043(14)
C15 0.0485(15) 0.0475(15) 0.0817(19) -0.0084(13) 0.0252(13) 0.0096(13)
C14 0.0633(17) 0.0338(13) 0.0805(19) -0.0056(12) 0.0215(14) 0.0066(13)
C7 0.0433(15) 0.0576(18) 0.109(3) -0.0042(16) 0.0264(15) 0.0102(14)
_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
_iucr_refine_instructions_details
;
mo_g22_0m.res created by SHELXL-2014/7
TITL mo_g22_0m_a.res in P2(1)/n
REM Old TITL mo_G22_0m in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.155, Rweak 0.004, Alpha 0.028, Orientation as input
REM Formula found by SHELXT: C22 N O4 S
CELL 0.71073 11.6707 12.5558 13.3311 90 101.004 90
ZERR 4 0.0012 0.0013 0.0014 0 0.003 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 88 76 4 16 4
EQIV $1 0.5-X,-0.5+Y,0.5-Z
EQIV $2 1+X,+Y,+Z
EQIV $3 0.5-X,0.5+Y,0.5-Z
L.S. 5
PLAN -31 0 0
SIZE 0.254 0.295 0.309
TEMP 23
HTAB N1 O1
HTAB C22 O1_$1
HTAB C7 O2_$2
HTAB C18 O3_$3
HTAB C5 O2_$3
HTAB
list 4
fmap 2
acta
REM
REM
REM
WGHT 0.055100 1.193400
FVAR 0.34055
S1 5 0.182403 0.285056 0.201734 11.00000 0.02951 0.04385 =
0.04965 -0.00036 0.01005 -0.00496
O1 4 0.371346 0.502000 0.118569 11.00000 0.04052 0.03691 =
0.08190 -0.00001 0.02269 0.00426
O4 4 0.803486 0.585066 0.116387 11.00000 0.04157 0.03833 =
0.08182 -0.00106 0.02397 0.00295
O3 4 0.157966 0.174151 0.191753 11.00000 0.05683 0.05010 =
0.06700 -0.00785 0.01779 -0.02460
O2 4 0.088118 0.359399 0.183675 11.00000 0.02850 0.07376 =
0.06940 0.00592 0.01028 0.01101
N1 3 0.265906 0.320907 0.121950 11.00000 0.03224 0.03860 =
0.04816 0.00484 0.01164 0.00150
AFIX 3
H1 2 0.246166 0.394437 0.113720 11.00000 -1.20000
AFIX 0
C11 1 0.471024 0.338355 0.110252 11.00000 0.03343 0.03651 =
0.03599 0.00158 0.00944 0.00210
C17 1 0.264485 0.308227 0.325739 11.00000 0.03026 0.03765 =
0.04479 0.00006 0.01375 0.00067
C12 1 0.374117 0.273081 0.115728 11.00000 0.03511 0.03748 =
0.03479 0.00051 0.00815 0.00073
C10 1 0.465849 0.456385 0.118645 11.00000 0.04001 0.03678 =
0.03818 0.00197 0.01484 0.00204
C9 1 0.572913 0.520416 0.127598 11.00000 0.03737 0.03749 =
0.04618 0.00510 0.01310 -0.00081
AFIX 43
H9 2 0.641974 0.488133 0.118644 11.00000 -1.20000
AFIX 0
C1 1 0.776202 0.686983 0.135045 11.00000 0.04173 0.03448 =
0.03858 0.00115 0.01100 -0.00022
C6 1 0.662457 0.704826 0.154434 11.00000 0.04005 0.03721 =
0.03981 -0.00001 0.01128 -0.00209
C8 1 0.571947 0.624179 0.148402 11.00000 0.03935 0.04216 =
0.04563 0.00062 0.01678 0.00004
AFIX 43
H8 2 0.501221 0.649364 0.161281 11.00000 -1.20000
AFIX 0
C16 1 0.573434 0.287200 0.095179 11.00000 0.03845 0.04276 =
0.06267 -0.00367 0.01832 0.00242
AFIX 43
H16 2 0.638105 0.328411 0.089509 11.00000 -1.20000
AFIX 0
C2 1 0.852207 0.771775 0.134701 11.00000 0.04450 0.04989 =
0.04752 -0.00136 0.01268 -0.00955
AFIX 43
H2 2 0.925824 0.759968 0.119786 11.00000 -1.20000
AFIX 0
C22 1 0.290943 0.226296 0.394631 11.00000 0.04531 0.03875 =
0.06206 0.00808 0.01381 0.00099
AFIX 43
H22 2 0.267145 0.157027 0.376792 11.00000 -1.20000
AFIX 0
C18 1 0.300264 0.411348 0.351587 11.00000 0.05832 0.03576 =
0.05456 0.00009 0.00827 0.00013
AFIX 43
H18 2 0.282372 0.466098 0.304199 11.00000 -1.20000
AFIX 0
C13 1 0.383052 0.163279 0.109111 11.00000 0.04686 0.03987 =
0.06225 -0.00304 0.01616 -0.00337
AFIX 43
H13 2 0.318711 0.120743 0.112662 11.00000 -1.20000
AFIX 0
C5 1 0.634322 0.809002 0.176925 11.00000 0.04877 0.04202 =
0.05796 -0.00517 0.01582 0.00290
AFIX 43
H5 2 0.560697 0.822653 0.191048 11.00000 -1.20000
AFIX 0
C21 1 0.354060 0.249260 0.491562 11.00000 0.05330 0.06599 =
0.06023 0.01969 0.01175 0.01442
AFIX 43
H21 2 0.372186 0.194909 0.539353 11.00000 -1.20000
AFIX 0
C4 1 0.711285 0.892300 0.179013 11.00000 0.06536 0.03369 =
0.06498 -0.00809 0.01045 0.00044
AFIX 43
H4 2 0.690435 0.960642 0.195592 11.00000 -1.20000
AFIX 0
C3 1 0.819627 0.873103 0.156220 11.00000 0.05901 0.04200 =
0.05341 -0.00116 0.00866 -0.01555
AFIX 43
H3 2 0.871301 0.929337 0.155384 11.00000 -1.20000
AFIX 0
C20 1 0.389788 0.351188 0.517311 11.00000 0.04779 0.07561 =
0.05444 -0.00616 0.00186 0.00508
AFIX 43
H20 2 0.432740 0.365518 0.582126 11.00000 -1.20000
AFIX 0
C19 1 0.362506 0.432137 0.447966 11.00000 0.06228 0.05116 =
0.06470 -0.01265 0.00602 -0.00429
AFIX 43
H19 2 0.386159 0.501366 0.466137 11.00000 -1.20000
AFIX 0
C15 1 0.581249 0.178884 0.088564 11.00000 0.04848 0.04749 =
0.08167 -0.00835 0.02522 0.00956
AFIX 43
H15 2 0.650107 0.147248 0.078222 11.00000 -1.20000
AFIX 0
C14 1 0.486084 0.116970 0.097369 11.00000 0.06331 0.03383 =
0.08052 -0.00562 0.02147 0.00663
AFIX 43
H14 2 0.491829 0.043156 0.095326 11.00000 -1.20000
AFIX 0
C7 1 0.918502 0.563321 0.099923 11.00000 0.04334 0.05764 =
0.10929 -0.00422 0.02642 0.01024
AFIX 137
H7A 2 0.930991 0.600139 0.039816 11.00000 -1.50000
H7B 2 0.927301 0.488092 0.090986 11.00000 -1.50000
H7C 2 0.974576 0.587105 0.157892 11.00000 -1.50000
AFIX 0
HKLF 4
REM mo_g22_0m_a.res in P2(1)/n
REM R1 = 0.0504 for 3122 Fo > 4sig(Fo) and 0.0712 for all 3952 data
REM 254 parameters refined using 0 restraints
END
WGHT 0.0551 1.1934
REM Instructions for potential hydrogen bonds
HTAB N1 O1
HTAB C9 O4
HTAB C22 O1_$1
HTAB C13 O3
HTAB C7 O2_$2
REM Highest difference peak 0.514, deepest hole -0.428, 1-sigma level 0.051
Q1 1 0.2273 0.2984 0.2687 11.00000 0.05 0.51
Q2 1 0.1993 0.2987 0.1388 11.00000 0.05 0.31
Q3 1 0.4669 0.3948 0.1112 11.00000 0.05 0.27
Q4 1 0.1831 0.2166 0.2341 11.00000 0.05 0.27
Q5 1 0.1600 0.2185 0.1372 11.00000 0.05 0.26
Q6 1 0.1720 0.3460 0.2404 11.00000 0.05 0.26
Q7 1 0.2790 0.3371 0.2003 11.00000 0.05 0.24
Q8 1 0.2967 0.4012 0.1375 11.00000 0.05 0.24
Q9 1 0.1046 0.4010 0.2425 11.00000 0.05 0.23
Q10 1 0.6564 0.7510 0.2012 11.00000 0.05 0.22
Q11 1 0.2629 0.2735 0.3526 11.00000 0.05 0.22
Q12 1 0.8408 0.8131 0.1854 11.00000 0.05 0.21
Q13 1 0.1561 0.1532 0.1277 11.00000 0.05 0.21
Q14 1 0.3022 0.4333 0.4088 11.00000 0.05 0.20
Q15 1 0.8971 0.5052 0.0453 11.00000 0.05 0.19
Q16 1 0.1598 0.1445 0.2060 11.00000 0.05 0.19
Q17 1 0.3823 0.2211 0.1446 11.00000 0.05 0.19
Q18 1 0.7984 0.5579 0.1802 11.00000 0.05 0.18
Q19 1 0.5747 0.5794 0.1017 11.00000 0.05 0.18
Q20 1 0.7996 0.7364 0.1121 11.00000 0.05 0.18
Q21 1 0.3569 0.2187 0.4475 11.00000 0.05 0.18
Q22 1 0.8295 0.7212 0.1765 11.00000 0.05 0.17
Q23 1 0.5630 0.2353 0.0459 11.00000 0.05 0.17
Q24 1 0.5819 0.2344 0.1280 11.00000 0.05 0.17
Q25 1 0.3681 0.3761 0.4669 11.00000 0.05 0.17
Q26 1 0.4018 0.2756 0.4811 11.00000 0.05 0.17
Q27 1 0.2936 0.1727 0.3636 11.00000 0.05 0.17
Q28 1 0.2926 0.3441 0.3208 11.00000 0.05 0.17
Q29 1 0.5140 0.3160 0.1152 11.00000 0.05 0.16
Q30 1 0.2357 0.3142 0.3320 11.00000 0.05 0.16
Q31 1 0.2200 0.1656 0.2683 11.00000 0.05 0.16
REM The information below was added by Olex2.
REM
REM R1 = 0.0504 for 3122 Fo > 4sig(Fo) and 0.0712 for all 25272 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.51, deepest hole -0.43
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0712
REM R1_gt = 0.0504
REM wR_ref = 0.1389
REM GOOF = 1.119
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 25272
REM Reflections_gt = 3122
REM Parameters = n/a
REM Hole = -0.43
REM Peak = 0.51
REM Flack = n/a
;
_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 > 2\s(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/[\s^2^(Fo^2^)+(0.0486P)^2^+0.5715P] where P=(Fo^2^+2Fc^2^)/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+0.001xFc^2^\l^3^/sin(2\q)]^-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 . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0542(3) 0.0443(3) 0.0565(3) 0.00677(18) 0.0174(2) -0.00227(19)
C16 0.0475(9) 0.0384(8) 0.0566(10) 0.0009(7) 0.0215(8) -0.0044(7)
N1 0.0460(9) 0.0439(8) 0.0749(11) 0.0048(7) 0.0123(8) 0.0011(7)
O2 0.0688(9) 0.0444(7) 0.0804(9) 0.0134(6) 0.0120(7) 0.0032(6)
O3 0.0807(10) 0.0719(9) 0.0580(8) 0.0034(6) 0.0333(7) -0.0084(7)
O1 0.0656(9) 0.0463(8) 0.1433(15) 0.0175(8) 0.0490(10) 0.0100(6)
C6 0.0482(10) 0.0522(10) 0.0483(9) 0.0034(7) 0.0098(8) 0.0009(8)
C21 0.0555(10) 0.0463(9) 0.0633(11) 0.0026(8) 0.0240(9) 0.0037(8)
F1 0.0880(10) 0.1164(12) 0.1171(12) -0.0032(9) 0.0550(9) -0.0336(9)
C15 0.0478(9) 0.0433(9) 0.0449(9) -0.0007(7) 0.0063(7) 0.0021(7)
C8 0.0526(10) 0.0447(9) 0.0605(11) 0.0045(8) 0.0136(9) 0.0012(8)
C9 0.0507(10) 0.0458(10) 0.0579(10) 0.0045(8) 0.0122(8) 0.0017(8)
C10 0.0490(9) 0.0422(9) 0.0449(9) 0.0000(7) 0.0091(7) 0.0021(7)
C4 0.0649(13) 0.0578(11) 0.0710(13) 0.0063(9) 0.0128(10) -0.0105(10)
C5 0.0496(11) 0.0536(11) 0.0633(11) 0.0042(9) 0.0091(9) 0.0008(8)
C7 0.0558(11) 0.0462(10) 0.0631(11) 0.0047(8) 0.0159(9) 0.0016(8)
C14 0.0552(11) 0.0575(11) 0.0692(12) -0.0009(9) 0.0224(9) 0.0046(9)
C17 0.0517(11) 0.0637(12) 0.0731(13) -0.0121(10) 0.0203(10) 0.0035(9)
C1 0.0659(13) 0.0566(12) 0.0812(14) 0.0013(10) 0.0288(11) 0.0062(10)
C19 0.0891(17) 0.0540(12) 0.0660(13) -0.0045(10) -0.0012(12) 0.0067(11)
C3 0.0606(13) 0.0832(15) 0.0629(12) -0.0013(10) 0.0245(10) -0.0185(11)
C11 0.0690(13) 0.0444(10) 0.0734(13) 0.0030(9) 0.0269(10) 0.0046(9)
C20 0.0873(16) 0.0492(10) 0.0585(12) -0.0008(9) 0.0253(11) 0.0016(10)
C12 0.0881(16) 0.0459(11) 0.0965(16) 0.0038(10) 0.0395(14) 0.0160(11)
C13 0.0712(14) 0.0619(13) 0.0880(15) -0.0002(11) 0.0348(12) 0.0200(11)
C18 0.0563(12) 0.0681(14) 0.0913(16) -0.0116(12) 0.0001(11) 0.0126(10)
C2 0.0648(13) 0.0833(16) 0.0882(16) -0.0057(12) 0.0369(12) 0.0026(12)
_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
_shelx_res_file
;
TITL
shelx.res
created by SHELXL-2016/6 at 15:56:02 on 11-Jun-2018
CELL 0.71073 13.1059 17.5044 8.1948 90.000 102.278 90.000
ZERR 4.00 0.0005 0.0008 0.0004 0.000 0.002 0.000
LATT 1
SYMM - X, 1/2 + Y, 1/2 - Z
SFAC C H O F S N
UNIT 84 64 12 4 4 4
MERG 2
OMIT -3.00 150.00
EQIV $1 1-x,-y,-z
EQIV $2 1-x,1/2+y,1/2-z
EQIV $3 x,y,-1+z
EQIV $4 -1+x,1/2-y,-1/2+z
HTAB C20 O1_$1
HTAB C5 O2_$2
HTAB C20 O3_$3
HTAB C19 F1_$4
FMAP 2
PLAN 20
SIZE 0.213 0.223 0.647
ACTA
BOND
CONF
L.S. 4
TEMP 23.00
WGHT 0.048600 0.571500
EXTI 0.028490
FVAR 0.14526
MOLE 1
S1 5 0.332655 0.022775 0.329502 11.00000 0.05417 0.04425 =
0.05651 0.00677 0.01741 -0.00227
C16 1 0.252332 0.024425 0.127785 11.00000 0.04751 0.03845 =
0.05661 0.00093 0.02151 -0.00444
N1 6 0.414719 0.092556 0.334629 11.00000 0.04602 0.04395 =
0.07494 0.00482 0.01231 0.00112
O2 3 0.395414 -0.044507 0.344704 11.00000 0.06882 0.04442 =
0.08044 0.01338 0.01204 0.00317
O3 3 0.267040 0.036240 0.445040 11.00000 0.08069 0.07193 =
0.05799 0.00336 0.03333 -0.00836
O1 3 0.587077 0.119825 0.240316 11.00000 0.06561 0.04629 =
0.14331 0.01753 0.04905 0.00998
C6 1 0.815258 0.257522 0.097030 11.00000 0.04819 0.05215 =
0.04829 0.00340 0.00976 0.00090
C21 1 0.291050 -0.004759 -0.004256 11.00000 0.05554 0.04631 =
0.06332 0.00258 0.02402 0.00366
AFIX 43
H21 2 0.357772 -0.025652 0.014450 11.00000 -1.20000
AFIX 0
F1 4 1.054837 0.371905 -0.047852 11.00000 0.08798 0.11641 =
0.11710 -0.00323 0.05503 -0.03362
C15 1 0.392907 0.171233 0.312227 11.00000 0.04784 0.04330 =
0.04487 -0.00071 0.00633 0.00212
C8 1 0.642406 0.240650 0.176484 11.00000 0.05258 0.04471 =
0.06046 0.00448 0.01356 0.00119
AFIX 43
H8 2 0.627751 0.292625 0.166066 11.00000 -1.20000
AFIX 0
C9 1 0.566488 0.188633 0.227778 11.00000 0.05065 0.04578 =
0.05793 0.00448 0.01224 0.00168
C10 1 0.468318 0.219176 0.264113 11.00000 0.04900 0.04224 =
0.04487 0.00002 0.00913 0.00212
C4 1 0.894569 0.375242 0.034995 11.00000 0.06489 0.05776 =
0.07105 0.00630 0.01284 -0.01050
AFIX 43
H4 2 0.893568 0.428197 0.025587 11.00000 -1.20000
AFIX 0
C5 1 0.813576 0.336675 0.082030 11.00000 0.04965 0.05362 =
0.06332 0.00418 0.00909 0.00080
C7 1 0.730655 0.214743 0.145160 11.00000 0.05583 0.04620 =
0.06314 0.00465 0.01594 0.00155
C14 1 0.301063 0.202514 0.341404 11.00000 0.05522 0.05746 =
0.06918 -0.00092 0.02237 0.00460
AFIX 43
H14 2 0.251656 0.171106 0.373762 11.00000 -1.20000
AFIX 0
C17 1 0.152798 0.055124 0.100519 11.00000 0.05165 0.06365 =
0.07307 -0.01208 0.02031 0.00355
AFIX 43
H17 2 0.126476 0.074284 0.189099 11.00000 -1.20000
AFIX 0
C1 1 0.900881 0.218396 0.064720 11.00000 0.06585 0.05662 =
0.08119 0.00135 0.02879 0.00619
AFIX 43
H1A 2 0.903430 0.165482 0.074987 11.00000 -1.20000
AFIX 0
C19 1 0.131963 0.028024 -0.190933 11.00000 0.08910 0.05405 =
0.06597 -0.00447 -0.00123 0.00671
C3 1 0.976445 0.333573 0.002528 11.00000 0.06055 0.08320 =
0.06288 -0.00130 0.02453 -0.01847
C11 1 0.446523 0.297528 0.249219 11.00000 0.06902 0.04439 =
0.07340 0.00304 0.02689 0.00456
AFIX 43
H11 2 0.495537 0.330133 0.219393 11.00000 -1.20000
AFIX 0
C20 1 0.230065 -0.002588 -0.163127 11.00000 0.08730 0.04921 =
0.05854 -0.00081 0.02529 0.00165
C12 1 0.355214 0.327649 0.277229 11.00000 0.08805 0.04588 =
0.09651 0.00379 0.03948 0.01601
C13 1 0.282712 0.280131 0.322582 11.00000 0.07119 0.06191 =
0.08802 -0.00016 0.03485 0.02004
AFIX 43
H13 2 0.220495 0.300373 0.340876 11.00000 -1.20000
AFIX 0
C18 1 0.092995 0.056894 -0.060543 11.00000 0.05629 0.06813 =
0.09135 -0.01160 0.00012 0.01257
AFIX 43
H18 2 0.026194 0.077698 -0.080595 11.00000 -1.20000
AFIX 0
C2 1 0.982488 0.256387 0.017591 11.00000 0.06482 0.08333 =
0.08820 -0.00570 0.03694 0.00264
AFIX 43
H2 2 1.039864 0.229837 -0.003191 11.00000 -1.20000
AFIX 0
H1 2 0.470412 0.080232 0.316054 11.00000 -1.20000
H5 2 0.756399 0.364510 0.096571 11.00000 -1.20000
H7 2 0.741704 0.159689 0.154273 11.00000 -1.20000
H19 2 0.091964 0.028808 -0.299467 11.00000 -1.20000
H20 2 0.258814 -0.021455 -0.250982 11.00000 -1.20000
H12 2 0.343073 0.382728 0.264770 11.00000 -1.20000
HKLF 4
REM
REM R1 = 0.0395 for 2982 Fo > 4sig(Fo) and 0.0533 for all 3762 data
REM 263 parameters refined using 0 restraints
END
WGHT 0.0486 0.5777
REM Highest difference peak 0.315, deepest hole -0.278, 1-sigma level 0.046
Q1 1 0.2860 0.0260 0.2163 11.00000 0.05 0.31
Q2 1 0.2133 0.0218 0.1289 11.00000 0.05 0.21
Q3 1 0.2588 0.0037 0.0813 11.00000 0.05 0.20
Q4 1 0.5566 0.1343 0.1402 11.00000 0.05 0.18
Q5 1 0.3240 0.0260 0.4637 11.00000 0.05 0.17
Q6 1 0.4519 0.2004 0.3498 11.00000 0.05 0.17
Q7 1 0.3872 -0.0182 0.4279 11.00000 0.05 0.15
Q8 1 0.1196 0.0352 0.0334 11.00000 0.05 0.15
Q9 1 0.6017 0.1462 0.3175 11.00000 0.05 0.14
Q10 1 0.9202 0.3508 -0.0475 11.00000 0.05 0.14
Q11 1 0.2022 0.0338 -0.1746 11.00000 0.05 0.13
Q12 1 0.3204 0.0339 0.5394 11.00000 0.05 0.13
Q13 1 0.5000 0.0000 0.5000 10.50000 0.05 0.13
Q14 1 1.0778 0.3554 0.0673 11.00000 0.05 0.12
Q15 1 0.1752 0.2893 0.2268 11.00000 0.05 0.12
Q16 1 0.4338 0.0168 0.5369 11.00000 0.05 0.12
Q17 1 0.4226 0.1951 0.2387 11.00000 0.05 0.11
Q18 1 0.1578 0.2878 0.1892 11.00000 0.05 0.11
Q19 1 0.1578 0.0526 0.2825 11.00000 0.05 0.11
Q20 1 0.2425 0.0472 0.3468 11.00000 0.05 0.11
;
_shelx_res_checksum 13103
#######################################################################
#
# 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 \l/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 '\f and \w 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0502P)^2^+0.7905P] where P=(Fo^2^+2Fc^2^)/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 . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0339(2) 0.0945(5) 0.0311(2) -0.0070(3) 0.00892(17) 0.0025(3)
O1 0.0423(8) 0.1521(17) 0.0380(7) 0.0004(9) 0.0085(6) -0.0319(9)
O2 0.0522(10) 0.166(2) 0.0842(13) -0.0104(13) -0.0170(9) -0.0257(12)
O5 0.0408(8) 0.1583(18) 0.0415(8) 0.0029(9) 0.0180(6) 0.0021(9)
O3 0.0512(9) 0.1192(17) 0.0855(13) -0.0034(11) 0.0192(9) -0.0245(10)
N2 0.0326(8) 0.1156(16) 0.0313(8) 0.0008(9) 0.0057(6) -0.0168(9)
N1 0.0391(9) 0.0732(14) 0.0711(13) -0.0073(11) -0.0005(9) -0.0052(9)
C2 0.0362(9) 0.0552(13) 0.0485(11) -0.0045(9) 0.0023(8) -0.0018(9)
C1 0.0403(9) 0.0518(13) 0.0406(10) -0.0007(9) 0.0081(7) -0.0034(9)
C6 0.0377(9) 0.0479(12) 0.0386(9) -0.0031(8) 0.0050(7) -0.0030(8)
C7 0.0420(10) 0.0617(14) 0.0361(9) 0.0011(9) 0.0072(7) -0.0074(9)
C8 0.0391(9) 0.0712(15) 0.0355(9) -0.0007(9) 0.0072(7) -0.0093(10)
C9 0.0381(9) 0.0668(14) 0.0358(9) 0.0000(9) 0.0065(7) -0.0082(9)
C10 0.0344(8) 0.0486(12) 0.0358(9) 0.0005(8) 0.0072(7) -0.0021(8)
C15 0.0339(8) 0.0598(13) 0.0349(9) 0.0007(8) 0.0090(7) -0.0025(9)
C14 0.0370(9) 0.0774(16) 0.0393(10) 0.0028(10) 0.0038(7) -0.0092(10)
C13 0.0352(9) 0.0775(16) 0.0524(11) 0.0037(11) 0.0105(8) -0.0132(10)
C12 0.0441(10) 0.0798(16) 0.0463(11) 0.0065(11) 0.0171(8) -0.0119(11)
C11 0.0440(10) 0.0669(15) 0.0350(9) 0.0018(9) 0.0090(8) -0.0078(10)
C5 0.0415(10) 0.0745(16) 0.0424(10) -0.0055(10) 0.0101(8) -0.0110(10)
C4 0.0576(13) 0.108(2) 0.0380(10) -0.0051(12) 0.0123(9) -0.0134(13)
C3 0.0521(12) 0.0894(18) 0.0408(11) -0.0088(11) -0.0017(9) -0.0061(12)
C16 0.0476(10) 0.0648(15) 0.0301(9) -0.0034(9) 0.0136(7) -0.0028(10)
C17 0.0420(10) 0.0707(16) 0.0550(12) 0.0053(11) 0.0117(9) 0.0048(10)
C21 0.0832(16) 0.085(2) 0.0402(11) -0.0049(12) 0.0189(11) -0.0219(15)
C18 0.0555(13) 0.095(2) 0.0800(17) 0.0161(16) 0.0189(12) 0.0167(15)
C20 0.141(3) 0.0597(18) 0.0599(16) 0.0030(13) 0.0329(17) 0.0010(19)
C19 0.096(2) 0.088(2) 0.0804(19) 0.0116(16) 0.0339(16) 0.0276(19)
O4 0.0590(9) 0.0773(12) 0.0605(9) -0.0232(8) 0.0076(7) 0.0081(8)
_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) . . . . ?
_iucr_refine_instructions_details
;
mo_g32_1_0m.res created by SHELXL-2014/7
TITL mo_G32_1_0m in P2(1)/c
CELL 0.71073 14.0149 7.6562 18.3805 90 101.242 90
ZERR 4 0.0016 0.0009 0.002 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 84 64 8 20 4
EQIV $1 +X,0.5-Y,0.5+Z
EQIV $2 +X,1+Y,+Z
EQIV $3 -1+X,1.5-Y,-0.5+Z
SIMU C16 C21 C20 C19 C18 C17
SIMU 0.005 0.01 2 O4 S1 O5
L.S. 10
PLAN 20
SIZE 0.095 0.224 0.462
TEMP 23
HTAB N2 O1
HTAB C8 O5_$1
HTAB C11 O5_$1
HTAB C5 O5_$1
HTAB C20 O4_$2
HTAB C19 O3_$3
HTAB
CONF
fmap 2
acta
MERG 2
REM
REM
REM
WGHT 0.050200 0.790500
FVAR 0.12443
S1 5 0.316104 0.196198 0.148569 11.00000 0.03387 0.09449 =
0.03108 -0.00703 0.00892 0.00253
O1 4 0.508514 0.268424 0.336526 11.00000 0.04226 0.15211 =
0.03802 0.00040 0.00850 -0.03186
O2 4 0.970820 0.511485 0.689394 11.00000 0.05223 0.16647 =
0.08424 -0.01040 -0.01696 -0.02565
O5 4 0.397037 0.248700 0.116880 11.00000 0.04082 0.15833 =
0.04148 0.00287 0.01796 0.00211
O3 4 0.944768 0.519707 0.571053 11.00000 0.05119 0.11922 =
0.08549 -0.00336 0.01917 -0.02450
N2 3 0.355468 0.212793 0.237234 11.00000 0.03263 0.11560 =
0.03126 0.00081 0.00569 -0.01680
AFIX 43
H2 2 0.413177 0.254611 0.250620 11.00000 -1.20000
AFIX 0
N1 3 0.918527 0.490781 0.629022 11.00000 0.03912 0.07320 =
0.07110 -0.00732 -0.00047 -0.00517
C2 1 0.818294 0.427121 0.626108 11.00000 0.03622 0.05515 =
0.04846 -0.00454 0.00231 -0.00179
C1 1 0.758945 0.405147 0.557505 11.00000 0.04027 0.05177 =
0.04056 -0.00066 0.00807 -0.00342
AFIX 43
H1 2 0.781680 0.431494 0.514511 11.00000 -1.20000
AFIX 0
C6 1 0.664584 0.343081 0.553252 11.00000 0.03768 0.04793 =
0.03863 -0.00313 0.00498 -0.00304
C7 1 0.603356 0.316308 0.479938 11.00000 0.04195 0.06166 =
0.03612 0.00108 0.00720 -0.00743
AFIX 43
H7 2 0.631186 0.345537 0.439593 11.00000 -1.20000
AFIX 0
C8 1 0.513845 0.256008 0.464126 11.00000 0.03911 0.07117 =
0.03549 -0.00067 0.00724 -0.00927
AFIX 43
H8 2 0.482366 0.224421 0.502257 11.00000 -1.20000
AFIX 0
C9 1 0.463003 0.238148 0.386171 11.00000 0.03815 0.06679 =
0.03576 0.00005 0.00649 -0.00818
C10 1 0.359224 0.183564 0.368740 11.00000 0.03439 0.04857 =
0.03583 0.00053 0.00716 -0.00209
C15 1 0.307874 0.167974 0.295068 11.00000 0.03389 0.05978 =
0.03487 0.00070 0.00904 -0.00253
C14 1 0.211513 0.111448 0.281008 11.00000 0.03702 0.07745 =
0.03931 0.00279 0.00383 -0.00924
AFIX 43
H14 2 0.178104 0.099014 0.232350 11.00000 -1.20000
AFIX 0
C13 1 0.165464 0.073841 0.339039 11.00000 0.03523 0.07750 =
0.05238 0.00375 0.01046 -0.01321
AFIX 43
H13 2 0.100943 0.037305 0.329096 11.00000 -1.20000
AFIX 0
C12 1 0.213848 0.089752 0.411364 11.00000 0.04412 0.07984 =
0.04635 0.00648 0.01705 -0.01193
AFIX 43
H12 2 0.182261 0.064736 0.450183 11.00000 -1.20000
AFIX 0
C11 1 0.309504 0.143072 0.425773 11.00000 0.04400 0.06693 =
0.03498 0.00175 0.00899 -0.00784
H11 2 0.342213 0.151978 0.476680 11.00000 -1.20000
C5 1 0.633246 0.306228 0.619155 11.00000 0.04146 0.07449 =
0.04240 -0.00548 0.01008 -0.01101
H5 2 0.569970 0.261833 0.618270 11.00000 -1.20000
C4 1 0.694345 0.329556 0.686818 11.00000 0.05759 0.10752 =
0.03801 -0.00515 0.01229 -0.01344
AFIX 43
H4 2 0.672290 0.303878 0.730161 11.00000 -1.20000
AFIX 0
C3 1 0.788163 0.390754 0.691062 11.00000 0.05205 0.08940 =
0.04079 -0.00879 -0.00167 -0.00607
H3 2 0.834289 0.408025 0.738435 11.00000 -1.20000
C16 1 0.223277 0.352520 0.124985 11.00000 0.04760 0.06478 =
0.03014 -0.00337 0.01356 -0.00284
C17 1 0.127582 0.297002 0.105357 11.00000 0.04197 0.07071 =
0.05504 0.00528 0.01175 0.00481
AFIX 43
H17 2 0.113091 0.178364 0.103929 11.00000 -1.20000
AFIX 0
C21 1 0.245404 0.527951 0.125347 11.00000 0.08318 0.08523 =
0.04022 -0.00494 0.01885 -0.02186
AFIX 43
H21 2 0.309629 0.565726 0.137236 11.00000 -1.20000
AFIX 0
C18 1 0.054241 0.417795 0.088025 11.00000 0.05545 0.09478 =
0.07999 0.01608 0.01894 0.01672
AFIX 43
H18 2 -0.010038 0.380843 0.074960 11.00000 -1.20000
AFIX 0
C20 1 0.169273 0.647824 0.107468 11.00000 0.14080 0.05965 =
0.05989 0.00304 0.03288 0.00099
AFIX 43
H20 2 0.182500 0.766859 0.107502 11.00000 -1.20000
AFIX 0
C19 1 0.075161 0.589839 0.089895 11.00000 0.09606 0.08823 =
0.08040 0.01165 0.03394 0.02756
AFIX 43
H19 2 0.024788 0.670529 0.079059 11.00000 -1.20000
AFIX 0
O4 4 0.272462 0.028626 0.131215 11.00000 0.05904 0.07732 =
0.06050 -0.02325 0.00765 0.00809
HKLF 4
REM mo_G32_1_0m in P2(1)/c
REM R1 = 0.0528 for 2976 Fo > 4sig(Fo) and 0.0857 for all 3950 data
REM 271 parameters refined using 48 restraints
END
WGHT 0.0501 0.7936
REM Instructions for potential hydrogen bonds
HTAB N2 O1
HTAB C8 O5_$1
HTAB C14 O4
REM Highest difference peak 0.254, deepest hole -0.319, 1-sigma level 0.041
Q1 1 0.2576 0.2770 0.1395 11.00000 0.05 0.25
Q2 1 0.2424 0.7031 0.1228 11.00000 0.05 0.23
Q3 1 0.3609 0.2847 0.1379 11.00000 0.05 0.22
Q4 1 0.4108 0.1686 0.3754 11.00000 0.05 0.16
Q5 1 0.4757 0.3575 0.3441 11.00000 0.05 0.16
Q6 1 0.4147 0.3561 0.1312 11.00000 0.05 0.15
Q7 1 0.9560 0.3812 0.7002 11.00000 0.05 0.15
Q8 1 0.7151 0.3095 0.5521 11.00000 0.05 0.15
Q9 1 0.5457 0.3704 0.4708 11.00000 0.05 0.15
Q10 1 0.1449 0.6851 0.1083 11.00000 0.05 0.14
Q11 1 0.4863 0.2596 0.4279 11.00000 0.05 0.14
Q12 1 0.6539 0.2839 0.5755 11.00000 0.05 0.14
Q13 1 0.2528 0.1948 0.2913 11.00000 0.05 0.13
Q14 1 0.6404 0.3033 0.5219 11.00000 0.05 0.13
Q15 1 0.3199 0.0737 0.1200 11.00000 0.05 0.13
Q16 1 0.2300 0.4196 0.1292 11.00000 0.05 0.13
Q17 1 0.8066 0.3546 0.6495 11.00000 0.05 0.13
Q18 1 0.1904 0.3176 0.1259 11.00000 0.05 0.12
Q19 1 0.6931 0.4531 0.5545 11.00000 0.05 0.12
Q20 1 0.3401 0.1219 0.3908 11.00000 0.05 0.12
REM The information below was added by Olex2.
REM
REM R1 = 0.0528 for 2976 Fo > 4sig(Fo) and 0.0857 for all 32426 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.25, deepest hole -0.32
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0857
REM R1_gt = 0.0528
REM wR_ref = 0.1193
REM GOOF = 1.047
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 32426
REM Reflections_gt = 2976
REM Parameters = n/a
REM Hole = -0.32
REM Peak = 0.25
REM Flack = n/a
;
_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 \l/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 '\f and \w 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0470P)^2^+0.3270P] where P=(Fo^2^+2Fc^2^)/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 . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0409(3) 0.0983(4) 0.0610(3) -0.0196(3) 0.0053(2) -0.0291(3)
Cl1 0.1012(6) 0.1647(9) 0.1629(9) -0.0885(7) 0.0708(6) -0.0598(6)
C1 0.0470(10) 0.0586(11) 0.0491(11) -0.0035(9) -0.0033(8) -0.0158(9)
O1 0.0663(10) 0.1494(17) 0.0767(11) -0.0560(11) 0.0100(8) -0.0548(11)
C10 0.0593(12) 0.0648(12) 0.0458(10) -0.0131(9) -0.0006(9) -0.0193(10)
O3 0.0488(8) 0.1015(12) 0.0932(12) -0.0317(10) 0.0236(8) -0.0158(8)
C6 0.0453(10) 0.0601(11) 0.0458(10) -0.0086(9) -0.0032(8) -0.0161(9)
C16 0.0503(11) 0.0702(13) 0.0575(11) -0.0253(10) 0.0112(9) -0.0339(10)
C8 0.0537(12) 0.0844(15) 0.0538(12) -0.0228(11) -0.0004(9) -0.0260(11)
C7 0.0550(12) 0.0779(14) 0.0496(11) -0.0142(10) -0.0021(9) -0.0271(11)
N1 0.0520(10) 0.0939(14) 0.0518(11) -0.0126(10) 0.0013(8) -0.0307(10)
C5 0.0508(11) 0.0665(13) 0.0613(12) -0.0197(10) 0.0037(9) -0.0204(10)
O2 0.0637(10) 0.1611(18) 0.0744(11) -0.0285(11) -0.0041(8) -0.0635(11)
C2 0.0581(12) 0.0728(14) 0.0663(13) -0.0218(11) 0.0130(10) -0.0201(11)
C4 0.0614(13) 0.0688(14) 0.0793(15) -0.0311(12) 0.0023(11) -0.0231(11)
C11 0.0709(14) 0.0888(16) 0.0617(13) -0.0322(12) 0.0083(11) -0.0319(13)
C9 0.0589(12) 0.0744(14) 0.0537(12) -0.0182(10) -0.0024(10) -0.0249(11)
C3 0.0727(15) 0.0718(14) 0.0722(14) -0.0323(12) 0.0096(12) -0.0214(12)
C15 0.0735(15) 0.0839(16) 0.0661(14) -0.0307(12) 0.0033(12) -0.0298(13)
C21 0.0742(15) 0.0836(16) 0.0611(13) -0.0264(12) 0.0086(12) -0.0301(13)
C13 0.0742(16) 0.0823(16) 0.0753(15) -0.0260(13) 0.0222(13) -0.0273(13)
C12 0.0669(14) 0.0944(17) 0.0750(15) -0.0300(14) 0.0108(12) -0.0361(13)
C14 0.0906(19) 0.0952(19) 0.0794(17) -0.0461(15) 0.0212(14) -0.0306(15)
C20 0.103(2) 0.097(2) 0.0708(16) -0.0069(15) -0.0039(16) -0.0438(18)
C17 0.105(2) 0.0830(18) 0.0796(17) -0.0397(15) 0.0286(15) -0.0393(16)
C18 0.114(2) 0.0608(17) 0.140(3) -0.0378(18) 0.037(2) -0.0230(17)
C19 0.096(2) 0.0657(17) 0.123(3) -0.0040(17) 0.0065(19) -0.0320(16)
_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) . . ?
_iucr_refine_instructions_details
;
TITL mo_G27_0m in P-1 #2
mo_g27_0m.res
created by SHELXL-2017/1 at 13:56:14 on 14-Feb-2018
REM reset to P-1 #2
CELL 0.71073 8.413 9.8066 13.1211 73.231 85.049 69.892
ZERR 2 0.0004 0.0005 0.0007 0.002 0.002 0.002
LATT 1
SFAC C H Cl N O S
UNIT 42 32 2 2 6 2
L.S. 20
PLAN -10 0 0
SIZE 0.283 0.401 0.482
TEMP 23
BOND
fmap 2
acta
REM
REM
REM
WGHT 0.047000 0.327000
FVAR 0.18984
S1 6 0.500389 0.301880 0.819565 11.00000 0.04091 0.09830 =
0.06104 -0.01962 0.00527 -0.02912
CL1 3 1.824443 0.122708 0.299980 11.00000 0.10123 0.16473 =
0.16290 -0.08852 0.07083 -0.05980
C1 1 0.736291 0.440314 0.774955 11.00000 0.04697 0.05863 =
0.04908 -0.00349 -0.00326 -0.01584
O1 5 0.825366 0.323730 0.591612 11.00000 0.06634 0.14945 =
0.07665 -0.05604 0.01005 -0.05479
C10 1 1.316309 0.226398 0.458125 11.00000 0.05928 0.06482 =
0.04578 -0.01313 -0.00058 -0.01931
O3 5 0.402154 0.389755 0.887084 11.00000 0.04878 0.10152 =
0.09323 -0.03167 0.02360 -0.01583
C6 1 0.890484 0.425892 0.719661 11.00000 0.04529 0.06008 =
0.04582 -0.00860 -0.00317 -0.01609
C16 1 0.645322 0.137382 0.899642 11.00000 0.05027 0.07022 =
0.05747 -0.02534 0.01120 -0.03389
C8 1 1.104302 0.321605 0.587141 11.00000 0.05367 0.08437 =
0.05382 -0.02281 -0.00045 -0.02605
AFIX 43
H8 2 1.183983 0.345506 0.617054 11.00000 -1.20000
AFIX 0
C7 1 0.932058 0.355175 0.630130 11.00000 0.05499 0.07793 =
0.04962 -0.01424 -0.00212 -0.02711
N1 4 0.614019 0.393096 0.741061 11.00000 0.05197 0.09395 =
0.05180 -0.01255 0.00131 -0.03075
C5 1 1.003935 0.481492 0.752325 11.00000 0.05084 0.06647 =
0.06131 -0.01972 0.00366 -0.02041
AFIX 43
H5 2 1.104973 0.475845 0.716074 11.00000 -1.20000
AFIX 0
O2 5 0.417679 0.259217 0.749029 11.00000 0.06373 0.16112 =
0.07444 -0.02849 -0.00410 -0.06350
C2 1 0.705059 0.503494 0.859537 11.00000 0.05813 0.07276 =
0.06626 -0.02183 0.01299 -0.02013
AFIX 43
H2 2 0.603992 0.511726 0.896146 11.00000 -1.20000
AFIX 0
C4 1 0.971166 0.543890 0.835821 11.00000 0.06136 0.06879 =
0.07926 -0.03113 0.00234 -0.02311
AFIX 43
H4 2 1.049354 0.579327 0.856090 11.00000 -1.20000
AFIX 0
C11 1 1.442273 0.274012 0.482210 11.00000 0.07092 0.08878 =
0.06166 -0.03216 0.00830 -0.03186
AFIX 43
H11 2 1.421599 0.327905 0.532581 11.00000 -1.20000
AFIX 0
C9 1 1.150584 0.259029 0.507951 11.00000 0.05894 0.07444 =
0.05374 -0.01817 -0.00237 -0.02485
AFIX 43
H9 2 1.069486 0.233131 0.481217 11.00000 -1.20000
AFIX 0
C3 1 0.821258 0.553864 0.889748 11.00000 0.07275 0.07179 =
0.07217 -0.03231 0.00958 -0.02141
AFIX 43
H3 2 0.799051 0.595170 0.947101 11.00000 -1.20000
AFIX 0
C15 1 1.351728 0.146031 0.382708 11.00000 0.07349 0.08393 =
0.06613 -0.03075 0.00329 -0.02980
AFIX 43
H15 2 1.269505 0.112988 0.364793 11.00000 -1.20000
AFIX 0
C21 1 0.645522 0.108955 1.008152 11.00000 0.07419 0.08364 =
0.06108 -0.02639 0.00861 -0.03010
AFIX 43
H21 2 0.570994 0.178302 1.040615 11.00000 -1.20000
AFIX 0
C13 1 1.627352 0.163268 0.360015 11.00000 0.07424 0.08227 =
0.07534 -0.02597 0.02221 -0.02728
C12 1 1.596876 0.243534 0.433493 11.00000 0.06685 0.09441 =
0.07499 -0.03001 0.01079 -0.03611
AFIX 43
H12 2 1.679568 0.276995 0.450240 11.00000 -1.20000
AFIX 0
C14 1 1.506893 0.114394 0.333918 11.00000 0.09056 0.09516 =
0.07937 -0.04607 0.02120 -0.03065
AFIX 43
H14 2 1.529254 0.060205 0.283650 11.00000 -1.20000
AFIX 0
C20 1 0.758045 -0.024308 1.068972 11.00000 0.10347 0.09651 =
0.07081 -0.00688 -0.00389 -0.04382
AFIX 43
H20 2 0.756828 -0.045610 1.142791 11.00000 -1.20000
AFIX 0
C17 1 0.759009 0.035172 0.852545 11.00000 0.10528 0.08301 =
0.07959 -0.03968 0.02861 -0.03929
AFIX 43
H17 2 0.760231 0.054031 0.778884 11.00000 -1.20000
AFIX 0
C18 1 0.870947 -0.095261 0.915388 11.00000 0.11356 0.06085 =
0.13978 -0.03778 0.03738 -0.02303
AFIX 43
H18 2 0.948255 -0.164456 0.883983 11.00000 -1.20000
AFIX 0
C19 1 0.868803 -0.122971 1.022383 11.00000 0.09582 0.06573 =
0.12316 -0.00404 0.00653 -0.03203
AFIX 43
H19 2 0.944793 -0.211254 1.064171 11.00000 -1.20000
AFIX 0
H1 2 0.645255 0.359068 0.689556 11.00000 0.07037
HKLF 4
REM mo_G27_0m in P-1 #2
REM R1 = 0.0444 for 2917 Fo > 4sig(Fo) and 0.0646 for all 4007 data
REM 248 parameters refined using 0 restraints
END
WGHT 0.0467 0.3274
REM Highest difference peak 0.303, deepest hole -0.263, 1-sigma level 0.032
Q1 1 1.7406 0.2281 0.2581 11.00000 0.05 0.30
Q2 1 1.8103 0.0754 0.3578 11.00000 0.05 0.17
Q3 1 0.5746 0.2341 0.8845 11.00000 0.05 0.16
Q4 1 0.9662 0.4004 0.7576 11.00000 0.05 0.15
Q5 1 0.5092 0.2057 0.7478 11.00000 0.05 0.14
Q6 1 0.3964 0.4330 0.8168 11.00000 0.05 0.14
Q7 1 0.4019 0.3540 0.7341 11.00000 0.05 0.13
Q8 1 0.7295 0.3811 0.5809 11.00000 0.05 0.13
Q9 1 0.7749 -0.0539 0.8783 11.00000 0.05 0.13
Q10 1 0.8941 0.2521 0.6462 11.00000 0.05 0.13
REM The information below was added by Olex2.
REM
REM R1 = 0.0444 for 2917 Fo > 4sig(Fo) and 0.0646 for all 37156 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.30, deepest hole -0.26
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0646
REM R1_gt = 0.0444
REM wR_ref = 0.1211
REM GOOF = 1.022
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 37156
REM Reflections_gt = 2917
REM Parameters = n/a
REM Hole = -0.26
REM Peak = 0.30
REM Flack = n/a
;
_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 \l/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 '\f and \w 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0390P)^2^+1.2620P] where P=(Fo^2^+2Fc^2^)/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 . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0878(3) 0.0842(3) 0.0824(3) 0.00586(19) 0.01069(19) 0.0470(2)
Br1* 0.0901(3) 0.1344(4) 0.0867(3) 0.0052(2) 0.0491(2) -0.0088(3)
S2* 0.0337(3) 0.0532(4) 0.0573(4) 0.0167(3) 0.0113(3) 0.0109(3)
S2 0.0410(4) 0.0973(6) 0.0772(5) 0.0421(5) 0.0213(4) 0.0273(4)
O3* 0.0529(11) 0.0622(12) 0.0706(13) 0.0115(10) 0.0269(10) 0.0204(9)
O2* 0.0353(9) 0.0824(14) 0.0701(13) 0.0299(11) 0.0008(9) 0.0088(9)
O1 0.0473(11) 0.0853(15) 0.0817(15) 0.0389(12) 0.0193(10) 0.0177(10)
O1* 0.0440(11) 0.1226(19) 0.0530(12) 0.0241(12) 0.0044(9) 0.0043(11)
N1* 0.0402(12) 0.0578(14) 0.0535(16) 0.0197(12) 0.0083(11) 0.0048(10)
O3 0.0658(14) 0.1044(18) 0.0883(16) 0.0347(14) 0.0229(12) 0.0513(13)
O2 0.0420(11) 0.141(2) 0.117(2) 0.0776(18) 0.0268(12) 0.0191(13)
N1 0.0487(14) 0.088(2) 0.0772(19) 0.0427(16) 0.0210(12) 0.0272(14)
C6* 0.0395(13) 0.0421(13) 0.0506(15) 0.0146(11) 0.0082(11) 0.0081(10)
C16* 0.0339(12) 0.0439(14) 0.0475(14) 0.0075(11) 0.0029(10) 0.0029(10)
C1* 0.0401(13) 0.0369(13) 0.0530(15) 0.0130(11) 0.0090(11) 0.0068(10)
C10* 0.0519(15) 0.0407(13) 0.0485(15) 0.0145(11) 0.0102(12) 0.0090(11)
C7* 0.0412(14) 0.0554(16) 0.0534(16) 0.0198(13) 0.0072(12) 0.0103(12)
C8* 0.0430(14) 0.0606(17) 0.0518(16) 0.0180(13) 0.0095(12) 0.0130(12)
C9* 0.0469(14) 0.0511(15) 0.0557(17) 0.0179(13) 0.0082(12) 0.0079(12)
C7 0.0442(15) 0.0729(19) 0.0428(15) 0.0158(13) 0.0099(11) 0.0173(14)
C6 0.0465(14) 0.0614(16) 0.0386(14) 0.0091(12) 0.0114(11) 0.0186(12)
C1 0.0500(15) 0.0700(18) 0.0437(15) 0.0112(13) 0.0143(12) 0.0223(14)
C2* 0.0508(16) 0.0560(16) 0.0531(16) 0.0085(13) 0.0150(13) 0.0030(13)
C5* 0.0410(14) 0.0595(16) 0.0572(17) 0.0150(13) 0.0084(12) 0.0075(12)
C10 0.0541(16) 0.0602(17) 0.0428(15) 0.0175(12) 0.0079(12) 0.0161(13)
C8 0.0463(15) 0.0698(19) 0.0581(17) 0.0236(14) 0.0156(13) 0.0192(13)
C5 0.0486(16) 0.0622(18) 0.0547(17) 0.0058(14) 0.0063(13) 0.0150(13)
C9 0.0509(16) 0.0695(19) 0.0494(16) 0.0174(14) 0.0134(12) 0.0120(14)
C14* 0.0531(16) 0.0683(19) 0.0611(19) 0.0111(15) 0.0127(14) 0.0036(14)
C15* 0.0581(17) 0.0594(17) 0.0478(16) 0.0122(13) 0.0097(13) 0.0078(13)
C3* 0.0637(18) 0.0624(18) 0.0470(16) 0.0043(13) 0.0059(14) 0.0030(14)
C13 0.0638(18) 0.0610(18) 0.0474(16) 0.0090(13) 0.0047(13) 0.0233(15)
C4* 0.0452(15) 0.0646(18) 0.0588(18) 0.0087(14) -0.0010(13) 0.0013(13)
C13* 0.0645(19) 0.0593(18) 0.0617(19) 0.0123(14) 0.0261(15) 0.0052(14)
C16 0.0433(15) 0.0645(18) 0.076(2) 0.0218(15) 0.0165(14) 0.0014(13)
C21* 0.0692(19) 0.0567(17) 0.0507(17) 0.0105(13) 0.0087(14) 0.0104(14)
C11 0.0532(17) 0.0574(17) 0.076(2) 0.0261(15) 0.0063(14) 0.0128(14)
C11* 0.0546(16) 0.0681(19) 0.0527(17) 0.0162(14) 0.0068(13) 0.0058(14)
C4 0.0631(19) 0.0578(18) 0.0665(19) 0.0013(15) 0.0097(15) 0.0072(15)
C2 0.065(2) 0.0656(19) 0.0665(19) 0.0133(15) 0.0157(15) 0.0316(16)
C15 0.0632(18) 0.068(2) 0.073(2) 0.0290(16) 0.0183(15) 0.0129(15)
C12* 0.075(2) 0.080(2) 0.0461(16) 0.0125(15) 0.0139(15) 0.0035(17)
C12 0.0519(17) 0.0667(19) 0.072(2) 0.0213(16) 0.0055(14) 0.0125(14)
C3 0.079(2) 0.0505(17) 0.069(2) 0.0056(15) 0.0137(17) 0.0191(16)
C14 0.084(2) 0.0560(18) 0.072(2) 0.0229(16) 0.0133(17) 0.0171(17)
C19* 0.079(2) 0.0482(17) 0.097(3) 0.0166(18) 0.0020(19) 0.0159(16)
C17* 0.080(2) 0.0639(19) 0.0580(18) 0.0113(15) 0.0214(16) 0.0195(16)
C21 0.075(2) 0.077(2) 0.076(2) 0.0261(18) 0.0189(17) 0.0047(17)
C20* 0.097(3) 0.063(2) 0.069(2) 0.0235(17) 0.0048(18) 0.0167(18)
C18* 0.094(3) 0.0564(19) 0.083(3) -0.0017(18) 0.024(2) 0.0218(18)
C17 0.080(2) 0.070(2) 0.110(3) 0.023(2) 0.024(2) 0.0108(18)
C18 0.103(3) 0.074(3) 0.129(4) -0.014(2) 0.037(3) 0.000(2)
C20 0.105(3) 0.104(3) 0.076(2) 0.021(2) 0.025(2) -0.014(2)
C19 0.100(3) 0.111(3) 0.089(3) -0.009(2) 0.038(2) -0.023(3)
_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 . . ?
_iucr_refine_instructions_details
;
TITL mo_g33_1_0m_a.res in P-1
mo_g33_1_0m.res
created by SHELXL-2017/1 at 22:41:39 on 12-Feb-2018
REM Old TITL mo_G33_1_0m in P-1
REM SHELXT solution in P-1
REM R1 0.361, Rweak 0.070, Alpha 0.066, Orientation as input
REM Formula found by SHELXT: C20 N3 O3 S2 Cl2
CELL 0.71073 8.5051 12.1557 19.5199 101.955 99.056 92.558
ZERR 2 0.0009 0.0015 0.0024 0.004 0.004 0.004
LATT 1
SFAC C H Br N O S
UNIT 84 64 4 4 12 4
RIGU C21 C20 C19 C18 C17 C16
RIGU C17 C18 C19 C20 C21 C16
L.S. 12
PLAN -20 0 0
SIZE 0.289 0.301 0.42
TEMP 23
BOND $H
list 4
fmap 2
acta
SHEL 10 0.8
REM
REM
REM
WGHT 0.039000 1.262000
FVAR 0.43197
BR1 3 -0.267355 0.940613 0.070293 11.00000 0.08776 0.08415 =
0.08240 0.00586 0.01069 0.04695
BR1* 3 0.443242 0.182336 0.765840 11.00000 0.09010 0.13440 =
0.08673 0.00521 0.04912 -0.00884
S2* 6 1.503805 0.220447 0.379210 11.00000 0.03369 0.05316 =
0.05726 0.01669 0.01130 0.01092
S2 6 0.919335 0.392343 0.176533 11.00000 0.04105 0.09734 =
0.07716 0.04205 0.02131 0.02725
O3* 5 1.540981 0.161201 0.313479 11.00000 0.05288 0.06224 =
0.07057 0.01154 0.02691 0.02038
O2* 5 1.624531 0.243478 0.441387 11.00000 0.03531 0.08236 =
0.07009 0.02992 0.00082 0.00884
O1 5 0.584660 0.545640 0.081783 11.00000 0.04733 0.08531 =
0.08171 0.03895 0.01932 0.01765
O1* 5 1.230371 0.157723 0.514626 11.00000 0.04397 0.12265 =
0.05300 0.02414 0.00442 0.00435
N1* 4 1.359772 0.149595 0.401721 11.00000 0.04023 0.05779 =
0.05351 0.01970 0.00832 0.00482
O3 5 0.969719 0.281192 0.170968 11.00000 0.06577 0.10442 =
0.08825 0.03468 0.02290 0.05132
O2 5 1.021043 0.478038 0.161737 11.00000 0.04198 0.14065 =
0.11709 0.07759 0.02679 0.01906
N1 4 0.753279 0.388296 0.120367 11.00000 0.04873 0.08848 =
0.07716 0.04271 0.02100 0.02723
C6* 1 1.074144 0.118392 0.399261 11.00000 0.03949 0.04213 =
0.05056 0.01461 0.00818 0.00813
C16* 1 1.425648 0.347578 0.366178 11.00000 0.03387 0.04392 =
0.04746 0.00752 0.00293 0.00294
C1* 1 1.204486 0.122994 0.362742 11.00000 0.04011 0.03688 =
0.05297 0.01304 0.00898 0.00680
C10* 1 0.841831 0.163461 0.625387 11.00000 0.05186 0.04075 =
0.04852 0.01446 0.01017 0.00903
C7* 1 1.096239 0.142376 0.478130 11.00000 0.04118 0.05545 =
0.05340 0.01981 0.00718 0.01032
C8* 1 0.955899 0.147538 0.513940 11.00000 0.04300 0.06057 =
0.05175 0.01800 0.00946 0.01299
AFIX 43
H8* 2 0.854546 0.143275 0.486961 11.00000 -1.20000
AFIX 0
C9* 1 0.970245 0.158008 0.582999 11.00000 0.04689 0.05115 =
0.05570 0.01788 0.00819 0.00788
AFIX 43
H9* 2 1.073796 0.162481 0.607901 11.00000 -1.20000
AFIX 0
C7 1 0.461623 0.493942 0.088107 11.00000 0.04417 0.07290 =
0.04280 0.01585 0.00987 0.01728
C6 1 0.463358 0.379353 0.103780 11.00000 0.04650 0.06139 =
0.03856 0.00905 0.01139 0.01864
C1 1 0.608183 0.330118 0.121185 11.00000 0.05000 0.07004 =
0.04372 0.01123 0.01432 0.02225
C2* 1 1.177976 0.099960 0.288881 11.00000 0.05077 0.05596 =
0.05314 0.00849 0.01504 0.00301
AFIX 43
H2* 2 1.263749 0.103357 0.264940 11.00000 -1.20000
AFIX 0
C5* 1 0.921614 0.088308 0.358173 11.00000 0.04101 0.05947 =
0.05715 0.01503 0.00835 0.00754
AFIX 43
H5* 2 0.834261 0.083498 0.380993 11.00000 -1.20000
AFIX 0
C10 1 0.160143 0.713034 0.059998 11.00000 0.05414 0.06017 =
0.04285 0.01747 0.00793 0.01613
C8 1 0.309825 0.548841 0.081862 11.00000 0.04627 0.06983 =
0.05807 0.02356 0.01558 0.01918
AFIX 43
H8 2 0.219133 0.513462 0.091500 11.00000 -1.20000
AFIX 0
C5 1 0.321680 0.316683 0.103207 11.00000 0.04863 0.06219 =
0.05469 0.00582 0.00633 0.01499
AFIX 43
H5 2 0.225071 0.346909 0.091510 11.00000 -1.20000
AFIX 0
C9 1 0.299901 0.646549 0.062997 11.00000 0.05092 0.06945 =
0.04939 0.01744 0.01345 0.01198
AFIX 43
H9 2 0.390809 0.676496 0.050267 11.00000 -1.20000
AFIX 0
C14* 1 0.563173 0.145424 0.635898 11.00000 0.05310 0.06834 =
0.06107 0.01108 0.01274 0.00360
AFIX 43
H14* 2 0.456465 0.129420 0.614756 11.00000 -1.20000
AFIX 0
C15* 1 0.681561 0.139952 0.594884 11.00000 0.05812 0.05935 =
0.04785 0.01219 0.00968 0.00783
AFIX 43
H15* 2 0.653669 0.120077 0.545658 11.00000 -1.20000
AFIX 0
C3* 1 1.025615 0.072139 0.250875 11.00000 0.06372 0.06245 =
0.04703 0.00430 0.00588 0.00298
AFIX 43
H3* 2 1.009267 0.057536 0.201488 11.00000 -1.20000
AFIX 0
C13 1 -0.093746 0.847621 0.065339 11.00000 0.06381 0.06100 =
0.04739 0.00902 0.00475 0.02327
C4* 1 0.897626 0.065791 0.285335 11.00000 0.04524 0.06463 =
0.05876 0.00866 -0.00097 0.00132
AFIX 43
H4* 2 0.795181 0.046311 0.259376 11.00000 -1.20000
AFIX 0
C13* 1 0.605400 0.174927 0.708578 11.00000 0.06455 0.05929 =
0.06171 0.01230 0.02610 0.00522
C16 1 0.874045 0.439489 0.261957 11.00000 0.04326 0.06446 =
0.07601 0.02176 0.01646 0.00135
C21* 1 1.413585 0.375521 0.301010 11.00000 0.06916 0.05671 =
0.05073 0.01048 0.00871 0.01041
AFIX 43
H21* 2 1.447386 0.327892 0.263288 11.00000 -1.20000
AFIX 0
C11 1 0.010741 0.671153 0.067674 11.00000 0.05318 0.05738 =
0.07594 0.02614 0.00628 0.01284
AFIX 43
H11 2 -0.004112 0.596292 0.070985 11.00000 -1.20000
AFIX 0
C11* 1 0.879456 0.191604 0.699031 11.00000 0.05458 0.06805 =
0.05272 0.01617 0.00677 0.00580
AFIX 43
H11* 2 0.986007 0.206335 0.720616 11.00000 -1.20000
AFIX 0
C4 1 0.319571 0.211443 0.119361 11.00000 0.06309 0.05777 =
0.06649 0.00134 0.00973 0.00718
AFIX 43
H4 2 0.223022 0.171729 0.118543 11.00000 -1.20000
AFIX 0
C2 1 0.603696 0.223619 0.137239 11.00000 0.06525 0.06561 =
0.06652 0.01327 0.01571 0.03156
AFIX 43
H2 2 0.698811 0.191334 0.148508 11.00000 -1.20000
AFIX 0
C15 1 0.177420 0.824172 0.053410 11.00000 0.06325 0.06829 =
0.07321 0.02902 0.01829 0.01287
AFIX 43
H15 2 0.275308 0.853626 0.046754 11.00000 -1.20000
AFIX 0
C12* 1 0.762464 0.198201 0.740862 11.00000 0.07471 0.08027 =
0.04610 0.01250 0.01386 0.00355
AFIX 43
H12* 2 0.789342 0.218073 0.790124 11.00000 -1.20000
AFIX 0
C12 1 -0.115737 0.737649 0.070500 11.00000 0.05187 0.06668 =
0.07190 0.02129 0.00551 0.01252
AFIX 43
H12 2 -0.214824 0.708268 0.075844 11.00000 -1.20000
AFIX 0
C3 1 0.461625 0.165876 0.136678 11.00000 0.07908 0.05045 =
0.06922 0.00565 0.01365 0.01914
AFIX 43
H3 2 0.461105 0.095295 0.148090 11.00000 -1.20000
AFIX 0
C14 1 0.050654 0.892051 0.056610 11.00000 0.08437 0.05605 =
0.07211 0.02288 0.01326 0.01714
AFIX 43
H14 2 0.063663 0.966830 0.052869 11.00000 -1.20000
AFIX 0
C19* 1 1.302453 0.545169 0.347282 11.00000 0.07871 0.04820 =
0.09670 0.01662 0.00196 0.01586
AFIX 43
H19* 2 1.260638 0.612343 0.340684 11.00000 -1.20000
AFIX 0
C17* 1 1.376756 0.418398 0.422314 11.00000 0.08032 0.06391 =
0.05797 0.01130 0.02144 0.01946
AFIX 43
H17* 2 1.385449 0.399351 0.466436 11.00000 -1.20000
AFIX 0
C21 1 0.910753 0.377167 0.312743 11.00000 0.07455 0.07711 =
0.07643 0.02612 0.01886 0.00473
AFIX 43
H21 2 0.954828 0.308428 0.301466 11.00000 -1.20000
AFIX 0
C20* 1 1.350562 0.475324 0.292363 11.00000 0.09659 0.06255 =
0.06912 0.02355 0.00476 0.01673
AFIX 43
H20* 2 1.341050 0.494791 0.248344 11.00000 -1.20000
AFIX 0
C18* 1 1.314592 0.518165 0.412187 11.00000 0.09371 0.05635 =
0.08347 -0.00171 0.02369 0.02177
AFIX 43
H18* 2 1.281132 0.566745 0.449604 11.00000 -1.20000
AFIX 0
C17 1 0.806162 0.540858 0.278247 11.00000 0.08004 0.07009 =
0.11039 0.02334 0.02403 0.01084
AFIX 43
H17 2 0.779939 0.582422 0.243656 11.00000 -1.20000
AFIX 0
C18 1 0.777815 0.579573 0.346408 11.00000 0.10342 0.07354 =
0.12884 -0.01421 0.03725 -0.00039
AFIX 43
H18 2 0.731754 0.647424 0.358118 11.00000 -1.20000
AFIX 0
C20 1 0.881580 0.417576 0.380565 11.00000 0.10490 0.10414 =
0.07643 0.02072 0.02539 -0.01363
AFIX 43
H20 2 0.905891 0.375780 0.415176 11.00000 -1.20000
AFIX 0
C19 1 0.818075 0.517233 0.396997 11.00000 0.10009 0.11063 =
0.08899 -0.00857 0.03763 -0.02320
AFIX 43
H19 2 0.801188 0.544310 0.443216 11.00000 -1.20000
AFIX 0
H1* 2 1.366305 0.161157 0.440948 11.00000 0.05198
H1 2 0.751128 0.448251 0.112398 11.00000 0.04363
HKLF 4
REM mo_g33_1_0m_a.res in P-1
REM R1 = 0.0404 for 5855 Fo > 4sig(Fo) and 0.0604 for all 7942 data
REM 495 parameters refined using 36 restraints
END
WGHT 0.0388 1.2653
REM Highest difference peak 0.725, deepest hole -0.752, 1-sigma level 0.044
Q1 1 0.5011 0.1375 0.7830 11.00000 0.05 0.73
Q2 1 0.4767 0.2410 0.7636 11.00000 0.05 0.64
Q3 1 0.3887 0.1490 0.7269 11.00000 0.05 0.55
Q4 1 -0.3570 0.8929 0.0424 11.00000 0.05 0.32
Q5 1 1.4547 0.2817 0.3708 11.00000 0.05 0.29
Q6 1 0.9477 0.4729 0.1803 11.00000 0.05 0.23
Q7 1 -0.1866 0.9666 0.0489 11.00000 0.05 0.23
Q8 1 -0.2434 0.8811 0.0921 11.00000 0.05 0.22
Q9 1 -0.2296 0.9003 0.1063 11.00000 0.05 0.21
Q10 1 1.0847 0.1398 0.4356 11.00000 0.05 0.20
Q11 1 0.5275 0.1847 0.7191 11.00000 0.05 0.20
Q12 1 1.5035 0.1591 0.3369 11.00000 0.05 0.19
Q13 1 0.9834 0.3372 0.1613 11.00000 0.05 0.19
Q14 1 -0.1982 1.0588 0.1067 11.00000 0.05 0.18
Q15 1 -0.2683 0.8569 0.0815 11.00000 0.05 0.18
Q16 1 1.1337 0.1143 0.3824 11.00000 0.05 0.18
Q17 1 1.0046 0.1023 0.3816 11.00000 0.05 0.17
Q18 1 0.8887 0.4181 0.2261 11.00000 0.05 0.17
Q19 1 1.3849 0.3611 0.3893 11.00000 0.05 0.17
Q20 1 -0.1391 0.7738 0.1475 11.00000 0.05 0.16
REM The information below was added by Olex2.
REM
REM R1 = 0.0404 for 5855 Fo > 4sig(Fo) and 0.0604 for all 69007 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.73, deepest hole -0.75
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0604
REM R1_gt = 0.0404
REM wR_ref = 0.1017
REM GOOF = 1.029
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 69007
REM Reflections_gt = 5855
REM Parameters = n/a
REM Hole = -0.75
REM Peak = 0.73
REM Flack = n/a
;
_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 \l/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/[\s^2^(Fo^2^)+(0.0320P)^2^+1.1990P] where P=(Fo^2^+2Fc^2^)/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_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br 0.05127(16) 0.0891(2) 0.04662(15) 0.01395(13) 0.01937(11) -0.00021(13)
S 0.0395(3) 0.0430(3) 0.0336(3) 0.0045(2) 0.0125(2) 0.0054(2)
C5AA 0.0342(10) 0.0403(11) 0.0344(10) -0.0023(9) 0.0124(8) 0.0009(9)
C9AA 0.0395(11) 0.0473(12) 0.0276(9) 0.0041(9) 0.0061(8) 0.0052(9)
C1AA 0.0316(10) 0.0378(11) 0.0372(10) -0.0011(8) 0.0122(8) -0.0026(9)
C2AA 0.0334(10) 0.0388(11) 0.0410(11) -0.0001(9) 0.0114(9) 0.0073(9)
O0AA 0.0567(10) 0.0562(10) 0.0512(9) 0.0190(8) 0.0187(8) 0.0004(8)
C3AA 0.0339(10) 0.0443(12) 0.0429(11) 0.0038(9) 0.0110(9) 0.0088(9)
O 0.0611(10) 0.0587(10) 0.0435(9) -0.0012(8) 0.0185(8) 0.0153(8)
C4AA 0.0324(10) 0.0467(12) 0.0451(12) -0.0013(9) 0.0147(9) -0.0006(10)
C0AA 0.0341(11) 0.0611(15) 0.0429(12) -0.0048(10) 0.0128(9) -0.0016(10)
O5AA 0.0356(8) 0.0894(13) 0.0480(9) -0.0028(8) 0.0180(7) 0.0140(9)
C6AA 0.0331(10) 0.0527(14) 0.0407(11) -0.0006(9) 0.0091(9) 0.0049(10)
C7AA 0.0329(10) 0.0482(13) 0.0416(11) 0.0012(9) 0.0117(9) 0.0039(10)
C8AA 0.0361(11) 0.0728(17) 0.0468(12) -0.0007(11) 0.0200(10) 0.0114(12)
N1AA 0.0333(9) 0.0656(13) 0.0388(10) -0.0083(9) 0.0119(8) 0.0084(9)
C0BA 0.0450(12) 0.0631(15) 0.0401(12) -0.0007(11) 0.0149(10) 0.0130(11)
C1BA 0.0334(11) 0.0673(16) 0.0630(16) 0.0086(11) 0.0098(11) 0.0101(13)
C2BA 0.0288(10) 0.0654(15) 0.0443(12) -0.0003(10) 0.0115(9) 0.0088(11)
C3BA 0.0588(15) 0.0648(17) 0.0461(13) -0.0071(13) 0.0016(12) -0.0019(12)
C4BA 0.0551(14) 0.0594(16) 0.0387(12) 0.0159(12) 0.0068(10) -0.0005(11)
C8BA 0.0416(13) 0.0740(19) 0.0638(17) -0.0012(12) -0.0084(12) 0.0048(14)
C9BA 0.0446(12) 0.0507(13) 0.0458(12) -0.0034(10) 0.0132(10) 0.0005(10)
C0CA 0.0571(15) 0.0745(18) 0.0516(14) -0.0143(14) 0.0213(12) -0.0001(13)
C2 0.119(3) 0.0521(18) 0.068(2) -0.0194(19) -0.016(2) 0.0117(15)
C1 0.102(2) 0.0591(18) 0.0518(16) 0.0266(17) -0.0107(16) -0.0118(14)
C5BA 0.097(2) 0.087(2) 0.070(2) -0.045(2) 0.0168(18) 0.0061(18)
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) . . ?
_iucr_refine_fcf_details
;
data_mo_G23_3_0ma_CCDC1
_computing_structure_refinement 'olex2.refine (Bourhis et al., 2015)'
_shelx_refln_list_code 4
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
_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)'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_symmetry_space_group_name_Hall '-P 2ybc (x-z,y,z)'
_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)
loop_
_refln_index_h
_refln_index_k
_refln_index_l
_refln_F_squared_calc
_refln_F_squared_meas
_refln_F_squared_sigma
_refln_F_squared_weight
_refln_observed_status
-17 0 3 214.212 251.599 13.691 20.125 o
-17 0 5 69.904 92.106 11.539 44.410 o
-17 0 7 1.184 9.085 13.810 52.742 o
-17 0 9 328.497 333.273 34.005 6.192 o
-17 1 3 2.458 32.812 10.908 76.746 o
-17 1 4 90.669 102.134 10.371 44.787 o
-17 1 5 0.247 26.254 8.024 137.049 o
-17 1 6 558.180 633.522 16.050 7.891 o
-17 1 7 16.770 18.908 16.202 36.298 o
-17 1 8 477.900 498.405 23.474 7.503 o
-17 1 9 39.755 44.915 27.966 12.357 o
-16 0 -2 444.441 482.215 21.160 8.516 o
-16 0 0 229.744 284.069 13.922 18.597 o
-16 0 2 352.072 392.432 34.231 5.897 o
-16 0 4 163.981 198.598 17.497 18.793 o
-16 0 6 249.253 256.795 16.575 16.058 o
-16 0 8 68.160 84.954 18.368 23.880 o
-16 0 10 72.345 103.653 11.519 43.109 o
-16 0 12 355.826 351.868 13.058 14.223 o
-16 0 14 94.689 146.610 33.051 8.311 o
-16 1 -3 44.772 20.339 77.966 1.682 o
-16 1 -2 70.060 78.056 10.893 48.759 o
-16 1 -1 13.605 14.970 8.091 124.816 o
-16 1 0 97.984 107.568 7.707 53.877 o
-16 1 1 19.506 40.498 7.241 121.297 o
-16 1 2 71.200 83.728 13.492 37.026 o
-16 1 3 363.702 384.745 20.507 10.242 o
-16 1 4 16.440 12.521 11.177 71.882 o
-16 1 5 2.508 16.134 7.638 154.097 o
-16 1 6 174.298 178.649 11.211 27.990 o
-16 1 7 134.331 164.205 12.927 28.502 o
-16 1 8 175.592 166.432 13.287 24.889 o
-16 1 9 11.659 0.831 7.529 155.146 o
-16 1 10 5.211 5.229 7.460 166.329 o
-16 1 11 11.186 20.316 11.853 65.300 o
-16 1 12 42.246 48.693 10.283 63.991 o
-16 1 13 332.525 307.960 11.972 16.098 o
-16 2 -1 21.040 13.683 8.627 106.122 o
-16 2 0 350.431 391.336 14.112 13.354 o
-16 2 1 173.742 173.874 10.399 29.650 o
-16 2 2 60.170 77.330 9.836 57.164 o
-16 2 3 6.415 2.617 8.395 134.351 o
-16 2 4 58.647 63.755 8.544 69.093 o
-16 2 5 10.975 12.318 7.562 145.049 o
-16 2 6 43.118 44.761 8.817 78.010 o
-16 2 7 411.416 393.119 16.680 11.048 o
-16 2 8 0.056 -1.174 8.312 149.018 o
-16 2 9 218.807 255.680 11.165 22.568 o
-16 2 10 238.718 281.799 9.243 22.666 o
-16 2 11 218.690 189.934 8.681 27.777 o
-16 2 12 6.555 12.418 7.527 153.909 o
-16 3 1 129.026 149.199 9.497 37.896 o
-16 3 2 70.430 80.683 8.115 64.387 o
-16 3 3 16.196 33.453 8.758 99.520 o
-16 3 4 290.807 299.360 11.152 18.240 o
-16 3 5 44.258 43.094 8.799 78.048 o
-16 3 6 63.741 71.631 12.266 43.920 o
-16 3 7 3.827 10.354 7.994 144.793 o
-16 3 8 249.392 253.150 9.412 22.718 o
-16 3 9 93.594 100.116 9.821 46.679 o
-16 3 10 16.281 32.445 16.271 35.373 o
-15 0 -5 357.020 380.017 19.300 10.890 o
-15 0 -3 339.646 289.066 14.958 14.358 o
-15 0 -1 171.207 208.992 17.497 18.358 o
-15 0 1 42.353 65.428 9.412 68.153 o
-15 0 3 268.300 296.223 19.630 12.923 o
-15 0 5 371.399 361.993 20.427 10.325 o
-15 0 7 974.997 1031.340 37.541 2.852 o
-15 0 9 247.343 224.366 11.301 21.736 o
-15 0 11 536.711 549.483 17.393 8.235 o
-15 0 13 188.408 196.206 10.864 26.798 o
-15 0 15 8.500 13.915 12.491 61.139 o
-15 1 -6 1.730 -17.735 9.988 101.853 o
-15 1 -5 10.246 -7.594 7.835 147.958 o
-15 1 -4 429.461 417.899 12.952 11.929 o
-15 1 -3 10.158 10.829 7.417 152.456 o
-15 1 -2 0.313 -8.241 7.772 169.834 o
-15 1 -1 0.313 5.876 6.417 235.275 o
-15 1 0 212.211 254.642 11.881 22.152 o
-15 1 1 74.692 83.343 12.345 40.948 o
-15 1 2 33.579 45.714 9.403 76.322 o
-15 1 3 20.153 28.387 12.267 57.723 o
-15 1 4 87.936 116.900 7.725 55.249 o
-15 1 5 221.549 235.481 12.852 21.075 o
-15 1 6 630.159 630.892 12.559 7.801 o
-15 1 7 134.013 147.851 8.441 40.061 o
-15 1 8 64.910 75.541 9.013 61.277 o
-15 1 9 12.775 26.934 6.455 163.632 o
-15 1 10 342.957 335.653 9.702 16.584 o
-15 1 11 218.479 207.965 7.978 27.938 o
-15 1 12 16.140 29.800 7.793 119.812 o
-15 1 13 79.361 101.445 10.787 45.173 o
-15 1 14 162.597 156.101 8.512 35.378 o
-15 1 15 41.895 33.833 8.524 84.964 o
-15 1 16 224.331 199.157 11.051 24.024 o
-15 2 -5 0.205 -16.793 9.362 117.323 o
-15 2 -4 225.484 225.515 9.587 24.861 o
-15 2 -3 41.791 42.437 7.677 92.712 o
-15 2 -2 108.353 106.329 11.736 36.959 o
-15 2 -1 81.787 102.354 9.338 51.117 o
-15 2 0 5.445 7.567 7.412 165.214 o
-15 2 1 2.990 11.534 7.304 170.598 o
-15 2 2 238.887 248.187 11.736 21.116 o
-15 2 3 307.209 316.928 9.351 18.449 o
-15 2 4 40.384 46.856 6.957 101.725 o
-15 2 5 11.369 26.809 6.665 159.697 o
-15 2 6 264.055 261.649 9.739 21.396 o
-15 2 7 94.656 103.697 7.707 55.300 o
-15 2 8 4.348 7.861 8.859 121.011 o
-15 2 9 12.822 27.306 6.706 155.015 o
-15 2 10 184.315 162.158 7.264 34.689 o
-15 2 11 98.179 126.225 9.352 45.137 o
-15 2 12 297.704 330.160 8.823 18.893 o
-15 2 13 147.780 151.101 8.062 38.696 o
-15 2 14 33.035 43.079 7.620 99.965 o
-15 2 15 16.290 11.563 7.946 127.163 o
-15 3 -3 1.052 7.127 9.730 104.713 o
-15 3 -2 7.836 7.562 7.820 146.116 o
-15 3 -1 72.129 64.539 8.299 65.493 o
-15 3 0 7.524 15.625 7.672 144.617 o
-15 3 1 73.172 60.266 7.404 72.417 o
-15 3 2 2.173 4.842 9.561 108.333 o
-15 3 3 73.812 101.401 9.306 53.325 o
-15 3 4 534.613 584.814 15.793 8.431 o
-15 3 5 129.508 135.394 8.570 41.407 o
-15 3 6 17.581 13.617 9.965 86.513 o
-15 3 7 4.097 1.814 9.637 106.317 o
-15 3 8 0.751 3.004 8.487 139.517 o
-15 3 9 156.117 150.215 7.790 38.175 o
-15 3 10 20.727 27.355 7.063 132.202 o
-15 3 11 214.125 190.184 8.304 28.642 o
-15 3 12 1.627 16.446 8.450 129.862 o
-15 3 13 67.893 97.435 8.443 60.352 o
-15 4 -1 5.039 25.424 16.949 34.154 o
-15 4 0 3.241 14.330 7.537 158.061 o
-15 4 1 1.889 13.235 7.520 162.508 o
-15 4 2 146.622 153.901 9.194 36.019 o
-15 4 3 0.011 11.700 9.165 116.135 o
-15 4 4 23.262 33.816 7.721 111.410 o
-15 4 5 175.828 188.201 10.306 29.006 o
-15 4 6 70.023 88.598 9.247 56.342 o
-15 4 7 155.787 152.706 10.466 32.230 o
-15 4 8 331.794 322.048 10.370 16.832 o
-15 4 9 39.204 24.095 7.511 104.501 o
-15 4 10 41.006 58.168 9.121 72.825 o
-15 4 11 0.357 1.695 25.424 15.913 o
-14 0 -8 10.590 -1.646 11.316 75.429 o
-14 0 -6 374.564 361.596 15.585 12.454 o
-14 0 -4 95.778 96.495 9.819 46.617 o
-14 0 -2 25.976 17.512 9.285 89.943 o
-14 0 0 1188.810 1187.370 28.058 2.816 o
-14 0 2 491.204 497.043 22.110 7.750 o
-14 0 4 1098.290 1083.990 20.582 3.481 o
-14 0 6 6.610 9.413 7.795 147.430 o
-14 0 8 25.536 35.931 7.401 113.939 o
-14 0 10 982.651 944.241 20.994 4.013 o
-14 0 12 169.038 174.775 9.712 31.290 o
-14 0 14 394.970 431.132 17.020 10.874 o
-14 0 16 13.233 12.649 12.009 64.377 o
-14 0 18 195.847 174.238 33.051 7.602 o
-14 1 -8 13.112 17.950 9.565 94.183 o
-14 1 -7 80.666 77.197 9.715 52.506 o
-14 1 -6 145.479 151.979 9.501 35.567 o
-14 1 -5 5.384 -6.665 7.591 166.297 o
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8 6 9 59.785 56.654 9.436 63.198 o
8 6 10 9.832 -4.641 12.652 61.323 o
8 6 11 0.942 -5.807 11.033 84.100 o
8 7 8 15.384 -6.760 10.221 88.136 o
9 0 9 1.063 9.903 8.079 146.964 o
9 0 11 700.384 770.567 21.407 5.531 o
9 0 13 0.575 16.614 10.569 86.683 o
9 0 15 5.942 31.177 16.811 34.332 o
9 1 9 51.721 36.903 5.610 114.705 o
9 1 10 169.988 174.797 6.949 36.249 o
9 1 11 82.847 70.624 6.619 71.229 o
9 1 12 226.357 263.365 13.105 19.953 o
9 1 13 47.441 52.232 6.544 98.969 o
9 1 14 129.801 125.455 8.343 42.855 o
9 1 15 97.814 102.033 9.565 46.710 o
9 1 16 19.010 36.506 12.569 54.680 o
9 2 9 15.290 31.113 4.935 208.349 o
9 2 10 257.330 250.128 7.788 23.797 o
9 2 11 66.960 79.880 6.232 79.551 o
9 2 12 173.153 139.734 7.361 37.415 o
9 2 13 108.937 111.292 8.542 47.502 o
9 2 14 0.467 -3.422 8.366 146.384 o
9 2 15 1.229 1.367 9.330 116.302 o
9 3 9 809.870 728.228 13.665 5.878 o
9 3 10 23.948 21.436 6.240 153.295 o
9 3 11 4.225 5.640 6.474 216.590 o
9 3 12 26.553 26.524 6.851 129.611 o
9 3 13 118.175 131.327 8.731 43.180 o
9 3 14 99.155 101.198 9.169 48.141 o
9 3 15 119.596 116.799 10.210 39.477 o
9 4 9 14.071 15.244 6.807 161.225 o
9 4 10 322.474 303.452 14.492 14.899 o
9 4 11 16.894 14.774 7.229 143.190 o
9 4 12 263.094 243.439 14.540 17.567 o
9 4 13 112.302 120.317 11.529 36.232 o
9 4 14 36.982 52.103 18.480 26.164 o
9 5 9 35.397 29.583 8.532 90.320 o
9 5 10 7.204 5.909 8.004 142.615 o
9 5 11 55.681 42.358 8.157 78.836 o
9 5 12 50.035 47.230 12.985 44.795 o
9 6 9 71.819 47.503 12.359 44.156 o
9 6 10 16.952 -4.260 15.666 39.755 o
10 0 10 223.436 180.436 11.486 24.101 o
10 0 12 122.746 167.472 12.678 29.844 o
10 0 14 566.805 616.857 26.543 5.877 o
10 1 10 325.572 328.410 17.003 13.043 o
10 1 11 70.936 81.164 6.263 76.863 o
10 1 12 48.298 58.370 7.142 89.047 o
10 1 13 14.948 16.075 7.082 149.806 o
10 1 14 5.482 15.317 10.501 85.237 o
10 1 15 314.547 341.049 21.817 10.611 o
10 2 10 47.052 38.346 6.320 108.571 o
10 2 11 353.204 357.527 14.952 13.248 o
10 2 12 41.055 70.370 7.675 84.093 o
10 2 13 17.129 19.167 7.995 120.351 o
10 2 14 45.190 61.282 9.509 67.040 o
10 3 10 557.266 520.821 12.878 9.167 o
10 3 11 13.585 16.486 7.001 154.506 o
10 3 12 4.787 1.332 7.471 171.129 o
10 3 13 98.113 90.862 9.729 47.085 o
10 4 10 52.303 47.917 7.681 84.018 o
10 4 11 1.393 -6.476 8.032 156.969 o
10 4 12 0.829 1.534 9.454 113.638 o
10 5 10 2.522 -14.626 12.962 60.583 o
11 0 11 16.471 19.124 11.587 66.294 o
11 0 13 25.804 49.697 12.945 49.234 o
11 1 11 3.441 13.684 9.718 100.304 o
11 1 12 395.577 391.071 14.257 12.340 o
11 1 13 60.650 67.537 9.794 58.712 o
11 2 11 103.376 94.514 8.269 51.737 o
11 2 12 52.317 37.567 8.448 78.933 o
11 2 13 6.440 12.090 9.352 105.641 o
11 3 11 29.057 29.208 9.489 81.878 o
11 3 12 100.758 108.735 12.396 35.691 o
11 4 11 85.443 96.150 13.866 33.544 o
12 0 12 296.701 315.908 19.694 12.185 o
12 1 12 7.149 6.811 8.402 130.258 o
;
_iucr_refine_instructions_details
;
TITL mo_g23_3_0ma in P21/n #14
REM reset to P21/n #14
CELL 0.71073 13.8047 7.5462 18.9025 90 104.055 90
ZERR 4 0.0012 0.0007 0.0015 0 0.003 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O S Br
UNIT 84 64 4 12 4 4
L.S. 4
PLAN 20
SIZE 0.462 0.563 0.831
TEMP 23
BOND
FMAP 2
ACTA
WGHT 0.032 1.199
FVAR 0.108628
REM
REM
REM
Br 6 0.43234 0.43683 0.14684 11.00000 0.05127 0.08909 0.04662 =
-0.00021 0.01937 0.01395
S 5 -0.21863 0.64913 0.04793 11.00000 0.03954 0.04298 0.03365 =
0.00539 0.01254 0.00455
C5AA 1 -0.10292 0.55360 0.18097 11.00000 0.03417 0.04032 0.03435 =
0.00091 0.01240 -0.00227
C9AA 1 -0.26717 0.43676 0.02348 11.00000 0.03950 0.04729 0.02762 =
0.00519 0.00615 0.00411
C1AA 1 -0.00471 0.52725 0.22356 11.00000 0.03164 0.03778 0.03718 =
-0.00256 0.01224 -0.00110
C2AA 1 0.36826 0.56987 0.27047 11.00000 0.03342 0.03884 0.04105 =
0.00727 0.01136 -0.00011
O0AA 4 -0.28887 0.74226 0.07817 11.00000 0.05670 0.05621 0.05116 =
0.00038 0.01874 0.01901
C3AA 1 0.45010 0.51494 0.24463 11.00000 0.03394 0.04427 0.04291 =
0.00879 0.01104 0.00381
O 4 -0.18669 0.72364 -0.01220 11.00000 0.06110 0.05867 0.04349 =
0.01534 0.01852 -0.00119
C4AA 1 0.08418 0.57412 0.19583 11.00000 0.03242 0.04666 0.04513 =
-0.00056 0.01474 -0.00127
C0AA 1 0.18353 0.57486 0.24706 11.00000 0.03414 0.06112 0.04292 =
-0.00162 0.01280 -0.00479
AFIX 43
H0AA 2 0.18773 0.57977 0.29688 11.00000 -1.20000
AFIX 0
O5AA 4 0.07672 0.61296 0.13164 11.00000 0.03561 0.08938 0.04803 =
0.01395 0.01801 -0.00284
C6AA 1 0.00745 0.45512 0.29301 11.00000 0.03310 0.05273 0.04066 =
0.00494 0.00914 -0.00056
AFIX 43
H6AA 2 0.07173 0.43517 0.32125 11.00000 -1.20000
AFIX 0
C7AA 1 0.26635 0.56880 0.22451 11.00000 0.03293 0.04819 0.04158 =
0.00392 0.01169 0.00121
AFIX 43
H7AA 2 0.25949 0.56328 0.17438 11.00000 -1.20000
AFIX 0
C8AA 1 -0.16754 0.44532 0.28009 11.00000 0.03613 0.07283 0.04677 =
0.01136 0.01999 -0.00069
AFIX 43
H8AA 2 -0.22189 0.42018 0.29938 11.00000 -1.20000
AFIX 0
N1AA 3 -0.11602 0.62025 0.11019 11.00000 0.03326 0.06560 0.03882 =
0.00844 0.01194 -0.00830
AFIX 43
H1AA 2 -0.06215 0.65003 0.09801 11.00000 -1.20000
AFIX 0
C0BA 1 -0.07263 0.41246 0.32116 11.00000 0.04498 0.06307 0.04014 =
0.01296 0.01486 -0.00067
AFIX 43
H0BA 2 -0.06264 0.36214 0.36729 11.00000 -1.20000
AFIX 0
C1BA 1 0.54620 0.51550 0.28799 11.00000 0.03342 0.06734 0.06303 =
0.01007 0.00981 0.00859
AFIX 43
H1BA 2 0.59913 0.47769 0.26933 11.00000 -1.20000
AFIX 0
C2BA 1 -0.18362 0.51487 0.21082 11.00000 0.02881 0.06537 0.04428 =
0.00881 0.01146 -0.00029
AFIX 43
H2BA 2 -0.24845 0.53610 0.18385 11.00000 -1.20000
AFIX 0
C3BA 1 0.48456 0.62888 0.38657 11.00000 0.05883 0.06482 0.04609 =
-0.00190 0.00161 -0.00714
AFIX 43
H3BA 2 0.49610 0.66748 0.43462 11.00000 -1.20000
AFIX 0
C4BA 1 -0.21883 0.32766 -0.01557 11.00000 0.05514 0.05941 0.03868 =
-0.00052 0.00679 0.01588
AFIX 43
H4BA 2 -0.16132 0.36536 -0.02849 11.00000 -1.20000
AFIX 0
C8BA 1 0.56310 0.57258 0.35922 11.00000 0.04158 0.07398 0.06376 =
0.00484 -0.00841 -0.00121
AFIX 43
H8BA 2 0.62764 0.57307 0.38883 11.00000 -1.20000
AFIX 0
C9BA 1 0.38903 0.62808 0.34287 11.00000 0.04462 0.05073 0.04582 =
0.00055 0.01320 -0.00342
AFIX 43
H9BA 2 0.33679 0.66732 0.36199 11.00000 -1.20000
AFIX 0
C0CA 1 -0.35333 0.38208 0.04178 11.00000 0.05715 0.07454 0.05155 =
-0.00015 0.02131 -0.01432
AFIX 43
H0CA 2 -0.38579 0.45671 0.06771 11.00000 -1.20000
AFIX 0
C2 1 -0.34319 0.10666 -0.01619 11.00000 0.11854 0.05213 0.06760 =
0.01168 -0.01635 -0.01942
AFIX 43
H2 2 -0.36852 -0.00607 -0.02924 11.00000 -1.20000
AFIX 0
C1 1 -0.25803 0.16092 -0.03500 11.00000 0.10153 0.05912 0.05181 =
-0.01182 -0.01069 0.02658
AFIX 43
H1 2 -0.22636 0.08508 -0.06102 11.00000 -1.20000
AFIX 0
C5BA 1 -0.39071 0.21551 0.02116 11.00000 0.09684 0.08718 0.06990 =
0.00608 0.01681 -0.04462
AFIX 43
H5BA 2 -0.44895 0.17779 0.03300 11.00000 -1.20000
AFIX 0
HKLF 4
END
Q1 1 0.466667 0.416667 0.183333 11 0.05 0.6
Q2 1 0.388889 0.375 0.15 11 0.05 0.41
Q3 1 0.044444 0.541667 0.216667 11 0.05 0.27
Q4 1 0.433333 0.5 0.133333 11 0.05 0.27
Q5 1 0.411111 0.541667 0.25 11 0.05 0.25
Q6 1 -0.055556 0.541667 0.2 11 0.05 0.24
Q7 1 -0.166667 0.541667 0.266667 11 0.05 0.24
Q8 1 0.333333 0.583333 0.25 11 0.05 0.23
Q9 1 -0.255556 0.5 0.016667 11 0.05 0.23
Q10 1 -0.144444 0.541667 0.2 11 0.05 0.23
REM The information below was added by Olex2.
REM
REM R1 = 0.0314 for 3318 Fo > 4sig(Fo) and 0.0410 for all 3940 data
REM 244 parameters refined using 0 restraints
REM Highest difference peak 0.6005, deepest hole -0.5137
REM Mean Shift 0.0000, Max Shift 0.0000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0410
REM R1_gt = 0.0314
REM wR_ref = 0.0778
REM GOOF = 1.0514
REM Shift_max = 0.0000
REM Shift_mean = 0.0000
REM Reflections_all = 3940
REM Reflections_gt = 3318
REM Parameters = 244
REM Hole = -0.5137
REM Peak = 0.6005
REM Flack = n/a
;
_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 t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w 34.00 98.00 1.00 8.44 -- 11.26-178.00 60.00 64
2 \w 34.00 98.00 1.00 8.44 -- 11.26-178.00 120.00 64
3 \w 34.00 98.00 1.00 8.44 -- 11.26-178.00 90.00 64
4 \w -40.00 62.00 1.00 8.44 -- -11.49 57.00-120.00 102
5 \w -84.00 17.00 1.00 8.44 -- -11.49 -57.00 90.00 101
6 \w -20.00 29.00 1.00 8.44 -- -11.49 -99.00-150.00 49
7 \w -65.00 44.00 1.00 8.44 -- 11.26 -77.00 150.00 109
8 \w -17.00 84.00 1.00 8.44 -- 11.26 57.00 -90.00 101
9 \w -20.00 29.00 1.00 8.44 -- -11.49 -99.00 -30.00 49
10 \w -87.00 -40.00 1.00 8.44 -- -11.49 155.00-133.00 47
11 \w -86.00 13.00 1.00 8.44 -- -11.49 -38.00 -60.00 99
12 \w -20.00 52.00 1.00 8.44 -- 11.26 -99.00 60.00 72
13 \w -20.00 52.00 1.00 8.44 -- 11.26 -99.00-150.00 72
14 \w -20.00 52.00 1.00 8.44 -- 11.26 -99.00 30.00 72
15 \w 18.00 88.00 1.00 8.44 -- 11.26-155.00-171.00 70
16 \w -20.00 29.00 1.00 8.44 -- -11.49 -99.00 120.00 49
17 \w -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 '\w 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0410P)^2^+0.9010P] where P=(Fo^2^+2Fc^2^)/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 . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0572(3) 0.0480(2) 0.0361(2) -0.00010(18) -0.01226(18) -0.0044(2)
N0AA 0.0614(10) 0.0452(9) 0.0428(8) -0.0017(7) -0.0080(7) -0.0047(8)
O1 0.0795(10) 0.0690(9) 0.0457(8) -0.0047(7) -0.0002(7) -0.0250(8)
C6 0.0406(9) 0.0456(9) 0.0425(9) -0.0025(7) -0.0056(7) 0.0037(7)
O4 0.0735(10) 0.0602(8) 0.0505(8) -0.0124(6) -0.0022(7) -0.0191(7)
O2 0.0946(11) 0.0587(8) 0.0377(7) 0.0074(6) -0.0065(7) -0.0105(8)
O3 0.0609(9) 0.0671(9) 0.0553(8) -0.0113(7) -0.0215(7) -0.0052(7)
C16 0.0462(10) 0.0512(10) 0.0451(9) 0.0044(8) -0.0012(8) -0.0059(8)
C1 0.0405(9) 0.0457(9) 0.0432(9) -0.0014(7) -0.0066(7) 0.0059(7)
C8 0.0598(12) 0.0538(11) 0.0426(9) -0.0038(8) -0.0053(8) -0.0051(9)
C9 0.0554(11) 0.0497(10) 0.0460(10) -0.0051(8) -0.0003(8) -0.0012(8)
C12 0.0610(12) 0.0466(10) 0.0455(10) -0.0034(8) 0.0024(8) -0.0064(9)
C2 0.0475(10) 0.0552(11) 0.0518(11) -0.0055(9) -0.0102(8) -0.0036(8)
C10 0.0512(10) 0.0403(9) 0.0475(10) -0.0062(7) -0.0023(8) -0.0004(8)
C13 0.0527(11) 0.0406(9) 0.0511(10) -0.0079(8) -0.0040(8) -0.0012(8)
C5 0.0512(11) 0.0608(11) 0.0427(10) -0.0038(8) -0.0031(8) 0.0006(9)
C7 0.0509(10) 0.0473(10) 0.0440(9) -0.0047(8) -0.0043(8) 0.0008(8)
C14 0.0590(12) 0.0499(10) 0.0576(11) -0.0052(9) 0.0027(9) -0.0165(9)
C3 0.0437(10) 0.0565(11) 0.0643(12) 0.0040(9) -0.0056(9) -0.0052(9)
C11 0.0565(11) 0.0432(9) 0.0527(11) -0.0053(8) 0.0005(9) -0.0093(8)
C15 0.0651(13) 0.0527(11) 0.0477(10) -0.0035(8) 0.0057(9) -0.0101(9)
C22 0.0694(13) 0.0530(11) 0.0517(11) -0.0060(9) -0.0027(10) 0.0004(10)
C4 0.0497(11) 0.0635(12) 0.0517(11) 0.0048(9) 0.0017(8) -0.0022(9)
C21 0.0605(14) 0.0559(13) 0.123(2) 0.0069(14) -0.0119(14) -0.0051(11)
C23 0.108(2) 0.0665(14) 0.0567(13) -0.0186(11) -0.0054(13) -0.0074(14)
C18 0.0603(16) 0.111(3) 0.146(3) 0.022(2) -0.0345(17) -0.0007(16)
C17 0.0593(14) 0.0706(15) 0.0997(19) 0.0057(13) -0.0247(13) -0.0076(11)
C20 0.084(2) 0.0632(16) 0.184(4) 0.033(2) -0.006(2) 0.0085(15)
C19 0.0653(17) 0.107(2) 0.153(3) 0.042(2) -0.0158(18) 0.0214(17)
_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) . . ?
_iucr_refine_instructions_details
;
TITL G241_UEG2 in P21/c #14
g241_ueg2.res
created by SHELXL-2017/1 at 22:17:08 on 12-Feb-2018
REM reset to P21/c #14
CELL 0.71073 8.838418 26.651384 8.774102 90 90.9627 90
ZERR 4 0.000521 0.001569 0.000418 0 0.0047 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 92 84 4 16 4
L.S. 20
PLAN 10 0 0
BOND
fmap 2
acta
SHEL 10 0.72
REM
REM
REM
WGHT 0.041000 0.901000
FVAR 5.11117
S1 5 0.508692 0.342961 0.407694 11.00000 0.05718 0.04798 =
0.03605 -0.00010 -0.01226 -0.00436
N0AA 3 0.458364 0.377499 0.552093 11.00000 0.06137 0.04522 =
0.04277 -0.00169 -0.00797 -0.00466
O1 4 0.616837 0.440770 0.714757 11.00000 0.07950 0.06898 =
0.04572 -0.00469 -0.00016 -0.02499
C6 1 0.453733 0.381188 0.829743 11.00000 0.04059 0.04556 =
0.04245 -0.00253 -0.00559 0.00366
O4 4 0.954189 0.584251 1.496632 11.00000 0.07349 0.06020 =
0.05051 -0.01242 -0.00217 -0.01913
O2 4 0.576656 0.377687 0.304922 11.00000 0.09464 0.05867 =
0.03768 0.00743 -0.00650 -0.01051
O3 4 0.382764 0.313731 0.355280 11.00000 0.06094 0.06708 =
0.05532 -0.01130 -0.02150 -0.00517
C16 1 0.649802 0.302289 0.478648 11.00000 0.04619 0.05121 =
0.04509 0.00444 -0.00120 -0.00589
C1 1 0.405843 0.358423 0.691717 11.00000 0.04052 0.04569 =
0.04316 -0.00138 -0.00659 0.00590
C8 1 0.619710 0.442691 0.981056 11.00000 0.05981 0.05380 =
0.04265 -0.00375 -0.00530 -0.00507
AFIX 43
H8 2 0.582241 0.428891 1.070163 11.00000 -1.20000
AFIX 0
C9 1 0.719463 0.479589 0.990555 11.00000 0.05541 0.04968 =
0.04601 -0.00507 -0.00034 -0.00116
AFIX 43
H9 2 0.756494 0.491244 0.898497 11.00000 -1.20000
AFIX 0
C12 1 0.785588 0.518729 1.400215 11.00000 0.06105 0.04665 =
0.04552 -0.00344 0.00239 -0.00637
AFIX 43
H12 2 0.751306 0.510637 1.496785 11.00000 -1.20000
AFIX 0
C2 1 0.305014 0.318406 0.693529 11.00000 0.04745 0.05519 =
0.05177 -0.00547 -0.01020 -0.00362
AFIX 43
H2 2 0.274201 0.303416 0.602461 11.00000 -1.20000
AFIX 0
C10 1 0.778642 0.504283 1.127367 11.00000 0.05121 0.04027 =
0.04751 -0.00620 -0.00227 -0.00043
C13 1 0.893770 0.555994 1.382513 11.00000 0.05267 0.04055 =
0.05108 -0.00792 -0.00405 -0.00120
C5 1 0.392820 0.362757 0.964541 11.00000 0.05118 0.06077 =
0.04272 -0.00380 -0.00306 0.00056
AFIX 43
H5 2 0.420468 0.377728 1.056613 11.00000 -1.20000
AFIX 0
C7 1 0.566693 0.422988 0.833495 11.00000 0.05088 0.04734 =
0.04399 -0.00471 -0.00428 0.00082
C14 1 0.946714 0.566265 1.238500 11.00000 0.05899 0.04986 =
0.05756 -0.00523 0.00271 -0.01651
AFIX 43
H14 2 1.021221 0.590486 1.225952 11.00000 -1.20000
AFIX 0
C3 1 0.250590 0.300881 0.829713 11.00000 0.04374 0.05653 =
0.06426 0.00401 -0.00563 -0.00518
AFIX 43
H3 2 0.184430 0.273748 0.830069 11.00000 -1.20000
AFIX 0
C11 1 0.729234 0.493759 1.273470 11.00000 0.05647 0.04321 =
0.05271 -0.00529 0.00053 -0.00925
AFIX 43
H11 2 0.655962 0.469146 1.286326 11.00000 -1.20000
AFIX 0
C15 1 0.890018 0.540945 1.113949 11.00000 0.06507 0.05274 =
0.04774 -0.00347 0.00568 -0.01012
AFIX 43
H15 2 0.926923 0.548456 1.017968 11.00000 -1.20000
AFIX 0
C22 1 0.901690 0.577365 1.647816 11.00000 0.06936 0.05299 =
0.05165 -0.00595 -0.00267 0.00044
AFIX 23
H22A 2 0.928518 0.544214 1.685040 11.00000 -1.20000
H22B 2 0.792558 0.580969 1.650482 11.00000 -1.20000
AFIX 0
C4 1 0.293162 0.323123 0.965118 11.00000 0.04966 0.06350 =
0.05168 0.00485 0.00168 -0.00219
AFIX 43
H4 2 0.254808 0.311443 1.056576 11.00000 -1.20000
AFIX 0
C21 1 0.631057 0.251600 0.474085 11.00000 0.06051 0.05594 =
0.12280 0.00687 -0.01188 -0.00510
AFIX 43
H21 2 0.543266 0.237676 0.432258 11.00000 -1.20000
AFIX 0
C23 1 0.977330 0.617153 1.743979 11.00000 0.10838 0.06649 =
0.05673 -0.01858 -0.00543 -0.00745
AFIX 137
H23A 2 0.955362 0.649618 1.701687 11.00000 -1.50000
H23B 2 1.084753 0.611794 1.745583 11.00000 -1.50000
H23C 2 0.940132 0.615432 1.846014 11.00000 -1.50000
AFIX 0
C18 1 0.891564 0.292383 0.593944 11.00000 0.06034 0.11098 =
0.14598 0.02160 -0.03446 -0.00074
AFIX 43
H18 2 0.980732 0.306067 0.633422 11.00000 -1.20000
AFIX 0
C17 1 0.779786 0.323276 0.539236 11.00000 0.05929 0.07058 =
0.09967 0.00573 -0.02469 -0.00762
AFIX 43
H17 2 0.791375 0.357940 0.542892 11.00000 -1.20000
AFIX 0
C20 1 0.744715 0.221113 0.532677 11.00000 0.08357 0.06319 =
0.18428 0.03274 -0.00590 0.00849
AFIX 43
H20 2 0.732839 0.186442 0.531983 11.00000 -1.20000
AFIX 0
C19 1 0.873010 0.241711 0.590926 11.00000 0.06533 0.10652 =
0.15314 0.04227 -0.01578 0.02139
AFIX 43
H19 2 0.949343 0.221027 0.629317 11.00000 -1.20000
AFIX 0
H0AA 2 0.518091 0.402404 0.561847 11.00000 0.06048
HKLF 4
REM G241_UEG2 in P21/c #14
REM R1 = 0.0544 for 4391 Fo > 4sig(Fo) and 0.0724 for all 5570 data
REM 267 parameters refined using 0 restraints
END
WGHT 0.0406 0.8998
REM Highest difference peak 0.283, deepest hole -0.294, 1-sigma level 0.037
Q1 1 0.5955 0.3210 0.4398 11.00000 0.05 0.28
Q2 1 0.4184 0.3774 0.7658 11.00000 0.05 0.21
Q3 1 0.3910 0.3289 0.7008 11.00000 0.05 0.21
Q4 1 0.5709 0.4401 0.9033 11.00000 0.05 0.19
Q5 1 0.4809 0.4072 0.8372 11.00000 0.05 0.19
Q6 1 0.7993 0.5493 1.3823 11.00000 0.05 0.19
Q7 1 0.7446 0.2298 0.4281 11.00000 0.05 0.18
Q8 1 0.9125 0.2655 0.5368 11.00000 0.05 0.17
Q9 1 0.4679 0.3632 0.4853 11.00000 0.05 0.17
Q10 1 0.6517 0.2790 0.4265 11.00000 0.05 0.17
REM The information below was added by Olex2.
REM
REM R1 = 0.0544 for 4391 Fo > 4sig(Fo) and 0.0724 for all 72423 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.28, deepest hole -0.29
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0724
REM R1_gt = 0.0544
REM wR_ref = 0.1307
REM GOOF = 1.110
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 72423
REM Reflections_gt = 4391
REM Parameters = n/a
REM Hole = -0.29
REM Peak = 0.28
REM Flack = n/a
;
_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