# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019
#######################################################################
#
# 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_tnx_aceton
_database_code_depnum_ccdc_archive 'CCDC 1538111'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record
;
2019-07-05 deposited with the CCDC. 2019-07-12 downloaded from the CCDC.
;
_audit_creation_date 2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common 'tenoxicam acetone solvate'
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H11 N3 O4 S2, C3 H6 O'
_chemical_formula_sum 'C16 H17 N3 O5 S2'
_chemical_formula_weight 395.44
_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 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 8.9341(4)
_cell_length_b 8.9659(5)
_cell_length_c 11.9315(6)
_cell_angle_alpha 75.325(4)
_cell_angle_beta 81.348(4)
_cell_angle_gamma 89.620(4)
_cell_volume 913.55(8)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 6678
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 29.3360
_cell_measurement_theta_min 3.8000
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.324
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.90682
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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 1.438
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 412
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.45
_exptl_crystal_size_min 0.2
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0282
_diffrn_reflns_av_unetI/netI 0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 15092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.877
_diffrn_reflns_theta_min 3.295
_diffrn_ambient_temperature 293.0
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_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 -83.00 -11.00 1.00 15.00 -- -11.43 147.00-108.90 72
2 \w -90.00 -18.00 1.00 15.00 -- -11.43 157.00 153.69 72
3 \w -90.00 -16.00 1.00 15.00 -- -11.43 156.00 -16.45 74
4 \w -58.00 41.00 1.00 15.00 -- 11.59 -57.00 150.00 99
5 \w -15.00 87.00 1.00 15.00 -- 11.59 38.00-150.00 102
6 \w -17.00 78.00 1.00 15.00 -- 11.59 57.00 -60.00 95
7 \w -13.00 90.00 1.00 15.00 -- 11.59 77.00 60.00 103
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3370
_reflns_number_total 4269
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.43 (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 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.281
_refine_diff_density_min -0.345
_refine_diff_density_rms 0.049
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 289
_refine_ls_number_reflns 4269
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0518
_refine_ls_R_factor_gt 0.0378
_refine_ls_restrained_S_all 1.052
_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^)+(0.0532P)^2^+0.1667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0971
_refine_ls_wR_factor_ref 0.1079
_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. Others
Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
3.a Idealised Me refined as rotating group:
C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
;
_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 0.64679(5) 0.55748(5) 0.81132(3) 0.04193(13) Uani 1 1 d . . . . .
S2 S 0.27683(5) 0.45221(6) 0.66354(4) 0.05121(15) Uani 1 1 d . . . . .
O3 O 0.60687(14) 0.68953(15) 0.85451(10) 0.0518(3) Uani 1 1 d . . . . .
O1 O 0.88141(13) 0.87648(14) 0.52662(10) 0.0512(3) Uani 1 1 d . . . . .
O2 O 0.44108(13) 0.74202(15) 0.50341(10) 0.0506(3) Uani 1 1 d . . . . .
N3 N 0.74324(15) 0.61764(15) 0.68037(11) 0.0399(3) Uani 1 1 d . . . . .
N2 N 0.68142(17) 0.92368(16) 0.42450(12) 0.0428(3) Uani 1 1 d . . . . .
H2 H 0.592(2) 0.888(2) 0.4218(17) 0.051 Uiso 1 1 d R . . . .
O4 O 0.72845(15) 0.43924(16) 0.87912(11) 0.0602(4) Uani 1 1 d . . . . .
N1 N 0.88008(16) 1.10430(16) 0.33983(12) 0.0432(3) Uani 1 1 d . . . . .
H1 H 0.925(2) 1.066(2) 0.3994(18) 0.052 Uiso 1 1 d R . . . .
C6 C 0.75133(18) 0.84071(18) 0.51692(14) 0.0395(4) Uani 1 1 d . . . . .
C9 C 0.44093(18) 0.54107(19) 0.67474(14) 0.0393(3) Uani 1 1 d . . . . .
C5 C 0.74400(18) 1.04460(18) 0.33679(13) 0.0386(3) Uani 1 1 d . . . . .
C7 C 0.66255(18) 0.71435(18) 0.59417(13) 0.0380(3) Uani 1 1 d . . . . .
C10 C 0.48391(19) 0.47792(19) 0.78157(14) 0.0412(4) Uani 1 1 d . . . . .
C13 C 0.8429(3) 0.5075(3) 0.63485(19) 0.0587(5) Uani 1 1 d . . . . .
H13A H 0.891(3) 0.445(3) 0.700(2) 0.088 Uiso 1 1 d R . . . .
H13B H 0.915(3) 0.568(3) 0.569(2) 0.088 Uiso 1 1 d R . . . .
H13C H 0.783(3) 0.438(3) 0.605(2) 0.088 Uiso 1 1 d R . . . .
C8 C 0.51527(18) 0.67263(19) 0.58291(13) 0.0388(3) Uani 1 1 d . . . . .
O5 O 0.9728(2) 0.1431(2) 0.7884(2) 0.1103(7) Uani 1 1 d . . . . .
C1 C 0.9503(2) 1.2214(2) 0.25378(17) 0.0514(4) Uani 1 1 d . . . . .
H1A H 1.041(2) 1.245(2) 0.2667(19) 0.062 Uiso 1 1 d R . . . .
C4 C 0.6711(2) 1.1111(2) 0.24150(15) 0.0482(4) Uani 1 1 d . . . . .
H4 H 0.575(2) 1.066(2) 0.2393(18) 0.058 Uiso 1 1 d R . . . .
C11 C 0.3863(2) 0.3577(2) 0.85458(17) 0.0549(5) Uani 1 1 d . . . . .
H11 H 0.394(2) 0.305(3) 0.931(2) 0.066 Uiso 1 1 d R . . . .
C2 C 0.8831(2) 1.2855(2) 0.15983(17) 0.0538(5) Uani 1 1 d . . . . .
H2A H 0.930(2) 1.367(3) 0.103(2) 0.065 Uiso 1 1 d R . . . .
C3 C 0.7409(2) 1.2303(2) 0.15438(16) 0.0514(4) Uani 1 1 d . . . . .
H3 H 0.689(2) 1.275(2) 0.0907(19) 0.062 Uiso 1 1 d R . . . .
C12 C 0.2703(2) 0.3321(2) 0.80033(18) 0.0599(5) Uani 1 1 d . . . . .
H12 H 0.192(3) 0.258(3) 0.824(2) 0.072 Uiso 1 1 d R . . . .
C14 C 0.7546(4) 0.0955(4) 0.7163(3) 0.0891(8) Uani 1 1 d . . . . .
H14A H 0.671(4) 0.168(4) 0.720(3) 0.134 Uiso 1 1 d R . . . .
H14B H 0.712(4) -0.006(4) 0.723(3) 0.134 Uiso 1 1 d R . . . .
H14C H 0.827(4) 0.146(4) 0.637(3) 0.134 Uiso 1 1 d R . . . .
C15 C 0.8457(3) 0.0907(2) 0.8108(2) 0.0697(6) Uani 1 1 d . . . . .
C16 C 0.782(2) 0.001(3) 0.9325(12) 0.111(5) Uani 0.58(6) 1 d . . P A 1
H16A H 0.846597 0.015698 0.986218 0.167 Uiso 0.58(6) 1 calc GR . P A 1
H16B H 0.774258 -0.106326 0.934893 0.167 Uiso 0.58(6) 1 calc GR . P A 1
H16C H 0.682569 0.037111 0.954222 0.167 Uiso 0.58(6) 1 calc GR . P A 1
C16A C 0.760(4) 0.046(3) 0.922(3) 0.199(16) Uani 0.42(6) 1 d . . P A 2
H16D H 0.787943 -0.054437 0.961682 0.298 Uiso 0.42(6) 1 calc GR . P A 2
H16E H 0.654428 0.044520 0.914851 0.298 Uiso 0.42(6) 1 calc GR . P A 2
H16F H 0.778455 0.118810 0.965754 0.298 Uiso 0.42(6) 1 calc GR . P A 2
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 0.0470(2) 0.0450(2) 0.0291(2) 0.00338(16) -0.01297(16) -0.00948(17)
S2 0.0504(3) 0.0627(3) 0.0427(3) -0.0147(2) -0.01142(19) -0.0142(2)
O3 0.0599(7) 0.0599(8) 0.0380(6) -0.0129(6) -0.0142(6) -0.0098(6)
O1 0.0481(7) 0.0542(7) 0.0416(7) 0.0119(5) -0.0170(5) -0.0119(5)
O2 0.0464(7) 0.0624(8) 0.0376(6) 0.0027(5) -0.0159(5) -0.0014(5)
N3 0.0405(7) 0.0403(7) 0.0328(7) 0.0043(5) -0.0098(5) -0.0016(5)
N2 0.0447(8) 0.0434(8) 0.0344(7) 0.0045(6) -0.0122(6) -0.0036(6)
O4 0.0619(8) 0.0614(8) 0.0445(7) 0.0175(6) -0.0209(6) -0.0067(6)
N1 0.0483(8) 0.0433(8) 0.0331(7) 0.0034(6) -0.0132(6) -0.0018(6)
C6 0.0449(9) 0.0406(9) 0.0301(8) -0.0010(6) -0.0100(7) 0.0004(7)
C9 0.0416(8) 0.0432(9) 0.0332(8) -0.0089(7) -0.0074(6) -0.0050(6)
C5 0.0452(9) 0.0365(8) 0.0312(8) -0.0020(6) -0.0086(6) 0.0028(6)
C7 0.0432(8) 0.0392(8) 0.0277(7) 0.0010(6) -0.0099(6) -0.0005(6)
C10 0.0469(9) 0.0415(9) 0.0328(8) -0.0041(6) -0.0074(7) -0.0086(7)
C13 0.0621(12) 0.0533(12) 0.0531(12) -0.0002(9) -0.0081(10) 0.0143(9)
C8 0.0435(9) 0.0433(9) 0.0287(8) -0.0060(6) -0.0084(6) 0.0010(7)
O5 0.0799(12) 0.0923(14) 0.173(2) -0.0491(14) -0.0372(13) -0.0090(10)
C1 0.0555(11) 0.0464(10) 0.0446(10) 0.0036(8) -0.0089(8) -0.0079(8)
C4 0.0525(10) 0.0508(10) 0.0377(9) 0.0007(7) -0.0155(8) 0.0004(8)
C11 0.0630(12) 0.0541(11) 0.0399(10) 0.0022(8) -0.0067(9) -0.0209(9)
C2 0.0653(12) 0.0458(10) 0.0396(10) 0.0077(8) -0.0062(8) -0.0030(8)
C3 0.0640(11) 0.0511(10) 0.0341(9) 0.0034(7) -0.0168(8) 0.0065(8)
C12 0.0632(12) 0.0597(12) 0.0515(11) -0.0048(9) -0.0069(9) -0.0249(10)
C14 0.100(2) 0.0711(17) 0.105(2) -0.0224(16) -0.0409(18) -0.0047(14)
C15 0.0821(16) 0.0430(11) 0.0881(18) -0.0211(11) -0.0177(13) -0.0039(10)
C16 0.179(11) 0.078(8) 0.069(4) -0.011(5) -0.005(4) -0.036(6)
C16A 0.44(5) 0.056(9) 0.094(10) -0.009(7) -0.029(13) -0.003(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 O3 1.4292(13) . ?
S1 N3 1.6275(14) . ?
S1 O4 1.4295(13) . ?
S1 C10 1.7464(16) . ?
S2 C9 1.7118(16) . ?
S2 C12 1.705(2) . ?
O1 C6 1.2373(19) . ?
O2 C8 1.2692(19) . ?
N3 C7 1.4465(19) . ?
N3 C13 1.476(2) . ?
N2 H2 0.87(2) . ?
N2 C6 1.395(2) . ?
N2 C5 1.357(2) . ?
N1 H1 0.86(2) . ?
N1 C5 1.341(2) . ?
N1 C1 1.349(2) . ?
C6 C7 1.423(2) . ?
C9 C10 1.368(2) . ?
C9 C8 1.473(2) . ?
C5 C4 1.395(2) . ?
C7 C8 1.405(2) . ?
C10 C11 1.411(2) . ?
C13 H13A 0.98(3) . ?
C13 H13B 0.98(3) . ?
C13 H13C 0.99(3) . ?
O5 C15 1.198(3) . ?
C1 H1A 0.89(2) . ?
C1 C2 1.349(3) . ?
C4 H4 0.96(2) . ?
C4 C3 1.364(3) . ?
C11 H11 0.92(2) . ?
C11 C12 1.351(3) . ?
C2 H2A 0.91(2) . ?
C2 C3 1.383(3) . ?
C3 H3 0.95(2) . ?
C12 H12 0.93(2) . ?
C14 H14A 0.99(4) . ?
C14 H14B 0.97(4) . ?
C14 H14C 1.07(4) . ?
C14 C15 1.478(4) . ?
C15 C16 1.498(14) . ?
C15 C16A 1.39(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
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 N3 107.92(7) . . ?
O3 S1 O4 118.44(8) . . ?
O3 S1 C10 108.98(8) . . ?
N3 S1 C10 101.43(7) . . ?
O4 S1 N3 108.73(8) . . ?
O4 S1 C10 109.97(8) . . ?
C12 S2 C9 91.66(9) . . ?
C7 N3 S1 115.36(11) . . ?
C7 N3 C13 114.08(14) . . ?
C13 N3 S1 117.73(12) . . ?
C6 N2 H2 115.1(13) . . ?
C5 N2 H2 118.7(13) . . ?
C5 N2 C6 126.11(15) . . ?
C5 N1 H1 118.7(13) . . ?
C5 N1 C1 122.99(15) . . ?
C1 N1 H1 118.3(13) . . ?
O1 C6 N2 120.74(14) . . ?
O1 C6 C7 124.60(14) . . ?
N2 C6 C7 114.65(14) . . ?
C10 C9 S2 110.12(12) . . ?
C10 C9 C8 126.79(15) . . ?
C8 C9 S2 122.98(12) . . ?
N2 C5 C4 122.12(16) . . ?
N1 C5 N2 120.11(14) . . ?
N1 C5 C4 117.76(15) . . ?
C6 C7 N3 114.00(13) . . ?
C8 C7 N3 120.86(13) . . ?
C8 C7 C6 124.77(14) . . ?
C9 C10 S1 116.95(13) . . ?
C9 C10 C11 114.37(16) . . ?
C11 C10 S1 128.66(13) . . ?
N3 C13 H13A 108.5(15) . . ?
N3 C13 H13B 107.2(14) . . ?
N3 C13 H13C 110.0(15) . . ?
H13A C13 H13B 114(2) . . ?
H13A C13 H13C 109(2) . . ?
H13B C13 H13C 108(2) . . ?
O2 C8 C9 118.39(14) . . ?
O2 C8 C7 125.39(15) . . ?
C7 C8 C9 116.17(13) . . ?
N1 C1 H1A 112.5(14) . . ?
N1 C1 C2 120.17(18) . . ?
C2 C1 H1A 127.3(15) . . ?
C5 C4 H4 117.1(12) . . ?
C3 C4 C5 119.65(18) . . ?
C3 C4 H4 123.2(12) . . ?
C10 C11 H11 126.7(14) . . ?
C12 C11 C10 110.62(17) . . ?
C12 C11 H11 122.6(13) . . ?
C1 C2 H2A 119.8(14) . . ?
C1 C2 C3 118.87(17) . . ?
C3 C2 H2A 121.2(14) . . ?
C4 C3 C2 120.52(17) . . ?
C4 C3 H3 118.6(13) . . ?
C2 C3 H3 120.8(12) . . ?
S2 C12 H12 115.8(14) . . ?
C11 C12 S2 113.23(15) . . ?
C11 C12 H12 130.9(14) . . ?
H14A C14 H14B 109(3) . . ?
H14A C14 H14C 105(3) . . ?
H14B C14 H14C 116(3) . . ?
C15 C14 H14A 111(2) . . ?
C15 C14 H14B 110(2) . . ?
C15 C14 H14C 105.7(18) . . ?
O5 C15 C14 120.6(3) . . ?
O5 C15 C16 121.1(6) . . ?
O5 C15 C16A 125.8(13) . . ?
C14 C15 C16 117.9(6) . . ?
C16A C15 C14 112.6(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C16A H16D 109.5 . . ?
C15 C16A H16E 109.5 . . ?
C15 C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
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
_geom_hbond_publ_flag
N2 H2 O2 0.87(2) 1.86(2) 2.6098(19) 143.0(18) . yes
N1 H1 O1 0.86(2) 1.97(2) 2.6155(18) 130.9(17) . yes
N1 H1 O1 0.86(2) 2.18(2) 2.8767(18) 138.2(17) 2_776 yes
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 N3 C7 C6 139.80(13) . . . . ?
S1 N3 C7 C8 -46.84(19) . . . . ?
S1 C10 C11 C12 178.51(16) . . . . ?
S2 C9 C10 S1 -178.21(9) . . . . ?
S2 C9 C10 C11 0.3(2) . . . . ?
S2 C9 C8 O2 14.0(2) . . . . ?
S2 C9 C8 C7 -168.41(12) . . . . ?
O3 S1 N3 C7 -62.44(13) . . . . ?
O3 S1 N3 C13 158.17(14) . . . . ?
O3 S1 C10 C9 84.28(15) . . . . ?
O3 S1 C10 C11 -94.04(19) . . . . ?
O1 C6 C7 N3 -6.4(2) . . . . ?
O1 C6 C7 C8 -179.47(16) . . . . ?
N3 S1 C10 C9 -29.40(16) . . . . ?
N3 S1 C10 C11 152.28(18) . . . . ?
N3 C7 C8 O2 -173.18(16) . . . . ?
N3 C7 C8 C9 9.4(2) . . . . ?
N2 C6 C7 N3 172.41(14) . . . . ?
N2 C6 C7 C8 -0.7(2) . . . . ?
N2 C5 C4 C3 -178.50(17) . . . . ?
O4 S1 N3 C7 167.91(11) . . . . ?
O4 S1 N3 C13 28.51(16) . . . . ?
O4 S1 C10 C9 -144.36(14) . . . . ?
O4 S1 C10 C11 37.3(2) . . . . ?
N1 C5 C4 C3 1.6(3) . . . . ?
N1 C1 C2 C3 0.8(3) . . . . ?
C6 N2 C5 N1 -6.6(3) . . . . ?
C6 N2 C5 C4 173.52(16) . . . . ?
C6 C7 C8 O2 -0.6(3) . . . . ?
C6 C7 C8 C9 -177.93(16) . . . . ?
C9 S2 C12 C11 0.70(19) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C5 N2 C6 O1 1.7(3) . . . . ?
C5 N2 C6 C7 -177.21(16) . . . . ?
C5 N1 C1 C2 0.9(3) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C10 S1 N3 C7 52.03(13) . . . . ?
C10 S1 N3 C13 -87.37(15) . . . . ?
C10 C9 C8 O2 -161.84(17) . . . . ?
C10 C9 C8 C7 15.7(3) . . . . ?
C10 C11 C12 S2 -0.6(3) . . . . ?
C13 N3 C7 C6 -79.32(19) . . . . ?
C13 N3 C7 C8 94.05(19) . . . . ?
C8 C9 C10 S1 -1.9(3) . . . . ?
C8 C9 C10 C11 176.65(17) . . . . ?
C1 N1 C5 N2 177.99(17) . . . . ?
C1 N1 C5 C4 -2.1(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C12 S2 C9 C10 -0.58(15) . . . . ?
C12 S2 C9 C8 -177.05(16) . . . . ?
_shelx_res_file
;
TITL exp_46_a.res in P-1
txm_aceton.res
created by SHELXL-2017/1 at 12:34:52 on 15-Jan-2019
CELL 0.71073 8.934118 8.965934 11.931546 75.3248 81.3475 89.6204
ZERR 2 0.000363 0.000451 0.000566 0.0043 0.0037 0.0037
LATT 1
SFAC C H N O S
UNIT 32 34 6 10 4
EQIV $1 2-X,2-Y,1-Z
L.S. 10
PLAN 50
TEMP 19.85
HTAB N2 O2
HTAB N1 O1
HTAB N1 O1_$1
BOND
CONF
BOND $H
list 4
fmap 2
acta
SHEL 40 0.76
REM
REM
REM
WGHT 0.053200 0.166700
FVAR 5.10148 0.58043
S1 5 0.646788 0.557481 0.811325 11.00000 0.04697 0.04504 =
0.02915 0.00338 -0.01297 -0.00948
S2 5 0.276835 0.452210 0.663544 11.00000 0.05044 0.06268 =
0.04275 -0.01468 -0.01142 -0.01416
O3 4 0.606873 0.689534 0.854511 11.00000 0.05989 0.05989 =
0.03802 -0.01289 -0.01416 -0.00978
O1 4 0.881415 0.876477 0.526615 11.00000 0.04807 0.05424 =
0.04157 0.01188 -0.01702 -0.01192
O2 4 0.441081 0.742016 0.503409 11.00000 0.04641 0.06239 =
0.03757 0.00268 -0.01593 -0.00140
N3 3 0.743238 0.617643 0.680373 11.00000 0.04047 0.04027 =
0.03279 0.00427 -0.00978 -0.00165
N2 3 0.681418 0.923679 0.424497 11.00000 0.04467 0.04341 =
0.03440 0.00455 -0.01224 -0.00360
H2 2 0.591697 0.888050 0.421760 11.00000 -1.20000
O4 4 0.728449 0.439237 0.879120 11.00000 0.06188 0.06139 =
0.04453 0.01749 -0.02091 -0.00671
N1 3 0.880081 1.104300 0.339826 11.00000 0.04834 0.04330 =
0.03311 0.00343 -0.01320 -0.00181
H1 2 0.924855 1.066401 0.399396 11.00000 -1.20000
C6 1 0.751334 0.840712 0.516922 11.00000 0.04486 0.04061 =
0.03015 -0.00101 -0.01004 0.00042
C9 1 0.440933 0.541067 0.674736 11.00000 0.04160 0.04323 =
0.03324 -0.00889 -0.00739 -0.00499
C5 1 0.744003 1.044602 0.336787 11.00000 0.04525 0.03649 =
0.03119 -0.00202 -0.00856 0.00279
C7 1 0.662551 0.714352 0.594170 11.00000 0.04317 0.03923 =
0.02770 0.00102 -0.00988 -0.00049
C10 1 0.483907 0.477921 0.781569 11.00000 0.04691 0.04148 =
0.03279 -0.00411 -0.00742 -0.00860
C13 1 0.842948 0.507473 0.634852 11.00000 0.06212 0.05325 =
0.05313 -0.00023 -0.00808 0.01433
H13A 2 0.890941 0.445155 0.699508 11.00000 -1.50000
H13B 2 0.914936 0.567714 0.569149 11.00000 -1.50000
H13C 2 0.782521 0.437781 0.605167 11.00000 -1.50000
C8 1 0.515265 0.672633 0.582914 11.00000 0.04354 0.04330 =
0.02867 -0.00604 -0.00835 0.00102
O5 4 0.972823 0.143130 0.788369 11.00000 0.07988 0.09231 =
0.17292 -0.04905 -0.03718 -0.00898
C1 1 0.950340 1.221394 0.253777 11.00000 0.05553 0.04636 =
0.04456 0.00365 -0.00894 -0.00794
H1A 2 1.041177 1.245232 0.266691 11.00000 -1.20000
C4 1 0.671104 1.111147 0.241499 11.00000 0.05246 0.05076 =
0.03769 0.00073 -0.01554 0.00044
H4 2 0.574935 1.065980 0.239250 11.00000 -1.20000
C11 1 0.386259 0.357683 0.854580 11.00000 0.06297 0.05414 =
0.03989 0.00217 -0.00673 -0.02087
H11 2 0.394047 0.305103 0.930613 11.00000 -1.20000
C2 1 0.883068 1.285471 0.159832 11.00000 0.06533 0.04579 =
0.03962 0.00767 -0.00622 -0.00298
H2A 2 0.929583 1.367106 0.103082 11.00000 -1.20000
C3 1 0.740852 1.230331 0.154383 11.00000 0.06404 0.05111 =
0.03408 0.00335 -0.01679 0.00650
H3 2 0.689220 1.275274 0.090734 11.00000 -1.20000
C12 1 0.270306 0.332109 0.800334 11.00000 0.06316 0.05966 =
0.05149 -0.00481 -0.00685 -0.02490
H12 2 0.191536 0.258016 0.823732 11.00000 -1.20000
C14 1 0.754636 0.095482 0.716349 11.00000 0.09952 0.07113 =
0.10467 -0.02237 -0.04092 -0.00474
H14A 2 0.671347 0.168082 0.720271 11.00000 -1.50000
H14B 2 0.711752 -0.005851 0.723390 11.00000 -1.50000
H14C 2 0.827448 0.146332 0.636533 11.00000 -1.50000
C15 1 0.845674 0.090689 0.810792 11.00000 0.08207 0.04302 =
0.08808 -0.02109 -0.01772 -0.00394
PART 1
C16 1 0.781512 0.001261 0.932459 21.00000 0.17872 0.07767 =
0.06880 -0.01103 -0.00469 -0.03637
AFIX 137
H16A 2 0.846597 0.015698 0.986218 21.00000 -1.50000
H16B 2 0.774258 -0.106326 0.934893 21.00000 -1.50000
H16C 2 0.682569 0.037111 0.954222 21.00000 -1.50000
AFIX 0
PART 0
PART 2
C16A 1 0.760001 0.046477 0.921858 -21.00000 0.43658 0.05621 =
0.09410 -0.00947 -0.02887 -0.00254
AFIX 137
H16D 2 0.787943 -0.054437 0.961682 -21.00000 -1.50000
H16E 2 0.654428 0.044520 0.914851 -21.00000 -1.50000
H16F 2 0.778455 0.118810 0.965754 -21.00000 -1.50000
AFIX 0
HKLF 4
REM exp_46_a.res in P-1
REM R1 = 0.0378 for 3370 Fo > 4sig(Fo) and 0.0518 for all 4269 data
REM 289 parameters refined using 0 restraints
END
WGHT 0.0532 0.1667
REM Highest difference peak 0.281, deepest hole -0.345, 1-sigma level 0.049
Q1 1 0.5520 0.5180 0.7983 11.00000 0.05 0.28
Q2 1 0.6898 0.7810 0.5625 11.00000 0.05 0.18
Q3 1 0.5955 0.6998 0.5929 11.00000 0.05 0.18
Q4 1 0.4790 0.5144 0.7284 11.00000 0.05 0.18
Q5 1 0.6949 1.0814 0.2962 11.00000 0.05 0.18
Q6 1 0.6996 0.6609 0.6316 11.00000 0.05 0.18
Q7 1 0.3619 0.5194 0.6765 11.00000 0.05 0.17
Q8 1 0.4772 0.5887 0.6301 11.00000 0.05 0.17
Q9 1 0.4493 0.4038 0.8231 11.00000 0.05 0.16
Q10 1 0.7757 0.5761 0.6624 11.00000 0.05 0.16
Q11 1 0.6699 0.1351 0.9341 11.00000 0.05 0.16
Q12 1 0.5048 0.4399 0.7704 11.00000 0.05 0.15
Q13 1 0.7836 -0.0269 0.7014 11.00000 0.05 0.15
Q14 1 0.6631 0.6997 0.8976 11.00000 0.05 0.15
Q15 1 0.5808 0.7070 0.8043 11.00000 0.05 0.14
Q16 1 0.9235 0.1170 0.5753 11.00000 0.05 0.14
Q17 1 0.7057 0.5865 0.7259 11.00000 0.05 0.14
Q18 1 0.8244 1.0605 0.3230 11.00000 0.05 0.14
Q19 1 0.8810 -0.2202 0.8787 11.00000 0.05 0.14
Q20 1 0.6349 0.7162 0.8454 11.00000 0.05 0.13
Q21 1 0.5720 0.7178 0.8596 11.00000 0.05 0.13
Q22 1 0.8102 0.6561 0.6989 11.00000 0.05 0.13
Q23 1 0.7132 0.9011 0.4788 11.00000 0.05 0.13
Q24 1 0.5838 0.6133 0.8586 11.00000 0.05 0.13
Q25 1 0.3192 0.2234 0.6895 11.00000 0.05 0.13
Q26 1 0.9985 0.7806 0.5000 11.00000 0.05 0.12
Q27 1 0.6664 0.7914 0.7902 11.00000 0.05 0.12
Q28 1 0.7400 0.3778 0.8738 11.00000 0.05 0.12
Q29 1 0.3053 0.4055 0.5774 11.00000 0.05 0.12
Q30 1 0.6865 0.0379 0.9240 11.00000 0.05 0.12
Q31 1 0.9444 0.8422 0.5607 11.00000 0.05 0.12
Q32 1 0.2362 0.1248 0.7788 11.00000 0.05 0.12
Q33 1 0.8803 1.5748 0.0813 11.00000 0.05 0.12
Q34 1 0.8332 -0.0931 0.7050 11.00000 0.05 0.12
Q35 1 0.8296 1.2316 0.1438 11.00000 0.05 0.12
Q36 1 0.2370 0.4214 0.6036 11.00000 0.05 0.12
Q37 1 0.6407 0.7451 0.6254 11.00000 0.05 0.12
Q38 1 0.7238 0.9836 0.3828 11.00000 0.05 0.12
Q39 1 0.9760 0.5638 0.6532 11.00000 0.05 0.12
Q40 1 0.7624 0.0312 0.9873 11.00000 0.05 0.11
Q41 1 0.9237 0.2052 0.9816 11.00000 0.05 0.11
Q42 1 0.9035 1.3945 0.3370 11.00000 0.05 0.11
Q43 1 0.6585 0.1126 0.7780 11.00000 0.05 0.11
Q44 1 0.6421 0.6245 0.5382 11.00000 0.05 0.11
Q45 1 0.9267 0.5847 0.5962 11.00000 0.05 0.11
Q46 1 0.4933 0.5842 0.4566 11.00000 0.05 0.11
Q47 1 0.3256 0.1794 0.7766 11.00000 0.05 0.11
Q48 1 0.9357 1.1981 0.4458 11.00000 0.05 0.11
Q49 1 0.7531 0.6801 0.5185 11.00000 0.05 0.11
Q50 1 0.6334 1.3095 0.2276 11.00000 0.05 0.11
;
_shelx_res_checksum 10399
_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
;
#######################################################################
#
# 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_tnx_chcl3_II
_database_code_depnum_ccdc_archive 'CCDC 1904023'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record
;
2019-07-04 deposited with the CCDC. 2019-07-12 downloaded from the CCDC.
;
_audit_creation_date 2019-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common 'tenoxicam chloroform II solvate'
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H11 N3 O4 S2, 2(C H Cl3)'
_chemical_formula_sum 'C15 H13 Cl6 N3 O4 S2'
_chemical_formula_weight 576.10
_chemical_absolute_configuration syn
_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 0.0050 0.0020 '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 0.1750 0.1990 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0090 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0150 0.0080 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1470 0.1550 '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 orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 9.5960(19)
_cell_length_b 16.740(3)
_cell_length_c 28.301(6)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 4546.2(16)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 600
_cell_measurement_temperature 100.0(10)
_cell_measurement_theta_max 62.03
_cell_measurement_theta_min 3.156
_shelx_estimated_absorpt_T_max 0.961
_shelx_estimated_absorpt_T_min 0.878
_exptl_absorpt_coefficient_mu 1.332
_exptl_absorpt_correction_T_max 1
_exptl_absorpt_correction_T_min 0.759
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'XDS (Kabsch, 2010)'
_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 1.683
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 2320
_exptl_crystal_size_max 0.1
_exptl_crystal_size_mid 0.03
_exptl_crystal_size_min 0.03
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0638
_diffrn_reflns_av_unetI/netI 0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_l_max 36
_diffrn_reflns_limit_l_min -36
_diffrn_reflns_number 38347
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full 28.439
_diffrn_reflns_theta_max 31.009
_diffrn_reflns_theta_min 1.873
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type 'Rayonix SX165 CCD'
_diffrn_measurement_method /f
_diffrn_radiation_type synchrotron
_diffrn_radiation_wavelength 0.7937
_diffrn_source ?
_reflns_Friedel_coverage 0.792
_reflns_Friedel_fraction_full 0.962
_reflns_Friedel_fraction_max 0.955
_reflns_number_gt 7832
_reflns_number_total 10006
_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 1.216
_refine_diff_density_min -0.889
_refine_diff_density_rms 0.118
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.030
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 552
_refine_ls_number_reflns 10006
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0869
_refine_ls_R_factor_gt 0.0636
_refine_ls_restrained_S_all 1.030
_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^)+(0.0875P)^2^+11.7036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1623
_refine_ls_wR_factor_ref 0.1783
_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. Others
Fixed Sof: C15A(0.5) H15A(0.5) C1(0.5) H1(0.5)
3.a Ternary CH refined with riding coordinates:
C14B(H14B), C14A(H14A), C15B(H15B), C15A(H15A), C1(H1)
3.b Aromatic/amide H refined with riding coordinates:
N2B(H2B), N2A(H2A), N1B(H1B), N1A(H1A), C4A(H4A), C4B(H4B), C2B(H2BA),
C11B(H11B), C11A(H11A), C3A(H3A), C3B(H3B), C1B(H1BA), C12B(H12B), C1A(H1AA),
C2A(H2AA), C12A(H12A)
3.c Idealised Me refined as rotating group:
C13A(H13D,H13E,H13F), C13B(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_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
S1B S 1.0592(2) 0.86244(12) 0.91204(6) 0.0305(4) Uani 1 1 d . . . . .
S1A S 1.4248(2) 0.70239(13) 0.59746(6) 0.0328(5) Uani 1 1 d . . . . .
S2B S 1.4046(2) 0.70885(13) 0.91372(7) 0.0352(5) Uani 1 1 d . . . . .
Cl3B Cl 1.4729(3) 0.58646(14) 0.72999(7) 0.0434(5) Uani 1 1 d . . . . .
Cl2B Cl 1.5351(3) 0.49301(13) 0.81405(8) 0.0429(5) Uani 1 1 d . . . . .
S2A S 1.0592(3) 0.83938(14) 0.60731(7) 0.0363(5) Uani 1 1 d . . . . .
Cl5B Cl 1.1336(3) 0.61259(14) 0.99301(9) 0.0452(6) Uani 1 1 d . . . . .
Cl1B Cl 1.6294(3) 0.65681(13) 0.80670(8) 0.0421(5) Uani 1 1 d . . . . .
Cl4B Cl 1.2008(4) 0.44850(16) 1.01134(10) 0.0588(7) Uani 1 1 d . . . . .
Cl6B Cl 1.2202(3) 0.50990(18) 0.91624(9) 0.0591(7) Uani 1 1 d . . . . .
Cl5A Cl 0.8286(3) 0.47568(18) 1.01159(11) 0.0619(8) Uani 1 1 d . . . . .
Cl3A Cl 1.1872(3) 0.4662(2) 0.78946(11) 0.0679(9) Uani 1 1 d . . . . .
Cl1A Cl 0.9591(4) 0.4680(2) 0.72441(12) 0.0866(13) Uani 1 1 d . . . . .
Cl6A Cl 0.5613(4) 0.3995(3) 1.00345(10) 0.0807(11) Uani 1 1 d . . . . .
Cl4A Cl 0.6350(4) 0.5258(2) 0.93882(10) 0.0737(9) Uani 1 1 d . . . . .
Cl2A Cl 0.9350(4) 0.5404(2) 0.81818(15) 0.0870(12) Uani 1 1 d . . . . .
O3B O 1.1050(7) 0.9291(3) 0.88429(19) 0.0337(13) Uani 1 1 d . . . . .
O2A O 1.2030(7) 0.8371(4) 0.70180(19) 0.0340(13) Uani 1 1 d . . . . .
O1A O 1.6297(6) 0.7914(4) 0.71911(18) 0.0328(13) Uani 1 1 d . . . . .
O1B O 0.8614(7) 0.7756(4) 0.78863(19) 0.0359(14) Uani 1 1 d . . . . .
O4A O 1.5056(7) 0.6956(4) 0.55517(18) 0.0384(14) Uani 1 1 d . . . . .
O4B O 0.9746(7) 0.8773(4) 0.95278(19) 0.0352(13) Uani 1 1 d . . . . .
O3A O 1.3901(7) 0.6314(3) 0.6230(2) 0.0349(14) Uani 1 1 d . . . . .
O2B O 1.2709(7) 0.7027(4) 0.81762(19) 0.0360(13) Uani 1 1 d . . . . .
N2B N 1.0591(8) 0.7127(4) 0.7616(2) 0.0320(15) Uani 1 1 d . . . . .
H2B H 1.147010 0.702248 0.767872 0.038 Uiso 1 1 calc R . . . .
N3A N 1.5035(8) 0.7629(4) 0.6333(2) 0.0306(15) Uani 1 1 d . . . . .
N2A N 1.4262(8) 0.8334(4) 0.7532(2) 0.0302(15) Uani 1 1 d . . . . .
H2A H 1.334901 0.831050 0.750785 0.036 Uiso 1 1 calc R . . . .
N3B N 0.9782(8) 0.8003(4) 0.8772(2) 0.0319(15) Uani 1 1 d . . . . .
N1B N 0.8759(8) 0.7007(4) 0.7069(2) 0.0329(15) Uani 1 1 d . . . . .
H1B H 0.823979 0.728597 0.726546 0.039 Uiso 1 1 calc R . . . .
N1A N 1.6160(8) 0.8627(4) 0.8024(2) 0.0316(15) Uani 1 1 d . . . . .
H1A H 1.669879 0.837497 0.782144 0.038 Uiso 1 1 calc R . . . .
C8A C 1.2835(9) 0.8106(5) 0.6690(3) 0.0295(17) Uani 1 1 d . . . . .
C6A C 1.5020(9) 0.8031(5) 0.7157(2) 0.0277(16) Uani 1 1 d . . . . .
C6B C 0.9843(10) 0.7537(5) 0.7961(3) 0.0343(19) Uani 1 1 d . . . . .
C7A C 1.4218(9) 0.7904(5) 0.6734(3) 0.0298(17) Uani 1 1 d . . . . .
C5A C 1.4781(9) 0.8667(5) 0.7939(3) 0.0290(17) Uani 1 1 d . . . . .
C4A C 1.3923(10) 0.9041(5) 0.8265(3) 0.0332(18) Uani 1 1 d . . . . .
H4A H 1.294344 0.906203 0.821878 0.040 Uiso 1 1 calc R . . . .
C4B C 1.0943(10) 0.6471(5) 0.6869(3) 0.0333(18) Uani 1 1 d . . . . .
H4B H 1.190003 0.638808 0.693938 0.040 Uiso 1 1 calc R . . . .
C2B C 0.8979(10) 0.6321(5) 0.6347(3) 0.0354(19) Uani 1 1 d . . . . .
H2BA H 0.858859 0.611973 0.606245 0.042 Uiso 1 1 calc R . . . .
C8B C 1.1944(9) 0.7373(5) 0.8472(3) 0.0314(18) Uani 1 1 d . . . . .
C10B C 1.2048(10) 0.8057(5) 0.9279(3) 0.0319(18) Uani 1 1 d . . . . .
C10A C 1.2711(10) 0.7525(5) 0.5852(3) 0.0324(18) Uani 1 1 d . . . . .
C9A C 1.2194(10) 0.7992(5) 0.6219(3) 0.0325(18) Uani 1 1 d . . . . .
C11B C 1.2864(10) 0.8097(5) 0.9694(3) 0.0336(19) Uani 1 1 d . . . . .
H11B H 1.266877 0.843063 0.995770 0.040 Uiso 1 1 calc R . . . .
C11A C 1.1823(10) 0.7528(5) 0.5455(3) 0.0350(19) Uani 1 1 d . . . . .
H11A H 1.202738 0.725562 0.516855 0.042 Uiso 1 1 calc R . . . .
C9B C 1.2555(9) 0.7545(5) 0.8949(3) 0.0312(18) Uani 1 1 d . . . . .
C5B C 1.0089(10) 0.6868(5) 0.7185(3) 0.0334(19) Uani 1 1 d . . . . .
C7B C 1.0603(9) 0.7650(5) 0.8396(3) 0.0298(17) Uani 1 1 d . . . . .
C3A C 1.4532(10) 0.9383(5) 0.8661(3) 0.0342(19) Uani 1 1 d . . . . .
H3A H 1.395172 0.964196 0.888630 0.041 Uiso 1 1 calc R . . . .
C3B C 1.0382(10) 0.6196(5) 0.6449(3) 0.0355(19) Uani 1 1 d . . . . .
H3B H 1.095601 0.592112 0.622887 0.043 Uiso 1 1 calc R . . . .
C1B C 0.8169(10) 0.6734(5) 0.6658(3) 0.0351(19) Uani 1 1 d . . . . .
H1BA H 0.721326 0.683060 0.659161 0.042 Uiso 1 1 calc R . . . .
C14B C 1.4963(11) 0.5895(6) 0.7924(3) 0.038(2) Uani 1 1 d . . . . .
H14B H 1.407670 0.608307 0.807319 0.045 Uiso 1 1 calc R . . . .
C12B C 1.3966(10) 0.7590(5) 0.9664(3) 0.037(2) Uani 1 1 d . . . . .
H12B H 1.462690 0.752098 0.991024 0.044 Uiso 1 1 calc R . . . .
C1A C 1.6741(10) 0.8962(5) 0.8411(3) 0.036(2) Uani 1 1 d . . . . .
H1AA H 1.771899 0.892186 0.845745 0.044 Uiso 1 1 calc R . . . .
C2A C 1.5940(10) 0.9362(5) 0.8739(3) 0.036(2) Uani 1 1 d . . . . .
H2AA H 1.634649 0.961050 0.900748 0.043 Uiso 1 1 calc R . . . .
C12A C 1.0647(11) 0.7961(6) 0.5524(3) 0.039(2) Uani 1 1 d . . . . .
H12A H 0.993329 0.801895 0.529358 0.046 Uiso 1 1 calc R . . . .
C13A C 1.5919(10) 0.8269(5) 0.6112(3) 0.036(2) Uani 1 1 d . . . . .
H13D H 1.640236 0.804954 0.583557 0.054 Uiso 1 1 calc GR . . . .
H13E H 1.660596 0.845874 0.634194 0.054 Uiso 1 1 calc GR . . . .
H13F H 1.532514 0.871485 0.601300 0.054 Uiso 1 1 calc GR . . . .
C13B C 0.8821(10) 0.7421(6) 0.9012(3) 0.0371(19) Uani 1 1 d . . . . .
H13A H 0.937076 0.699342 0.915801 0.056 Uiso 1 1 calc GR . . . .
H13B H 0.818259 0.719091 0.877879 0.056 Uiso 1 1 calc GR . . . .
H13C H 0.828364 0.769898 0.925657 0.056 Uiso 1 1 calc GR . . . .
C14A C 1.0083(12) 0.4642(7) 0.7848(4) 0.052(3) Uani 1 1 d . . . . .
H14A H 0.975020 0.412149 0.798033 0.063 Uiso 1 1 calc R . . . .
C15B C 1.2412(11) 0.5328(6) 0.9765(3) 0.041(2) Uani 1 1 d . . . . .
H15B H 1.340502 0.548144 0.982230 0.049 Uiso 1 1 calc R . . . .
C15A C 0.6988(19) 0.4507(11) 0.9718(6) 0.036(4) Uani 0.5 1 d . . P A 2
H15A H 0.740114 0.411090 0.949332 0.043 Uiso 0.5 1 calc R . P A 2
C1 C 0.652(3) 0.4775(15) 0.9989(8) 0.059(6) Uani 0.5 1 d . . P A 1
H1 H 0.610874 0.516447 1.021680 0.071 Uiso 0.5 1 calc R . P A 1
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
S1B 0.0366(12) 0.0342(10) 0.0206(8) -0.0006(7) 0.0003(8) 0.0000(8)
S1A 0.0441(13) 0.0332(10) 0.0212(8) -0.0033(7) -0.0016(8) 0.0011(9)
S2B 0.0401(13) 0.0365(10) 0.0289(9) 0.0002(8) -0.0056(8) 0.0023(9)
Cl3B 0.0561(15) 0.0453(12) 0.0288(9) -0.0020(9) -0.0037(9) 0.0001(11)
Cl2B 0.0545(15) 0.0317(10) 0.0425(11) 0.0041(9) -0.0069(10) 0.0015(10)
S2A 0.0436(13) 0.0398(11) 0.0255(9) -0.0013(8) -0.0070(9) 0.0050(10)
Cl5B 0.0513(15) 0.0370(11) 0.0474(12) 0.0012(9) 0.0071(11) 0.0035(10)
Cl1B 0.0505(14) 0.0358(11) 0.0400(11) -0.0012(9) -0.0079(10) -0.0011(10)
Cl4B 0.077(2) 0.0396(13) 0.0600(16) 0.0115(11) 0.0131(14) 0.0081(13)
Cl6B 0.080(2) 0.0587(15) 0.0383(12) -0.0126(11) 0.0045(12) -0.0115(14)
Cl5A 0.0563(18) 0.0606(16) 0.0688(17) -0.0152(14) -0.0237(14) 0.0041(13)
Cl3A 0.0536(18) 0.091(2) 0.0590(16) -0.0236(15) 0.0022(13) 0.0045(16)
Cl1A 0.103(3) 0.097(3) 0.0591(17) 0.0394(17) -0.0367(18) -0.051(2)
Cl6A 0.063(2) 0.141(3) 0.0385(13) 0.0006(16) 0.0000(13) -0.031(2)
Cl4A 0.082(2) 0.094(2) 0.0446(14) -0.0032(15) -0.0170(14) 0.0044(19)
Cl2A 0.087(3) 0.068(2) 0.106(3) 0.0171(19) 0.037(2) 0.0295(19)
O3B 0.044(4) 0.031(3) 0.026(3) 0.002(2) 0.002(2) 0.001(3)
O2A 0.039(4) 0.041(3) 0.022(3) -0.005(2) 0.000(2) 0.003(3)
O1A 0.038(4) 0.038(3) 0.023(2) -0.003(2) -0.001(2) 0.003(3)
O1B 0.036(4) 0.046(4) 0.025(3) -0.006(2) -0.003(2) 0.007(3)
O4A 0.047(4) 0.048(4) 0.020(2) -0.006(2) 0.001(2) 0.005(3)
O4B 0.039(4) 0.045(3) 0.022(2) -0.004(2) 0.004(2) -0.004(3)
O3A 0.049(4) 0.028(3) 0.028(3) -0.002(2) -0.002(3) 0.000(3)
O2B 0.040(4) 0.042(3) 0.026(3) -0.003(3) -0.003(2) 0.005(3)
N2B 0.031(4) 0.041(4) 0.024(3) -0.005(3) 0.000(3) 0.001(3)
N3A 0.033(4) 0.036(4) 0.022(3) -0.001(3) 0.003(3) 0.001(3)
N2A 0.033(4) 0.036(4) 0.021(3) -0.004(3) -0.004(3) -0.003(3)
N3B 0.037(4) 0.035(4) 0.023(3) 0.001(3) 0.005(3) -0.002(3)
N1B 0.036(4) 0.039(4) 0.024(3) -0.006(3) -0.005(3) 0.006(3)
N1A 0.040(4) 0.031(3) 0.023(3) -0.004(3) -0.002(3) 0.002(3)
C8A 0.039(5) 0.026(4) 0.023(3) -0.004(3) -0.001(3) 0.002(3)
C6A 0.033(5) 0.028(4) 0.021(3) 0.000(3) 0.001(3) 0.004(3)
C6B 0.039(5) 0.041(5) 0.023(3) -0.002(3) 0.000(3) -0.002(4)
C7A 0.036(5) 0.033(4) 0.021(3) -0.001(3) 0.005(3) 0.002(4)
C5A 0.035(5) 0.032(4) 0.020(3) -0.003(3) -0.004(3) 0.001(3)
C4A 0.035(5) 0.038(4) 0.027(4) -0.003(3) 0.003(3) 0.003(4)
C4B 0.038(5) 0.035(4) 0.027(4) -0.001(3) 0.001(3) -0.001(4)
C2B 0.039(5) 0.039(5) 0.028(4) -0.004(3) 0.000(3) 0.003(4)
C8B 0.031(5) 0.039(4) 0.024(3) 0.004(3) 0.004(3) 0.004(4)
C10B 0.040(5) 0.032(4) 0.023(3) 0.002(3) 0.001(3) -0.006(4)
C10A 0.041(5) 0.033(4) 0.024(3) -0.003(3) 0.000(3) -0.001(4)
C9A 0.040(5) 0.036(4) 0.021(3) -0.004(3) 0.001(3) -0.003(4)
C11B 0.044(5) 0.031(4) 0.025(4) 0.000(3) -0.005(3) -0.006(4)
C11A 0.044(5) 0.037(4) 0.024(4) -0.003(3) -0.006(3) 0.005(4)
C9B 0.035(5) 0.033(4) 0.025(4) -0.001(3) -0.005(3) -0.002(4)
C5B 0.040(5) 0.037(5) 0.023(3) 0.004(3) -0.003(3) -0.001(4)
C7B 0.030(5) 0.033(4) 0.026(3) -0.003(3) 0.000(3) 0.003(3)
C3A 0.047(6) 0.035(4) 0.020(3) -0.006(3) -0.001(3) 0.000(4)
C3B 0.041(5) 0.034(4) 0.031(4) -0.001(3) 0.008(4) 0.001(4)
C1B 0.042(5) 0.041(5) 0.022(3) -0.002(3) -0.004(3) 0.005(4)
C14B 0.046(6) 0.042(5) 0.024(4) -0.001(3) 0.002(3) 0.008(4)
C12B 0.050(6) 0.035(4) 0.026(4) 0.000(3) -0.009(4) -0.004(4)
C1A 0.037(5) 0.042(5) 0.029(4) -0.008(3) -0.006(4) 0.003(4)
C2A 0.042(6) 0.040(5) 0.025(4) -0.007(3) -0.006(3) 0.002(4)
C12A 0.049(6) 0.041(5) 0.026(4) -0.001(3) -0.008(4) 0.004(4)
C13A 0.049(6) 0.036(4) 0.024(4) 0.005(3) 0.006(4) 0.000(4)
C13B 0.040(5) 0.045(5) 0.027(4) -0.002(3) 0.003(3) -0.008(4)
C14A 0.061(7) 0.047(6) 0.048(5) 0.013(4) -0.003(5) -0.022(5)
C15B 0.044(6) 0.040(5) 0.039(5) 0.001(4) 0.003(4) -0.002(4)
C15A 0.032(10) 0.038(9) 0.037(9) -0.007(7) -0.001(7) 0.004(8)
C1 0.071(16) 0.066(14) 0.040(10) -0.013(10) 0.014(11) -0.015(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
S1B O3B 1.434(6) . ?
S1B O4B 1.432(6) . ?
S1B N3B 1.630(7) . ?
S1B C10B 1.748(10) . ?
S1A O4A 1.431(6) . ?
S1A O3A 1.430(6) . ?
S1A N3A 1.621(7) . ?
S1A C10A 1.732(9) . ?
S2B C9B 1.707(9) . ?
S2B C12B 1.712(9) . ?
Cl3B C14B 1.781(8) . ?
Cl2B C14B 1.767(10) . ?
S2A C9A 1.728(10) . ?
S2A C12A 1.716(9) . ?
Cl5B C15B 1.752(10) . ?
Cl1B C14B 1.750(11) . ?
Cl4B C15B 1.766(10) . ?
Cl6B C15B 1.759(10) . ?
Cl5A C15A 1.731(18) . ?
Cl5A C1 1.73(3) . ?
Cl3A C14A 1.722(12) . ?
Cl1A C14A 1.774(11) . ?
Cl6A C15A 1.812(19) . ?
Cl6A C1 1.58(2) . ?
Cl4A C15A 1.680(19) . ?
Cl4A C1 1.89(2) . ?
Cl2A C14A 1.736(13) . ?
O2A C8A 1.287(10) . ?
O1A C6A 1.244(10) . ?
O1B C6B 1.253(11) . ?
O2B C8B 1.255(10) . ?
N2B H2B 0.8800 . ?
N2B C6B 1.392(11) . ?
N2B C5B 1.380(10) . ?
N3A C7A 1.454(10) . ?
N3A C13A 1.503(11) . ?
N2A H2A 0.8800 . ?
N2A C6A 1.383(10) . ?
N2A C5A 1.371(9) . ?
N3B C7B 1.452(10) . ?
N3B C13B 1.504(11) . ?
N1B H1B 0.8800 . ?
N1B C5B 1.337(12) . ?
N1B C1B 1.373(10) . ?
N1A H1A 0.8800 . ?
N1A C5A 1.347(11) . ?
N1A C1A 1.350(10) . ?
C8A C7A 1.376(12) . ?
C8A C9A 1.479(10) . ?
C6A C7A 1.438(11) . ?
C6B C7B 1.444(11) . ?
C5A C4A 1.386(11) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.389(11) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.384(12) . ?
C4B C3B 1.385(12) . ?
C2B H2BA 0.9500 . ?
C2B C3B 1.393(14) . ?
C2B C1B 1.362(12) . ?
C8B C9B 1.501(11) . ?
C8B C7B 1.384(12) . ?
C10B C11B 1.415(11) . ?
C10B C9B 1.357(12) . ?
C10A C9A 1.392(11) . ?
C10A C11A 1.411(11) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.358(13) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.355(13) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.369(14) . ?
C3B H3B 0.9500 . ?
C1B H1BA 0.9500 . ?
C14B H14B 1.0000 . ?
C12B H12B 0.9500 . ?
C1A H1AA 0.9500 . ?
C1A C2A 1.379(12) . ?
C2A H2AA 0.9500 . ?
C12A H12A 0.9500 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C13B H13A 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C14A H14A 1.0000 . ?
C15B H15B 1.0000 . ?
C15A H15A 1.0000 . ?
C1 H1 1.0000 . ?
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
O3B S1B N3B 108.2(3) . . ?
O3B S1B C10B 108.6(4) . . ?
O4B S1B O3B 118.7(4) . . ?
O4B S1B N3B 109.1(4) . . ?
O4B S1B C10B 110.0(4) . . ?
N3B S1B C10B 100.9(4) . . ?
O4A S1A N3A 108.7(4) . . ?
O4A S1A C10A 109.4(4) . . ?
O3A S1A O4A 118.8(4) . . ?
O3A S1A N3A 108.2(4) . . ?
O3A S1A C10A 107.8(4) . . ?
N3A S1A C10A 102.7(4) . . ?
C9B S2B C12B 90.8(4) . . ?
C12A S2A C9A 91.5(4) . . ?
C6B N2B H2B 116.8 . . ?
C5B N2B H2B 116.8 . . ?
C5B N2B C6B 126.4(8) . . ?
C7A N3A S1A 115.8(6) . . ?
C7A N3A C13A 113.9(7) . . ?
C13A N3A S1A 116.5(5) . . ?
C6A N2A H2A 116.5 . . ?
C5A N2A H2A 116.5 . . ?
C5A N2A C6A 127.0(8) . . ?
C7B N3B S1B 116.4(6) . . ?
C7B N3B C13B 113.6(7) . . ?
C13B N3B S1B 115.7(5) . . ?
C5B N1B H1B 118.5 . . ?
C5B N1B C1B 122.9(8) . . ?
C1B N1B H1B 118.5 . . ?
C5A N1A H1A 119.0 . . ?
C5A N1A C1A 122.0(8) . . ?
C1A N1A H1A 119.0 . . ?
O2A C8A C7A 126.7(7) . . ?
O2A C8A C9A 116.4(8) . . ?
C7A C8A C9A 116.8(7) . . ?
O1A C6A N2A 121.0(7) . . ?
O1A C6A C7A 124.6(7) . . ?
N2A C6A C7A 114.3(7) . . ?
O1B C6B N2B 120.8(7) . . ?
O1B C6B C7B 125.5(8) . . ?
N2B C6B C7B 113.7(8) . . ?
C8A C7A N3A 121.8(7) . . ?
C8A C7A C6A 123.8(7) . . ?
C6A C7A N3A 114.1(7) . . ?
N2A C5A C4A 121.8(8) . . ?
N1A C5A N2A 119.1(7) . . ?
N1A C5A C4A 119.1(7) . . ?
C5A C4A H4A 120.8 . . ?
C5A C4A C3A 118.4(9) . . ?
C3A C4A H4A 120.8 . . ?
C5B C4B H4B 120.5 . . ?
C3B C4B H4B 120.5 . . ?
C3B C4B C5B 119.0(9) . . ?
C3B C2B H2BA 120.2 . . ?
C1B C2B H2BA 120.2 . . ?
C1B C2B C3B 119.6(8) . . ?
O2B C8B C9B 117.4(8) . . ?
O2B C8B C7B 126.5(8) . . ?
C7B C8B C9B 116.0(7) . . ?
C11B C10B S1B 129.0(7) . . ?
C9B C10B S1B 117.0(6) . . ?
C9B C10B C11B 113.8(8) . . ?
C9A C10A S1A 115.2(6) . . ?
C9A C10A C11A 112.2(8) . . ?
C11A C10A S1A 132.6(7) . . ?
C8A C9A S2A 122.3(6) . . ?
C10A C9A S2A 110.9(6) . . ?
C10A C9A C8A 126.7(8) . . ?
C10B C11B H11B 124.8 . . ?
C12B C11B C10B 110.4(8) . . ?
C12B C11B H11B 124.8 . . ?
C10A C11A H11A 123.5 . . ?
C12A C11A C10A 113.0(7) . . ?
C12A C11A H11A 123.5 . . ?
C8B C9B S2B 121.5(6) . . ?
C10B C9B S2B 111.6(6) . . ?
C10B C9B C8B 126.9(8) . . ?
N2B C5B C4B 121.0(8) . . ?
N1B C5B N2B 119.7(8) . . ?
N1B C5B C4B 119.3(8) . . ?
C6B C7B N3B 113.9(7) . . ?
C8B C7B N3B 121.8(7) . . ?
C8B C7B C6B 123.9(7) . . ?
C4A C3A H3A 118.9 . . ?
C2A C3A C4A 122.3(8) . . ?
C2A C3A H3A 118.9 . . ?
C4B C3B C2B 120.2(8) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
N1B C1B H1BA 120.6 . . ?
C2B C1B N1B 118.8(9) . . ?
C2B C1B H1BA 120.6 . . ?
Cl3B C14B H14B 108.7 . . ?
Cl2B C14B Cl3B 110.1(5) . . ?
Cl2B C14B H14B 108.7 . . ?
Cl1B C14B Cl3B 109.8(5) . . ?
Cl1B C14B Cl2B 110.8(5) . . ?
Cl1B C14B H14B 108.7 . . ?
S2B C12B H12B 123.3 . . ?
C11B C12B S2B 113.4(6) . . ?
C11B C12B H12B 123.3 . . ?
N1A C1A H1AA 119.4 . . ?
N1A C1A C2A 121.1(9) . . ?
C2A C1A H1AA 119.4 . . ?
C3A C2A C1A 117.0(8) . . ?
C3A C2A H2AA 121.5 . . ?
C1A C2A H2AA 121.5 . . ?
S2A C12A H12A 123.8 . . ?
C11A C12A S2A 112.4(6) . . ?
C11A C12A H12A 123.8 . . ?
N3A C13A H13D 109.5 . . ?
N3A C13A H13E 109.5 . . ?
N3A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
N3B C13B H13A 109.5 . . ?
N3B C13B H13B 109.5 . . ?
N3B C13B H13C 109.5 . . ?
H13A C13B H13B 109.5 . . ?
H13A C13B H13C 109.5 . . ?
H13B C13B H13C 109.5 . . ?
Cl3A C14A Cl1A 109.7(6) . . ?
Cl3A C14A Cl2A 110.3(6) . . ?
Cl3A C14A H14A 107.9 . . ?
Cl1A C14A H14A 107.9 . . ?
Cl2A C14A Cl1A 112.9(7) . . ?
Cl2A C14A H14A 107.9 . . ?
Cl5B C15B Cl4B 109.3(5) . . ?
Cl5B C15B Cl6B 111.0(6) . . ?
Cl5B C15B H15B 108.9 . . ?
Cl4B C15B H15B 108.9 . . ?
Cl6B C15B Cl4B 110.0(5) . . ?
Cl6B C15B H15B 108.9 . . ?
Cl5A C15A Cl6A 108.4(10) . . ?
Cl5A C15A H15A 106.8 . . ?
Cl6A C15A H15A 106.8 . . ?
Cl4A C15A Cl5A 116.3(11) . . ?
Cl4A C15A Cl6A 111.3(10) . . ?
Cl4A C15A H15A 106.8 . . ?
Cl5A C1 Cl4A 106.3(12) . . ?
Cl5A C1 H1 105.5 . . ?
Cl6A C1 Cl5A 120.7(17) . . ?
Cl6A C1 Cl4A 112.3(13) . . ?
Cl6A C1 H1 105.5 . . ?
Cl4A C1 H1 105.5 . . ?
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
_geom_hbond_publ_flag
N2B H2B O2B 0.88 1.84 2.584(9) 140.6 . yes
N2A H2A O2A 0.88 1.88 2.591(9) 136.6 . yes
N1B H1B O1A 0.88 2.15 2.830(10) 133.5 1_455 yes
N1B H1B O1B 0.88 1.96 2.634(8) 132.5 . yes
N1A H1A O1A 0.88 1.98 2.645(8) 131.2 . yes
N1A H1A O1B 0.88 2.12 2.797(10) 133.5 1_655 yes
C14B H14B O2B 1.00 2.07 2.963(11) 146.8 . yes
C14A H14A O2A 1.00 2.12 2.962(12) 140.7 3_746 yes
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
S1B N3B C7B C6B -143.7(6) . . . . ?
S1B N3B C7B C8B 42.9(10) . . . . ?
S1B C10B C11B C12B -175.5(7) . . . . ?
S1B C10B C9B S2B 175.5(5) . . . . ?
S1B C10B C9B C8B -4.4(12) . . . . ?
S1A N3A C7A C8A -40.5(10) . . . . ?
S1A N3A C7A C6A 146.4(6) . . . . ?
S1A C10A C9A S2A -175.1(5) . . . . ?
S1A C10A C9A C8A 1.1(12) . . . . ?
S1A C10A C11A C12A 174.6(8) . . . . ?
O3B S1B N3B C7B 62.7(7) . . . . ?
O3B S1B N3B C13B -160.0(6) . . . . ?
O3B S1B C10B C11B 93.8(8) . . . . ?
O3B S1B C10B C9B -80.5(7) . . . . ?
O2A C8A C7A N3A -178.4(8) . . . . ?
O2A C8A C7A C6A -6.0(14) . . . . ?
O2A C8A C9A S2A 14.4(11) . . . . ?
O2A C8A C9A C10A -161.4(8) . . . . ?
O1A C6A C7A N3A -0.7(12) . . . . ?
O1A C6A C7A C8A -173.7(8) . . . . ?
O1B C6B C7B N3B 4.2(13) . . . . ?
O1B C6B C7B C8B 177.4(9) . . . . ?
O4A S1A N3A C7A 167.0(6) . . . . ?
O4A S1A N3A C13A 28.9(7) . . . . ?
O4A S1A C10A C9A -147.7(7) . . . . ?
O4A S1A C10A C11A 35.7(10) . . . . ?
O4B S1B N3B C7B -166.9(6) . . . . ?
O4B S1B N3B C13B -29.7(7) . . . . ?
O4B S1B C10B C11B -37.6(9) . . . . ?
O4B S1B C10B C9B 148.2(7) . . . . ?
O3A S1A N3A C7A -62.7(7) . . . . ?
O3A S1A N3A C13A 159.2(6) . . . . ?
O3A S1A C10A C9A 81.8(7) . . . . ?
O3A S1A C10A C11A -94.8(9) . . . . ?
O2B C8B C9B S2B -15.6(11) . . . . ?
O2B C8B C9B C10B 164.3(9) . . . . ?
O2B C8B C7B N3B 176.5(8) . . . . ?
O2B C8B C7B C6B 3.8(14) . . . . ?
N2B C6B C7B N3B -174.0(7) . . . . ?
N2B C6B C7B C8B -0.7(13) . . . . ?
N3A S1A C10A C9A -32.3(7) . . . . ?
N3A S1A C10A C11A 151.1(9) . . . . ?
N2A C6A C7A N3A 176.7(7) . . . . ?
N2A C6A C7A C8A 3.7(12) . . . . ?
N2A C5A C4A C3A -178.2(8) . . . . ?
N3B S1B C10B C11B -152.6(8) . . . . ?
N3B S1B C10B C9B 33.1(8) . . . . ?
N1A C5A C4A C3A 2.0(12) . . . . ?
N1A C1A C2A C3A 1.7(14) . . . . ?
C6A N2A C5A N1A -8.4(13) . . . . ?
C6A N2A C5A C4A 171.8(8) . . . . ?
C6B N2B C5B N1B -0.2(14) . . . . ?
C6B N2B C5B C4B 179.4(8) . . . . ?
C7A C8A C9A S2A -166.9(7) . . . . ?
C7A C8A C9A C10A 17.3(13) . . . . ?
C5A N2A C6A O1A 12.2(13) . . . . ?
C5A N2A C6A C7A -165.3(8) . . . . ?
C5A N1A C1A C2A 0.2(13) . . . . ?
C5A C4A C3A C2A -0.1(14) . . . . ?
C4A C3A C2A C1A -1.7(14) . . . . ?
C10B S1B N3B C7B -51.2(6) . . . . ?
C10B S1B N3B C13B 86.1(7) . . . . ?
C10B C11B C12B S2B 1.4(10) . . . . ?
C10A S1A N3A C7A 51.1(7) . . . . ?
C10A S1A N3A C13A -87.0(7) . . . . ?
C10A C11A C12A S2A 0.9(11) . . . . ?
C9A S2A C12A C11A 0.3(8) . . . . ?
C9A C8A C7A N3A 3.1(12) . . . . ?
C9A C8A C7A C6A 175.5(8) . . . . ?
C9A C10A C11A C12A -2.0(12) . . . . ?
C11B C10B C9B S2B 0.4(10) . . . . ?
C11B C10B C9B C8B -179.5(8) . . . . ?
C11A C10A C9A S2A 2.2(10) . . . . ?
C11A C10A C9A C8A 178.4(8) . . . . ?
C9B S2B C12B C11B -1.0(7) . . . . ?
C9B C8B C7B N3B -6.9(12) . . . . ?
C9B C8B C7B C6B -179.6(8) . . . . ?
C9B C10B C11B C12B -1.1(11) . . . . ?
C5B N2B C6B O1B -4.8(14) . . . . ?
C5B N2B C6B C7B 173.4(8) . . . . ?
C5B N1B C1B C2B -1.8(13) . . . . ?
C5B C4B C3B C2B 0.2(13) . . . . ?
C7B C8B C9B S2B 167.5(7) . . . . ?
C7B C8B C9B C10B -12.7(13) . . . . ?
C3B C4B C5B N2B 177.6(8) . . . . ?
C3B C4B C5B N1B -2.8(13) . . . . ?
C3B C2B C1B N1B -0.9(14) . . . . ?
C1B N1B C5B N2B -176.7(8) . . . . ?
C1B N1B C5B C4B 3.7(13) . . . . ?
C1B C2B C3B C4B 1.7(14) . . . . ?
C12B S2B C9B C8B -179.8(7) . . . . ?
C12B S2B C9B C10B 0.4(7) . . . . ?
C1A N1A C5A N2A 178.1(8) . . . . ?
C1A N1A C5A C4A -2.1(13) . . . . ?
C12A S2A C9A C8A -177.8(8) . . . . ?
C12A S2A C9A C10A -1.4(7) . . . . ?
C13A N3A C7A C8A 98.7(9) . . . . ?
C13A N3A C7A C6A -74.4(9) . . . . ?
C13B N3B C7B C6B 78.2(9) . . . . ?
C13B N3B C7B C8B -95.2(10) . . . . ?
_shelx_res_file
;
TITL xds_ascii_a.res in P2(1)2(1)2(1)
tnx.res
created by SHELXL-2017/1 at 19:18:07 on 18-Mar-2019
REM Old TITL XDS_ASCII in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1): R1 0.140, Rweak 0.037, Alpha 0.007
REM 2.096 for 29 systematic absences, Orientation as input
REM Flack x = 0.465 ( 0.036 ) from 2890 Parsons' quotients
REM Formula found by SHELXT: C31 N5 O8 S3 Cl13
CELL 0.7937 9.596 16.74 28.301 90 90 90
ZERR 8 0.0019 0.0033 0.0057 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Cl N O S
DISP C 0.005 0.002 14.692
DISP Cl 0.175 0.199 936.414
DISP H -0 0 0.628
DISP N 0.009 0.004 25.934
DISP O 0.015 0.008 43.791
DISP S 0.147 0.155 735.595
UNIT 120 104 48 24 32 16
EQIV $1 -1+X,+Y,+Z
EQIV $2 1+X,+Y,+Z
EQIV $3 2-X,-0.5+Y,1.5-Z
L.S. 10 0 0
PLAN 20
SIZE 0.03 0.03 0.1
TEMP -173.1(10)
HTAB N2B O2B
HTAB N2A O2A
HTAB N1B O1A_$1
HTAB N1B O1B
HTAB N1A O1A
HTAB N1A O1B_$2
HTAB C14B O2B
HTAB C14A O2A_$3
BOND
BOND $H
CONF
list 4
fmap 2 53
acta
REM
REM
REM
WGHT 0.087500 11.703600
FVAR 0.33146
S1B 6 1.059243 0.862442 0.912040 11.00000 0.03662 0.03418 =
0.02063 -0.00059 0.00026 0.00002
S1A 6 1.424772 0.702393 0.597460 11.00000 0.04407 0.03320 =
0.02125 -0.00333 -0.00164 0.00108
S2B 6 1.404649 0.708853 0.913720 11.00000 0.04013 0.03650 =
0.02894 0.00024 -0.00559 0.00227
CL3B 3 1.472935 0.586456 0.729993 11.00000 0.05606 0.04526 =
0.02884 -0.00200 -0.00374 0.00007
CL2B 3 1.535063 0.493013 0.814051 11.00000 0.05449 0.03170 =
0.04250 0.00414 -0.00692 0.00151
S2A 6 1.059245 0.839385 0.607306 11.00000 0.04360 0.03981 =
0.02553 -0.00135 -0.00700 0.00500
CL5B 3 1.133581 0.612595 0.993010 11.00000 0.05132 0.03699 =
0.04740 0.00122 0.00714 0.00350
CL1B 3 1.629376 0.656812 0.806705 11.00000 0.05049 0.03584 =
0.04000 -0.00119 -0.00787 -0.00112
CL4B 3 1.200779 0.448495 1.011341 11.00000 0.07675 0.03961 =
0.06001 0.01152 0.01307 0.00810
CL6B 3 1.220171 0.509903 0.916245 11.00000 0.08025 0.05872 =
0.03832 -0.01257 0.00452 -0.01152
CL5A 3 0.828581 0.475680 1.011586 11.00000 0.05632 0.06056 =
0.06877 -0.01519 -0.02371 0.00414
CL3A 3 1.187165 0.466241 0.789461 11.00000 0.05359 0.09099 =
0.05905 -0.02360 0.00216 0.00446
CL1A 3 0.959128 0.468005 0.724414 11.00000 0.10333 0.09748 =
0.05910 0.03943 -0.03665 -0.05141
CL6A 3 0.561305 0.399479 1.003454 11.00000 0.06254 0.14097 =
0.03845 0.00062 -0.00003 -0.03107
CL4A 3 0.635012 0.525780 0.938824 11.00000 0.08207 0.09444 =
0.04458 -0.00322 -0.01697 0.00437
CL2A 3 0.935015 0.540400 0.818178 11.00000 0.08717 0.06789 =
0.10584 0.01710 0.03706 0.02954
O3B 5 1.105008 0.929103 0.884286 11.00000 0.04429 0.03108 =
0.02574 0.00210 0.00182 0.00052
O2A 5 1.203035 0.837150 0.701804 11.00000 0.03900 0.04057 =
0.02233 -0.00473 -0.00039 0.00345
O1A 5 1.629651 0.791437 0.719110 11.00000 0.03783 0.03760 =
0.02295 -0.00308 -0.00149 0.00280
O1B 5 0.861406 0.775639 0.788627 11.00000 0.03628 0.04622 =
0.02515 -0.00560 -0.00303 0.00663
O4A 5 1.505594 0.695561 0.555166 11.00000 0.04709 0.04816 =
0.01989 -0.00640 0.00074 0.00508
O4B 5 0.974625 0.877297 0.952778 11.00000 0.03879 0.04473 =
0.02206 -0.00352 0.00382 -0.00356
O3A 5 1.390055 0.631409 0.622957 11.00000 0.04919 0.02764 =
0.02786 -0.00173 -0.00206 0.00047
O2B 5 1.270920 0.702724 0.817619 11.00000 0.03955 0.04232 =
0.02604 -0.00306 -0.00313 0.00496
N2B 4 1.059067 0.712702 0.761591 11.00000 0.03110 0.04065 =
0.02423 -0.00502 -0.00037 0.00096
AFIX 43
H2B 2 1.147010 0.702248 0.767872 11.00000 -1.20000
AFIX 0
N3A 4 1.503493 0.762946 0.633329 11.00000 0.03304 0.03644 =
0.02246 -0.00097 0.00274 0.00106
N2A 4 1.426226 0.833394 0.753250 11.00000 0.03340 0.03642 =
0.02079 -0.00367 -0.00373 -0.00339
AFIX 43
H2A 2 1.334901 0.831050 0.750785 11.00000 -1.20000
AFIX 0
N3B 4 0.978163 0.800308 0.877236 11.00000 0.03694 0.03519 =
0.02349 0.00062 0.00514 -0.00162
N1B 4 0.875925 0.700705 0.706938 11.00000 0.03610 0.03868 =
0.02395 -0.00627 -0.00480 0.00551
AFIX 43
H1B 2 0.823979 0.728597 0.726546 11.00000 -1.20000
AFIX 0
N1A 4 1.615978 0.862702 0.802407 11.00000 0.04032 0.03127 =
0.02311 -0.00365 -0.00210 0.00177
AFIX 43
H1A 2 1.669879 0.837497 0.782144 11.00000 -1.20000
AFIX 0
C8A 1 1.283496 0.810644 0.668974 11.00000 0.03948 0.02601 =
0.02307 -0.00384 -0.00083 0.00174
C6A 1 1.501966 0.803115 0.715710 11.00000 0.03317 0.02842 =
0.02149 0.00018 0.00099 0.00351
C6B 1 0.984325 0.753690 0.796051 11.00000 0.03855 0.04086 =
0.02341 -0.00170 -0.00011 -0.00167
C7A 1 1.421812 0.790412 0.673426 11.00000 0.03589 0.03286 =
0.02080 -0.00123 0.00471 0.00170
C5A 1 1.478081 0.866664 0.793885 11.00000 0.03528 0.03163 =
0.02014 -0.00253 -0.00372 0.00102
C4A 1 1.392324 0.904071 0.826515 11.00000 0.03517 0.03792 =
0.02664 -0.00315 0.00332 0.00278
AFIX 43
H4A 2 1.294344 0.906203 0.821878 11.00000 -1.20000
AFIX 0
C4B 1 1.094285 0.647095 0.686907 11.00000 0.03773 0.03471 =
0.02749 -0.00101 0.00051 -0.00097
AFIX 43
H4B 2 1.190003 0.638808 0.693938 11.00000 -1.20000
AFIX 0
C2B 1 0.897873 0.632105 0.634705 11.00000 0.03937 0.03909 =
0.02777 -0.00433 0.00010 0.00297
AFIX 43
H2BA 2 0.858859 0.611973 0.606245 11.00000 -1.20000
AFIX 0
C8B 1 1.194378 0.737293 0.847176 11.00000 0.03131 0.03932 =
0.02359 0.00376 0.00402 0.00399
C10B 1 1.204805 0.805670 0.927866 11.00000 0.04023 0.03217 =
0.02315 0.00211 0.00074 -0.00594
C10A 1 1.271090 0.752471 0.585181 11.00000 0.04052 0.03270 =
0.02412 -0.00264 -0.00032 -0.00085
C9A 1 1.219414 0.799163 0.621936 11.00000 0.04040 0.03621 =
0.02094 -0.00359 0.00093 -0.00294
C11B 1 1.286397 0.809677 0.969445 11.00000 0.04442 0.03124 =
0.02506 0.00005 -0.00511 -0.00640
AFIX 43
H11B 2 1.266877 0.843063 0.995770 11.00000 -1.20000
AFIX 0
C11A 1 1.182266 0.752835 0.545462 11.00000 0.04399 0.03679 =
0.02411 -0.00298 -0.00636 0.00486
AFIX 43
H11A 2 1.202738 0.725562 0.516855 11.00000 -1.20000
AFIX 0
C9B 1 1.255534 0.754515 0.894904 11.00000 0.03521 0.03330 =
0.02518 -0.00061 -0.00485 -0.00167
C5B 1 1.008851 0.686832 0.718535 11.00000 0.04021 0.03716 =
0.02271 0.00359 -0.00331 -0.00101
C7B 1 1.060349 0.765002 0.839567 11.00000 0.03031 0.03304 =
0.02605 -0.00336 0.00047 0.00328
C3A 1 1.453200 0.938341 0.866140 11.00000 0.04705 0.03504 =
0.02046 -0.00553 -0.00116 0.00032
AFIX 43
H3A 2 1.395172 0.964196 0.888630 11.00000 -1.20000
AFIX 0
C3B 1 1.038181 0.619602 0.644872 11.00000 0.04112 0.03405 =
0.03146 -0.00150 0.00776 0.00144
AFIX 43
H3B 2 1.095601 0.592112 0.622887 11.00000 -1.20000
AFIX 0
C1B 1 0.816883 0.673373 0.665807 11.00000 0.04200 0.04078 =
0.02247 -0.00186 -0.00412 0.00492
AFIX 43
H1BA 2 0.721326 0.683060 0.659161 11.00000 -1.20000
AFIX 0
C14B 1 1.496281 0.589513 0.792413 11.00000 0.04621 0.04226 =
0.02421 -0.00102 0.00165 0.00834
AFIX 13
H14B 2 1.407670 0.608307 0.807319 11.00000 -1.20000
AFIX 0
C12B 1 1.396580 0.759020 0.966376 11.00000 0.04990 0.03519 =
0.02603 0.00016 -0.00949 -0.00391
AFIX 43
H12B 2 1.462690 0.752098 0.991024 11.00000 -1.20000
AFIX 0
C1A 1 1.674112 0.896203 0.841078 11.00000 0.03741 0.04243 =
0.02934 -0.00844 -0.00608 0.00253
AFIX 43
H1AA 2 1.771899 0.892186 0.845745 11.00000 -1.20000
AFIX 0
C2A 1 1.593973 0.936155 0.873920 11.00000 0.04198 0.03977 =
0.02505 -0.00673 -0.00551 0.00210
AFIX 43
H2AA 2 1.634649 0.961050 0.900748 11.00000 -1.20000
AFIX 0
C12A 1 1.064724 0.796129 0.552362 11.00000 0.04897 0.04066 =
0.02635 -0.00109 -0.00804 0.00367
AFIX 43
H12A 2 0.993329 0.801895 0.529358 11.00000 -1.20000
AFIX 0
C13A 1 1.591898 0.826874 0.611168 11.00000 0.04937 0.03605 =
0.02353 0.00459 0.00608 -0.00005
AFIX 137
H13D 2 1.640236 0.804954 0.583557 11.00000 -1.50000
H13E 2 1.660596 0.845874 0.634194 11.00000 -1.50000
H13F 2 1.532514 0.871485 0.601300 11.00000 -1.50000
AFIX 0
C13B 1 0.882103 0.742092 0.901232 11.00000 0.03952 0.04480 =
0.02712 -0.00193 0.00319 -0.00844
AFIX 137
H13A 2 0.937076 0.699342 0.915801 11.00000 -1.50000
H13B 2 0.818259 0.719091 0.877879 11.00000 -1.50000
H13C 2 0.828364 0.769898 0.925657 11.00000 -1.50000
AFIX 0
C14A 1 1.008283 0.464161 0.784811 11.00000 0.06133 0.04737 =
0.04770 0.01335 -0.00267 -0.02181
AFIX 13
H14A 2 0.975020 0.412149 0.798033 11.00000 -1.20000
AFIX 0
C15B 1 1.241208 0.532845 0.976474 11.00000 0.04385 0.03959 =
0.03873 0.00073 0.00296 -0.00195
AFIX 13
H15B 2 1.340502 0.548144 0.982230 11.00000 -1.20000
AFIX 0
PART 2
C15A 1 0.698837 0.450729 0.971757 10.50000 0.03217 0.03849 =
0.03654 -0.00731 -0.00112 0.00359
AFIX 13
H15A 2 0.740114 0.411090 0.949332 10.50000 -1.20000
AFIX 0
PART 0
PART 1
C1 1 0.652354 0.477497 0.998878 10.50000 0.07147 0.06584 =
0.03980 -0.01340 0.01412 -0.01541
AFIX 13
H1 2 0.610874 0.516447 1.021680 10.50000 -1.20000
AFIX 0
HKLF 4
REM xds_ascii_a.res in P2(1)2(1)2(1)
REM R1 = 0.0636 for 7832 Fo > 4sig(Fo) and 0.0869 for all 10006 data
REM 552 parameters refined using 0 restraints
END
WGHT 0.0817 11.8169
REM Highest difference peak 1.216, deepest hole -0.889, 1-sigma level 0.118
Q1 1 0.8793 0.5045 0.7401 11.00000 0.05 1.22
Q2 1 1.1476 0.4158 0.7997 11.00000 0.05 0.68
Q3 1 1.7448 0.6180 0.8198 11.00000 0.05 0.46
Q4 1 1.4909 0.7709 0.9034 11.00000 0.05 0.43
Q5 1 1.4114 0.9125 0.5955 11.00000 0.05 0.43
Q6 1 1.2773 0.6990 0.5830 11.00000 0.05 0.42
Q7 1 1.5093 0.6388 0.5965 11.00000 0.05 0.41
Q8 1 1.5588 0.6644 0.8410 11.00000 0.05 0.41
Q9 1 1.6289 0.5609 0.8005 11.00000 0.05 0.41
Q10 1 1.1488 0.4823 0.7608 11.00000 0.05 0.41
Q11 1 1.3460 0.4589 0.9181 11.00000 0.05 0.40
Q12 1 1.3958 0.5201 0.8022 11.00000 0.05 0.39
Q13 1 1.3896 0.4970 0.8155 11.00000 0.05 0.39
Q14 1 1.3804 0.4988 0.9195 11.00000 0.05 0.39
Q15 1 0.9122 0.8795 0.9139 11.00000 0.05 0.39
Q16 1 0.9026 0.4059 0.8010 11.00000 0.05 0.38
Q17 1 1.5954 0.6282 0.5639 11.00000 0.05 0.38
Q18 1 0.9767 0.7827 0.5942 11.00000 0.05 0.37
Q19 1 0.9356 0.5255 1.0007 11.00000 0.05 0.37
Q20 1 0.7351 0.6399 0.8967 11.00000 0.05 0.37
;
_shelx_res_checksum 60541
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform under -18 ?'
_chemical_properties_physical Heat-sensitive
#######################################################################
#
# 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_tnx_acetonitrile
_database_code_depnum_ccdc_archive 'CCDC 1904101'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record
;
2019-07-04 deposited with the CCDC. 2019-07-12 downloaded from the CCDC.
;
_audit_creation_date 2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common 'tenoxicam acetonitrile solvat'
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H11 N3 O4 S2, C2 H3 N'
_chemical_formula_sum 'C15 H14 N4 O4 S2'
_chemical_formula_weight 378.42
_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/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 9.1718(3)
_cell_length_b 8.9965(3)
_cell_length_c 21.1092(8)
_cell_angle_alpha 90
_cell_angle_beta 98.591(4)
_cell_angle_gamma 90
_cell_volume 1722.26(11)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 6671
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 26.1550
_cell_measurement_theta_min 3.7050
_shelx_estimated_absorpt_T_max 0.997
_shelx_estimated_absorpt_T_min 0.957
_exptl_absorpt_coefficient_mu 0.338
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.82253
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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 1.459
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 784
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max 0.13
_exptl_crystal_size_mid 0.07
_exptl_crystal_size_min 0.01
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0603
_diffrn_reflns_av_unetI/netI 0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_number 26375
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.365
_diffrn_reflns_theta_min 3.190
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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 -70.00 2.00 1.00 90.00 -- -11.27 127.00-122.49 72
2 \w -74.00 -2.00 1.00 90.00 -- -11.27 133.00 -23.53 72
3 \w -67.00 -5.00 1.00 90.00 -- -11.27 122.00 98.73 62
4 \w -90.00 -28.00 1.00 90.00 -- -11.27 -77.00-150.00 62
5 \w -85.00 16.00 1.00 90.00 -- -11.27 -57.00 90.00 101
6 \w -87.00 13.00 1.00 90.00 -- -11.27 -38.00-120.00 100
7 \w -74.00 48.00 1.00 90.00 -- -11.27 0.00 -60.00 122
8 \w -77.00 -45.00 1.00 90.00 -- 11.43 178.00-150.00 32
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0755395000
_diffrn_orient_matrix_UB_12 0.0150364000
_diffrn_orient_matrix_UB_13 -0.0010261000
_diffrn_orient_matrix_UB_21 0.0114499000
_diffrn_orient_matrix_UB_22 0.0127030000
_diffrn_orient_matrix_UB_23 0.0335194000
_diffrn_orient_matrix_UB_31 0.0168119000
_diffrn_orient_matrix_UB_32 -0.0763684000
_diffrn_orient_matrix_UB_33 0.0053893000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_diffrn_special_details ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2809
_reflns_number_total 3527
_reflns_odcompleteness_completeness 99.74
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.43d (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 'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max 0.284
_refine_diff_density_min -0.263
_refine_diff_density_rms 0.044
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.058
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 228
_refine_ls_number_reflns 3527
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0613
_refine_ls_R_factor_gt 0.0434
_refine_ls_restrained_S_all 1.058
_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^)+(0.0413P)^2^+0.5668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0934
_refine_ls_wR_factor_ref 0.1011
_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 Aromatic/amide H refined with riding coordinates:
N1(H1), N2(H2), C4(H4), C2(H2A), C1(H1A), C11(H11), C3(H3), C12(H12)
2.b Idealised Me refined as rotating group:
C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens geom
_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 0.26080(6) 0.15844(6) 0.66918(2) 0.03739(16) Uani 1 1 d . . . . .
S2 S -0.15771(6) 0.00952(7) 0.58450(3) 0.04344(17) Uani 1 1 d . . . . .
O2 O -0.05353(15) 0.25012(17) 0.49995(7) 0.0444(4) Uani 1 1 d . . . . .
O1 O 0.38693(16) 0.39632(18) 0.51737(7) 0.0483(4) Uani 1 1 d . . . . .
O3 O 0.23540(17) 0.30263(18) 0.69419(7) 0.0494(4) Uani 1 1 d . . . . .
O4 O 0.36648(17) 0.0632(2) 0.70598(8) 0.0569(5) Uani 1 1 d . . . . .
N1 N 0.31803(18) 0.56170(18) 0.41385(8) 0.0350(4) Uani 1 1 d . . . . .
H1 H 0.382351 0.545439 0.447148 0.042 Uiso 1 1 calc R . . . .
N3 N 0.30769(18) 0.18048(19) 0.59807(8) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.15581(19) 0.4041(2) 0.45818(8) 0.0394(4) Uani 1 1 d . . . . .
H2 H 0.066367 0.373544 0.456137 0.047 Uiso 1 1 calc R . . . .
C5 C 0.1854(2) 0.4966(2) 0.41028(9) 0.0334(5) Uani 1 1 d . . . . .
C7 C 0.1965(2) 0.2504(2) 0.55090(9) 0.0325(5) Uani 1 1 d . . . . .
C8 C 0.0479(2) 0.2057(2) 0.54358(9) 0.0328(5) Uani 1 1 d . . . . .
C6 C 0.2562(2) 0.3543(2) 0.50995(10) 0.0353(5) Uani 1 1 d . . . . .
C10 C 0.0912(2) 0.0671(2) 0.65065(10) 0.0354(5) Uani 1 1 d . . . . .
C9 C 0.0078(2) 0.1019(2) 0.59272(10) 0.0327(5) Uani 1 1 d . . . . .
C4 C 0.0817(2) 0.5250(3) 0.35618(11) 0.0440(6) Uani 1 1 d . . . . .
H4 H -0.011260 0.481679 0.352329 0.053 Uiso 1 1 calc R . . . .
C2 C 0.2558(2) 0.6813(3) 0.31455(10) 0.0418(5) Uani 1 1 d . . . . .
H2A H 0.280208 0.743811 0.282656 0.050 Uiso 1 1 calc R . . . .
C1 C 0.3552(2) 0.6516(2) 0.36755(10) 0.0397(5) Uani 1 1 d . . . . .
H1A H 0.448899 0.693361 0.371932 0.048 Uiso 1 1 calc R . . . .
C11 C 0.0231(3) -0.0351(3) 0.68807(11) 0.0479(6) Uani 1 1 d . . . . .
H11 H 0.065247 -0.069965 0.728114 0.057 Uiso 1 1 calc R . . . .
C3 C 0.1164(3) 0.6161(3) 0.30895(11) 0.0465(6) Uani 1 1 d . . . . .
H3 H 0.047032 0.634738 0.272985 0.056 Uiso 1 1 calc R . . . .
C13 C 0.3864(3) 0.0557(3) 0.57243(12) 0.0518(6) Uani 1 1 d . . . . .
H13A H 0.463946 0.021483 0.604759 0.078 Uiso 1 1 calc GR . . . .
H13B H 0.427731 0.088782 0.535696 0.078 Uiso 1 1 calc GR . . . .
H13C H 0.318489 -0.024091 0.560205 0.078 Uiso 1 1 calc GR . . . .
C12 C -0.1124(3) -0.0752(3) 0.65747(12) 0.0528(6) Uani 1 1 d . . . . .
H12 H -0.173970 -0.141691 0.674400 0.063 Uiso 1 1 calc R . . . .
C14 C 0.5451(3) 0.3041(3) 0.35379(14) 0.0570(7) Uani 1 1 d . . . . .
N4 N 0.4237(3) 0.2770(3) 0.34459(15) 0.0906(9) Uani 1 1 d . . . . .
C15 C 0.7008(3) 0.3389(3) 0.36419(16) 0.0741(9) Uani 1 1 d . . . . .
H15A H 0.749285 0.284238 0.334309 0.111 Uiso 1 1 calc GR . . . .
H15B H 0.742395 0.312048 0.407115 0.111 Uiso 1 1 calc GR . . . .
H15C H 0.713980 0.443491 0.358068 0.111 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 0.0312(3) 0.0479(3) 0.0300(3) 0.0069(2) -0.0056(2) -0.0050(2)
S2 0.0348(3) 0.0544(4) 0.0397(3) -0.0029(3) 0.0010(2) -0.0137(3)
O2 0.0311(8) 0.0609(10) 0.0379(8) 0.0132(7) -0.0058(7) -0.0020(7)
O1 0.0314(8) 0.0651(10) 0.0442(9) 0.0199(8) -0.0083(7) -0.0119(7)
O3 0.0494(10) 0.0561(10) 0.0397(9) -0.0120(8) -0.0033(7) -0.0102(8)
O4 0.0418(9) 0.0757(12) 0.0483(10) 0.0290(9) -0.0091(8) 0.0011(8)
N1 0.0298(9) 0.0429(10) 0.0297(9) 0.0045(8) -0.0036(7) -0.0023(8)
N3 0.0268(9) 0.0411(10) 0.0326(9) 0.0085(8) -0.0023(7) 0.0006(7)
N2 0.0276(9) 0.0508(11) 0.0369(10) 0.0136(9) -0.0039(8) -0.0055(8)
C5 0.0296(11) 0.0368(11) 0.0324(11) 0.0034(9) 0.0003(9) 0.0012(9)
C7 0.0281(11) 0.0389(11) 0.0282(10) 0.0043(9) -0.0034(8) -0.0006(9)
C8 0.0314(11) 0.0369(11) 0.0284(10) -0.0004(9) -0.0008(9) 0.0000(9)
C6 0.0316(12) 0.0413(12) 0.0308(11) 0.0038(9) -0.0021(9) -0.0007(9)
C10 0.0324(11) 0.0397(12) 0.0325(11) 0.0030(9) -0.0001(9) -0.0032(9)
C9 0.0279(11) 0.0361(11) 0.0332(11) -0.0022(9) 0.0013(8) -0.0042(8)
C4 0.0300(12) 0.0575(14) 0.0412(13) 0.0095(11) -0.0053(10) -0.0057(10)
C2 0.0433(13) 0.0482(13) 0.0335(12) 0.0094(10) 0.0048(10) 0.0000(10)
C1 0.0368(12) 0.0447(13) 0.0370(12) 0.0057(10) 0.0036(10) -0.0066(10)
C11 0.0482(14) 0.0535(14) 0.0411(13) 0.0132(11) 0.0038(11) -0.0062(11)
C3 0.0434(14) 0.0585(15) 0.0339(12) 0.0108(11) -0.0058(10) 0.0021(11)
C13 0.0480(15) 0.0561(15) 0.0506(15) 0.0047(12) 0.0052(12) 0.0139(12)
C12 0.0539(16) 0.0544(15) 0.0509(15) 0.0100(12) 0.0104(12) -0.0170(12)
C14 0.0567(18) 0.0443(14) 0.0687(18) -0.0103(13) 0.0052(14) -0.0001(12)
N4 0.0560(17) 0.0792(18) 0.135(3) -0.0366(17) 0.0092(17) -0.0079(14)
C15 0.0570(19) 0.0717(19) 0.091(2) 0.0043(17) 0.0038(16) -0.0093(15)
_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 1.4327(17) . ?
S1 O4 1.4324(16) . ?
S1 N3 1.6341(18) . ?
S1 C10 1.751(2) . ?
S2 C9 1.717(2) . ?
S2 C12 1.713(3) . ?
O2 C8 1.272(2) . ?
O1 C6 1.244(2) . ?
N1 H1 0.8600 . ?
N1 C5 1.342(3) . ?
N1 C1 1.351(3) . ?
N3 C7 1.457(2) . ?
N3 C13 1.480(3) . ?
N2 H2 0.8600 . ?
N2 C5 1.368(3) . ?
N2 C6 1.394(3) . ?
C5 C4 1.396(3) . ?
C7 C8 1.408(3) . ?
C7 C6 1.436(3) . ?
C8 C9 1.482(3) . ?
C10 C9 1.378(3) . ?
C10 C11 1.416(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.364(3) . ?
C2 H2A 0.9300 . ?
C2 C1 1.360(3) . ?
C2 C3 1.396(3) . ?
C1 H1A 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.361(3) . ?
C3 H3 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12 0.9300 . ?
C14 N4 1.129(3) . ?
C14 C15 1.446(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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 N3 107.96(9) . . ?
O3 S1 C10 108.62(10) . . ?
O4 S1 O3 118.41(10) . . ?
O4 S1 N3 108.73(10) . . ?
O4 S1 C10 110.31(10) . . ?
N3 S1 C10 101.46(9) . . ?
C12 S2 C9 91.86(11) . . ?
C5 N1 H1 118.5 . . ?
C5 N1 C1 123.03(17) . . ?
C1 N1 H1 118.5 . . ?
C7 N3 S1 115.27(14) . . ?
C7 N3 C13 114.01(17) . . ?
C13 N3 S1 116.97(14) . . ?
C5 N2 H2 116.8 . . ?
C5 N2 C6 126.46(17) . . ?
C6 N2 H2 116.8 . . ?
N1 C5 N2 120.16(17) . . ?
N1 C5 C4 117.84(18) . . ?
N2 C5 C4 122.00(19) . . ?
C8 C7 N3 121.27(17) . . ?
C8 C7 C6 124.74(18) . . ?
C6 C7 N3 113.69(17) . . ?
O2 C8 C7 125.54(19) . . ?
O2 C8 C9 118.27(18) . . ?
C7 C8 C9 116.15(17) . . ?
O1 C6 N2 120.84(19) . . ?
O1 C6 C7 124.64(18) . . ?
N2 C6 C7 114.48(18) . . ?
C9 C10 S1 116.63(15) . . ?
C9 C10 C11 114.20(19) . . ?
C11 C10 S1 129.11(16) . . ?
C8 C9 S2 122.86(15) . . ?
C10 C9 S2 110.16(15) . . ?
C10 C9 C8 126.97(18) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C1 C2 H2A 120.7 . . ?
C1 C2 C3 118.7(2) . . ?
C3 C2 H2A 120.7 . . ?
N1 C1 C2 120.2(2) . . ?
N1 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C10 C11 H11 124.6 . . ?
C12 C11 C10 110.8(2) . . ?
C12 C11 H11 124.6 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S2 C12 H12 123.5 . . ?
C11 C12 S2 112.98(18) . . ?
C11 C12 H12 123.5 . . ?
N4 C14 C15 178.8(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
_geom_hbond_publ_flag
N1 H1 O1 0.86 2.00 2.641(2) 131.1 . yes
N1 H1 O1 0.86 2.20 2.898(2) 138.2 3_666 yes
N2 H2 O2 0.86 1.90 2.624(2) 141.3 . yes
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 N3 C7 C8 -45.8(2) . . . . ?
S1 N3 C7 C6 140.23(16) . . . . ?
S1 C10 C9 S2 -176.98(11) . . . . ?
S1 C10 C9 C8 1.7(3) . . . . ?
S1 C10 C11 C12 177.01(19) . . . . ?
O2 C8 C9 S2 14.0(3) . . . . ?
O2 C8 C9 C10 -164.5(2) . . . . ?
O3 S1 N3 C7 -61.83(16) . . . . ?
O3 S1 N3 C13 160.00(16) . . . . ?
O3 S1 C10 C9 81.77(18) . . . . ?
O3 S1 C10 C11 -95.5(2) . . . . ?
O4 S1 N3 C7 168.53(14) . . . . ?
O4 S1 N3 C13 30.36(18) . . . . ?
O4 S1 C10 C9 -146.94(17) . . . . ?
O4 S1 C10 C11 35.8(2) . . . . ?
N1 C5 C4 C3 0.1(3) . . . . ?
N3 S1 C10 C9 -31.82(19) . . . . ?
N3 S1 C10 C11 150.9(2) . . . . ?
N3 C7 C8 O2 -172.98(19) . . . . ?
N3 C7 C8 C9 9.2(3) . . . . ?
N3 C7 C6 O1 -8.0(3) . . . . ?
N3 C7 C6 N2 170.09(18) . . . . ?
N2 C5 C4 C3 -178.9(2) . . . . ?
C5 N1 C1 C2 0.8(3) . . . . ?
C5 N2 C6 O1 1.9(3) . . . . ?
C5 N2 C6 C7 -176.30(19) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?
C7 C8 C9 S2 -168.03(16) . . . . ?
C7 C8 C9 C10 13.4(3) . . . . ?
C8 C7 C6 O1 178.3(2) . . . . ?
C8 C7 C6 N2 -3.7(3) . . . . ?
C6 N2 C5 N1 -7.3(3) . . . . ?
C6 N2 C5 C4 171.7(2) . . . . ?
C6 C7 C8 O2 0.3(3) . . . . ?
C6 C7 C8 C9 -177.50(19) . . . . ?
C10 S1 N3 C7 52.26(16) . . . . ?
C10 S1 N3 C13 -85.91(17) . . . . ?
C10 C11 C12 S2 -0.2(3) . . . . ?
C9 S2 C12 C11 0.5(2) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C1 N1 C5 N2 178.57(19) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C11 C10 C9 S2 0.7(2) . . . . ?
C11 C10 C9 C8 179.4(2) . . . . ?
C3 C2 C1 N1 -0.6(3) . . . . ?
C13 N3 C7 C8 93.6(2) . . . . ?
C13 N3 C7 C6 -80.4(2) . . . . ?
C12 S2 C9 C8 -179.44(19) . . . . ?
C12 S2 C9 C10 -0.69(18) . . . . ?
_shelx_res_file
;
TITL
tnxacetonitrile.res
created by SHELXL-2017/1 at 12:22:28 on 01-Jul-2019
CELL 0.71073 9.1718 8.9965 21.1092 90 98.591 90
ZERR 4 0.0003 0.0003 0.0008 0 0.004 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 60 56 16 16 8
EQIV $1 1-X,1-Y,1-Z
L.S. 10
PLAN 20
SIZE 0.01 0.07 0.13
TEMP 20(2)
HTAB N1 O1
HTAB N1 O1_$1
HTAB N2 O2
fmap 2 53
acta
BOND
BOND $H
CONF
SHEL 40 0.8
REM
REM
REM
WGHT 0.041300 0.566800
FVAR 0.46391
S1 5 0.260800 0.158440 0.669179 11.00000 0.03115 0.04793 =
0.02997 0.00693 -0.00563 -0.00498
S2 5 -0.157711 0.009524 0.584504 11.00000 0.03480 0.05439 =
0.03973 -0.00294 0.00101 -0.01374
O2 4 -0.053526 0.250120 0.499947 11.00000 0.03105 0.06093 =
0.03791 0.01318 -0.00575 -0.00202
O1 4 0.386925 0.396321 0.517370 11.00000 0.03136 0.06508 =
0.04416 0.01991 -0.00832 -0.01191
O3 4 0.235395 0.302627 0.694194 11.00000 0.04938 0.05615 =
0.03973 -0.01198 -0.00329 -0.01017
O4 4 0.366481 0.063222 0.705982 11.00000 0.04182 0.07566 =
0.04833 0.02899 -0.00912 0.00112
N1 3 0.318033 0.561704 0.413850 11.00000 0.02982 0.04293 =
0.02971 0.00451 -0.00362 -0.00233
AFIX 43
H1 2 0.382351 0.545439 0.447148 11.00000 -1.20000
AFIX 0
N3 3 0.307691 0.180476 0.598070 11.00000 0.02675 0.04107 =
0.03258 0.00853 -0.00226 0.00059
N2 3 0.155807 0.404060 0.458175 11.00000 0.02763 0.05083 =
0.03694 0.01358 -0.00388 -0.00555
AFIX 43
H2 2 0.066367 0.373544 0.456137 11.00000 -1.20000
AFIX 0
C5 1 0.185405 0.496576 0.410277 11.00000 0.02958 0.03682 =
0.03245 0.00342 0.00029 0.00121
C7 1 0.196547 0.250353 0.550898 11.00000 0.02810 0.03891 =
0.02820 0.00428 -0.00335 -0.00060
C8 1 0.047905 0.205666 0.543583 11.00000 0.03137 0.03694 =
0.02842 -0.00043 -0.00079 -0.00001
C6 1 0.256214 0.354347 0.509953 11.00000 0.03164 0.04130 =
0.03083 0.00377 -0.00214 -0.00074
C10 1 0.091185 0.067102 0.650647 11.00000 0.03243 0.03973 =
0.03254 0.00297 -0.00012 -0.00322
C9 1 0.007792 0.101941 0.592720 11.00000 0.02787 0.03612 =
0.03317 -0.00220 0.00133 -0.00416
C4 1 0.081717 0.524984 0.356180 11.00000 0.02998 0.05747 =
0.04125 0.00948 -0.00534 -0.00570
AFIX 43
H4 2 -0.011260 0.481679 0.352329 11.00000 -1.20000
AFIX 0
C2 1 0.255769 0.681294 0.314548 11.00000 0.04329 0.04816 =
0.03352 0.00937 0.00476 0.00003
AFIX 43
H2A 2 0.280208 0.743811 0.282656 11.00000 -1.20000
AFIX 0
C1 1 0.355157 0.651640 0.367547 11.00000 0.03679 0.04472 =
0.03700 0.00573 0.00356 -0.00659
AFIX 43
H1A 2 0.448899 0.693361 0.371932 11.00000 -1.20000
AFIX 0
C11 1 0.023097 -0.035060 0.688072 11.00000 0.04816 0.05348 =
0.04112 0.01322 0.00381 -0.00615
AFIX 43
H11 2 0.065247 -0.069965 0.728114 11.00000 -1.20000
AFIX 0
C3 1 0.116379 0.616079 0.308952 11.00000 0.04343 0.05853 =
0.03390 0.01079 -0.00584 0.00213
AFIX 43
H3 2 0.047032 0.634738 0.272985 11.00000 -1.20000
AFIX 0
C13 1 0.386376 0.055702 0.572430 11.00000 0.04805 0.05609 =
0.05064 0.00465 0.00519 0.01394
AFIX 137
H13A 2 0.463946 0.021483 0.604759 11.00000 -1.50000
H13B 2 0.427731 0.088782 0.535696 11.00000 -1.50000
H13C 2 0.318489 -0.024091 0.560205 11.00000 -1.50000
AFIX 0
C12 1 -0.112396 -0.075195 0.657466 11.00000 0.05388 0.05435 =
0.05093 0.01000 0.01042 -0.01699
AFIX 43
H12 2 -0.173970 -0.141691 0.674400 11.00000 -1.20000
AFIX 0
C14 1 0.545125 0.304102 0.353789 11.00000 0.05674 0.04429 =
0.06870 -0.01031 0.00521 -0.00007
N4 3 0.423661 0.277010 0.344593 11.00000 0.05604 0.07917 =
0.13507 -0.03660 0.00922 -0.00793
C15 1 0.700772 0.338893 0.364194 11.00000 0.05704 0.07171 =
0.09118 0.00427 0.00379 -0.00933
AFIX 137
H15A 2 0.749285 0.284238 0.334309 11.00000 -1.50000
H15B 2 0.742395 0.312048 0.407115 11.00000 -1.50000
H15C 2 0.713980 0.443491 0.358068 11.00000 -1.50000
AFIX 0
HKLF 4
REM
REM R1 = 0.0434 for 2809 Fo > 4sig(Fo) and 0.0613 for all 3527 data
REM 228 parameters refined using 0 restraints
END
WGHT 0.0412 0.5666
REM Highest difference peak 0.284, deepest hole -0.263, 1-sigma level 0.044
Q1 1 0.1599 0.1134 0.6621 11.00000 0.05 0.28
Q2 1 -0.0599 0.0530 0.5860 11.00000 0.05 0.26
Q3 1 0.4278 0.2615 0.3972 11.00000 0.05 0.25
Q4 1 0.2531 0.2205 0.5798 11.00000 0.05 0.20
Q5 1 0.3130 0.0418 0.6792 11.00000 0.05 0.17
Q6 1 0.2276 0.2799 0.5263 11.00000 0.05 0.17
Q7 1 0.3650 0.2322 0.6127 11.00000 0.05 0.17
Q8 1 0.1199 0.2669 0.5592 11.00000 0.05 0.16
Q9 1 0.7590 0.2539 0.3842 11.00000 0.05 0.16
Q10 1 0.1034 0.5711 0.3960 11.00000 0.05 0.16
Q11 1 0.0760 0.0204 0.6732 11.00000 0.05 0.16
Q12 1 0.0596 0.0624 0.6153 11.00000 0.05 0.15
Q13 1 0.1453 0.2025 0.5292 11.00000 0.05 0.15
Q14 1 -0.2699 0.0277 0.5724 11.00000 0.05 0.15
Q15 1 0.4329 0.4394 0.4789 11.00000 0.05 0.15
Q16 1 0.2965 0.1191 0.6138 11.00000 0.05 0.14
Q17 1 0.1705 0.6749 0.3228 11.00000 0.05 0.14
Q18 1 -0.0573 -0.0162 0.6792 11.00000 0.05 0.14
Q19 1 0.1949 0.3442 0.5596 11.00000 0.05 0.14
Q20 1 0.4262 0.3085 0.3373 11.00000 0.05 0.13
;
_shelx_res_checksum 62913
_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 1.152
_oxdiff_exptl_absorpt_empirical_full_min 0.910
#######################################################################
#
# 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_tnx_dmfa
_database_code_depnum_ccdc_archive 'CCDC 1538134'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record
;
2019-07-05 deposited with the CCDC. 2019-07-12 downloaded from the CCDC.
;
_audit_creation_date 2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common 'tenoxicam dimethylformamide solvate'
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H11 N3 O4 S2, C3 H7 N O'
_chemical_formula_sum 'C16 H18 N4 O5 S2'
_chemical_formula_weight 410.46
_chemical_melting_point ?
_chemical_oxdiff_formula 'C11 H10 N O'
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 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 9.1060(4)
_cell_length_b 9.4381(4)
_cell_length_c 11.6586(6)
_cell_angle_alpha 74.530(4)
_cell_angle_beta 77.500(4)
_cell_angle_gamma 85.545(3)
_cell_volume 942.56(8)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 3939
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.1190
_cell_measurement_theta_min 1.8380
_shelx_estimated_absorpt_T_max 0.956
_shelx_estimated_absorpt_T_min 0.870
_exptl_absorpt_coefficient_mu 0.318
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.82742
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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 1.446
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 428
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.144
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0342
_diffrn_reflns_av_unetI/netI 0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 11967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.369
_diffrn_reflns_theta_min 1.851
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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 -40.00 22.00 1.00 50.00 -- -23.36 -57.00 30.00 62
2 \w -43.00 68.00 1.00 50.00 -- -23.36 37.00-120.00 111
3 \w -31.00 28.00 1.00 50.00 -- 22.89 96.00 -51.00 59
4 \w 73.00 112.00 1.00 50.00 -- 22.89-178.00 -90.00 39
5 \w -44.00 76.00 1.00 50.00 -- -23.36 77.00 60.00 120
6 \w -80.00 29.00 1.00 50.00 -- -23.36 -37.00 120.00 109
7 \w -77.00 29.00 1.00 50.00 -- -23.36 96.00 -51.00 106
8 \w -122.00 -84.00 1.00 50.00 -- -23.36 -37.00 120.00 38
9 \w -127.00 5.00 1.00 50.00 -- -23.36 -57.00 -30.00 132
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0534944000
_diffrn_orient_matrix_UB_12 -0.0562865000
_diffrn_orient_matrix_UB_13 0.0167089000
_diffrn_orient_matrix_UB_21 -0.0111266000
_diffrn_orient_matrix_UB_22 0.0139338000
_diffrn_orient_matrix_UB_23 0.0581610000
_diffrn_orient_matrix_UB_31 -0.0581645000
_diffrn_orient_matrix_UB_32 -0.0521634000
_diffrn_orient_matrix_UB_33 0.0222609000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2958
_reflns_number_total 3857
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 0.253
_refine_diff_density_min -0.305
_refine_diff_density_rms 0.042
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 257
_refine_ls_number_reflns 3857
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0585
_refine_ls_R_factor_gt 0.0427
_refine_ls_restrained_S_all 1.040
_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^)+(0.0586P)^2^+0.1452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1110
_refine_ls_wR_factor_ref 0.1227
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Others
Sof(H16A)=Sof(O5A)=1-FVAR(1)
Sof(H16)=Sof(O5B)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
N2(H2), N1(H1), C4(H4), C3(H3), C11(H11), C1(H1A), C2(H2A), C12(H12),
C16(H16), C16(H16A)
3.b Idealised Me refined as rotating group:
C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens geom
_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 0.35865(6) 0.92496(6) 0.18845(4) 0.04924(17) Uani 1 1 d . . . . .
S2 S 0.69544(7) 1.00371(7) 0.35625(5) 0.0622(2) Uani 1 1 d . . . . .
O3 O 0.41329(17) 0.80319(17) 0.13895(13) 0.0581(4) Uani 1 1 d . . . . .
O1 O 0.11404(17) 0.61233(16) 0.47383(13) 0.0601(4) Uani 1 1 d . . . . .
O2 O 0.53585(17) 0.72437(17) 0.50832(13) 0.0583(4) Uani 1 1 d . . . . .
O4 O 0.27804(18) 1.04101(18) 0.11992(14) 0.0672(5) Uani 1 1 d . . . . .
N3 N 0.25239(18) 0.86108(18) 0.32157(14) 0.0456(4) Uani 1 1 d . . . . .
N2 N 0.30084(19) 0.55867(19) 0.58290(15) 0.0523(4) Uani 1 1 d . . . . .
H2 H 0.389447 0.581561 0.585481 0.063 Uiso 1 1 calc R . . . .
N1 N 0.1038(2) 0.39472(19) 0.66938(15) 0.0524(4) Uani 1 1 d . . . . .
H1 H 0.063598 0.434906 0.607865 0.063 Uiso 1 1 calc R . . . .
C5 C 0.2360(2) 0.4440(2) 0.67318(18) 0.0479(5) Uani 1 1 d . . . . .
C9 C 0.5423(2) 0.9260(2) 0.33681(18) 0.0481(5) Uani 1 1 d . . . . .
C7 C 0.3270(2) 0.7633(2) 0.41123(17) 0.0451(5) Uani 1 1 d . . . . .
C6 C 0.2389(2) 0.6424(2) 0.48718(18) 0.0478(5) Uani 1 1 d . . . . .
C8 C 0.4672(2) 0.7973(2) 0.42670(17) 0.0468(5) Uani 1 1 d . . . . .
C10 C 0.5073(2) 0.9950(2) 0.22682(18) 0.0484(5) Uani 1 1 d . . . . .
N4 N 0.7999(3) 0.5891(2) 0.8162(3) 0.0779(6) Uani 1 1 d . . . . .
C4 C 0.3025(3) 0.3762(2) 0.7712(2) 0.0570(6) Uani 1 1 d . . . . .
H4 H 0.395329 0.406757 0.775525 0.068 Uiso 1 1 calc R . . . .
C3 C 0.2303(3) 0.2643(3) 0.8610(2) 0.0636(6) Uani 1 1 d . . . . .
H3 H 0.274589 0.218331 0.926539 0.076 Uiso 1 1 calc R . . . .
C11 C 0.6035(3) 1.1119(3) 0.1577(2) 0.0603(6) Uani 1 1 d . . . . .
H11 H 0.595284 1.169419 0.080913 0.072 Uiso 1 1 calc R . . . .
C1 C 0.0306(3) 0.2845(2) 0.7579(2) 0.0603(6) Uani 1 1 d . . . . .
H1A H -0.061518 0.254025 0.751852 0.072 Uiso 1 1 calc R . . . .
C2 C 0.0918(3) 0.2187(3) 0.8553(2) 0.0661(7) Uani 1 1 d . . . . .
H2A H 0.041570 0.144090 0.917481 0.079 Uiso 1 1 calc R . . . .
C13 C 0.1400(3) 0.9623(3) 0.3699(2) 0.0651(6) Uani 1 1 d . . . . .
H13A H 0.189360 1.029916 0.396928 0.098 Uiso 1 1 calc GR . . . .
H13B H 0.068623 0.907079 0.437124 0.098 Uiso 1 1 calc GR . . . .
H13C H 0.088571 1.015897 0.307363 0.098 Uiso 1 1 calc GR . . . .
C12 C 0.7093(3) 1.1285(3) 0.2188(2) 0.0683(7) Uani 1 1 d . . . . .
H12 H 0.781847 1.200549 0.188695 0.082 Uiso 1 1 calc R . . . .
C15 C 0.7273(6) 0.6178(5) 0.7171(4) 0.1445(18) Uani 1 1 d . . . . .
H15A H 0.692175 0.527382 0.710813 0.217 Uiso 1 1 calc GR . . . .
H15B H 0.796887 0.661379 0.643646 0.217 Uiso 1 1 calc GR . . . .
H15C H 0.643472 0.684125 0.729233 0.217 Uiso 1 1 calc GR . . . .
C14 C 0.7195(6) 0.5060(5) 0.9315(4) 0.158(2) Uani 1 1 d . . . . .
H14A H 0.640362 0.566307 0.964158 0.237 Uiso 1 1 calc GR . . . .
H14B H 0.787242 0.474488 0.986448 0.237 Uiso 1 1 calc GR . . . .
H14C H 0.676943 0.421512 0.920871 0.237 Uiso 1 1 calc GR . . . .
C16 C 0.9315(5) 0.6388(5) 0.8105(8) 0.158(3) Uani 1 1 d . . . . .
H16 H 0.962864 0.703204 0.734550 0.190 Uiso 0.346(18) 1 calc R . P A 1
H16A H 0.945401 0.610516 0.890243 0.190 Uiso 0.654(18) 1 calc R . P A 2
O5B O 1.0177(9) 0.6309(9) 0.8642(13) 0.090(4) Uani 0.346(18) 1 d . . P A 1
O5A O 1.0235(6) 0.6914(10) 0.7639(14) 0.146(5) Uani 0.654(18) 1 d . . P A 2
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 0.0525(3) 0.0531(3) 0.0394(3) 0.0025(2) -0.0194(2) -0.0070(2)
S2 0.0587(4) 0.0775(4) 0.0573(4) -0.0191(3) -0.0204(3) -0.0122(3)
O3 0.0632(10) 0.0695(10) 0.0469(9) -0.0176(7) -0.0175(7) -0.0061(7)
O1 0.0590(10) 0.0614(10) 0.0531(9) 0.0114(7) -0.0257(7) -0.0122(7)
O2 0.0552(9) 0.0696(10) 0.0470(8) 0.0011(7) -0.0244(7) 0.0005(7)
O4 0.0684(10) 0.0653(10) 0.0567(10) 0.0182(8) -0.0295(8) -0.0066(8)
N3 0.0436(9) 0.0477(10) 0.0403(9) 0.0034(7) -0.0163(7) 0.0006(7)
N2 0.0495(10) 0.0562(11) 0.0439(10) 0.0065(8) -0.0184(8) -0.0004(8)
N1 0.0608(11) 0.0504(10) 0.0418(10) 0.0029(8) -0.0200(8) -0.0003(8)
C5 0.0514(12) 0.0461(11) 0.0417(11) -0.0016(9) -0.0138(9) 0.0043(9)
C9 0.0469(11) 0.0539(12) 0.0448(11) -0.0119(9) -0.0123(9) -0.0025(9)
C7 0.0474(11) 0.0470(11) 0.0372(10) -0.0004(8) -0.0152(8) 0.0027(8)
C6 0.0506(12) 0.0501(12) 0.0397(11) -0.0020(9) -0.0163(9) 0.0042(9)
C8 0.0511(12) 0.0514(12) 0.0367(10) -0.0068(9) -0.0138(9) 0.0046(9)
C10 0.0516(12) 0.0500(12) 0.0428(11) -0.0056(9) -0.0141(9) -0.0061(9)
N4 0.0625(13) 0.0702(14) 0.1090(19) -0.0320(13) -0.0211(13) -0.0070(11)
C4 0.0590(13) 0.0598(14) 0.0479(12) -0.0002(10) -0.0210(10) 0.0051(10)
C3 0.0790(17) 0.0607(14) 0.0450(12) 0.0046(10) -0.0249(11) 0.0065(12)
C11 0.0659(15) 0.0564(14) 0.0554(14) -0.0033(10) -0.0145(11) -0.0151(11)
C1 0.0696(15) 0.0522(13) 0.0521(13) 0.0034(10) -0.0158(11) -0.0089(11)
C2 0.0798(17) 0.0560(14) 0.0511(14) 0.0088(11) -0.0149(12) -0.0069(12)
C13 0.0633(14) 0.0614(14) 0.0631(15) -0.0043(11) -0.0167(11) 0.0132(11)
C12 0.0695(16) 0.0673(16) 0.0681(16) -0.0121(12) -0.0137(12) -0.0217(12)
C15 0.187(4) 0.142(4) 0.142(4) -0.071(3) -0.095(3) 0.065(3)
C14 0.213(5) 0.147(4) 0.111(3) -0.037(3) 0.000(3) -0.063(4)
C16 0.073(3) 0.089(3) 0.330(8) -0.107(4) -0.013(5) 0.000(3)
O5B 0.060(5) 0.090(5) 0.116(9) -0.004(5) -0.031(4) -0.024(3)
O5A 0.076(3) 0.127(6) 0.262(14) -0.099(8) -0.026(4) -0.012(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
S1 O3 1.4291(16) . ?
S1 O4 1.4279(15) . ?
S1 N3 1.6278(17) . ?
S1 C10 1.740(2) . ?
S2 C9 1.708(2) . ?
S2 C12 1.703(3) . ?
O1 C6 1.244(2) . ?
O2 C8 1.269(2) . ?
N3 C7 1.450(2) . ?
N3 C13 1.471(3) . ?
N2 H2 0.8600 . ?
N2 C5 1.360(3) . ?
N2 C6 1.386(2) . ?
N1 H1 0.8600 . ?
N1 C5 1.337(3) . ?
N1 C1 1.353(3) . ?
C5 C4 1.389(3) . ?
C9 C8 1.477(3) . ?
C9 C10 1.367(3) . ?
C7 C6 1.423(3) . ?
C7 C8 1.400(3) . ?
C10 C11 1.416(3) . ?
N4 C15 1.407(4) . ?
N4 C14 1.434(5) . ?
N4 C16 1.303(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.365(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.384(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.356(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.352(3) . ?
C2 H2A 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16 0.9300 . ?
C16 H16A 0.9300 . ?
C16 O5B 1.092(11) . ?
C16 O5A 0.983(10) . ?
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 N3 107.93(9) . . ?
O3 S1 C10 108.75(10) . . ?
O4 S1 O3 118.48(10) . . ?
O4 S1 N3 108.44(10) . . ?
O4 S1 C10 110.37(10) . . ?
N3 S1 C10 101.49(9) . . ?
C12 S2 C9 91.78(11) . . ?
C7 N3 S1 115.56(13) . . ?
C7 N3 C13 114.51(16) . . ?
C13 N3 S1 117.59(14) . . ?
C5 N2 H2 116.6 . . ?
C5 N2 C6 126.73(18) . . ?
C6 N2 H2 116.6 . . ?
C5 N1 H1 118.5 . . ?
C5 N1 C1 122.97(19) . . ?
C1 N1 H1 118.5 . . ?
N2 C5 C4 121.9(2) . . ?
N1 C5 N2 119.80(18) . . ?
N1 C5 C4 118.32(19) . . ?
C8 C9 S2 122.70(15) . . ?
C10 C9 S2 110.54(15) . . ?
C10 C9 C8 126.70(19) . . ?
C6 C7 N3 114.14(17) . . ?
C8 C7 N3 121.01(17) . . ?
C8 C7 C6 124.55(18) . . ?
O1 C6 N2 120.63(18) . . ?
O1 C6 C7 124.64(18) . . ?
N2 C6 C7 114.72(18) . . ?
O2 C8 C9 118.14(18) . . ?
O2 C8 C7 125.48(19) . . ?
C7 C8 C9 116.34(17) . . ?
C9 C10 S1 116.93(15) . . ?
C9 C10 C11 113.94(19) . . ?
C11 C10 S1 129.09(17) . . ?
C15 N4 C14 117.3(4) . . ?
C16 N4 C15 124.0(5) . . ?
C16 N4 C14 118.6(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C10 C11 H11 124.7 . . ?
C12 C11 C10 110.7(2) . . ?
C12 C11 H11 124.7 . . ?
N1 C1 H1A 120.1 . . ?
C2 C1 N1 119.7(2) . . ?
C2 C1 H1A 120.1 . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2A 120.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S2 C12 H12 123.5 . . ?
C11 C12 S2 113.05(18) . . ?
C11 C12 H12 123.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C16 H16 109.2 . . ?
N4 C16 H16A 104.5 . . ?
O5B C16 N4 141.7(11) . . ?
O5B C16 H16 109.2 . . ?
O5A C16 N4 151.0(13) . . ?
O5A C16 H16A 104.5 . . ?
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
_geom_hbond_publ_flag
N2 H2 O2 0.86 1.88 2.602(2) 141.2 . yes
N1 H1 O1 0.86 2.17 2.871(2) 137.9 2_566 yes
N1 H1 O1 0.86 1.97 2.620(2) 131.8 . yes
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 N3 C7 C6 -141.06(16) . . . . ?
S1 N3 C7 C8 45.1(2) . . . . ?
S1 C10 C11 C12 -177.67(19) . . . . ?
S2 C9 C8 O2 -14.5(3) . . . . ?
S2 C9 C8 C7 167.80(15) . . . . ?
S2 C9 C10 S1 177.26(11) . . . . ?
S2 C9 C10 C11 -0.4(3) . . . . ?
O3 S1 N3 C7 62.41(16) . . . . ?
O3 S1 N3 C13 -157.35(16) . . . . ?
O3 S1 C10 C9 -82.94(19) . . . . ?
O3 S1 C10 C11 94.3(2) . . . . ?
O4 S1 N3 C7 -168.08(14) . . . . ?
O4 S1 N3 C13 -27.83(19) . . . . ?
O4 S1 C10 C9 145.51(17) . . . . ?
O4 S1 C10 C11 -37.2(3) . . . . ?
N3 S1 C10 C9 30.68(19) . . . . ?
N3 S1 C10 C11 -152.1(2) . . . . ?
N3 C7 C6 O1 6.1(3) . . . . ?
N3 C7 C6 N2 -172.22(17) . . . . ?
N3 C7 C8 O2 174.60(19) . . . . ?
N3 C7 C8 C9 -7.9(3) . . . . ?
N2 C5 C4 C3 178.1(2) . . . . ?
N1 C5 C4 C3 -1.3(3) . . . . ?
N1 C1 C2 C3 -1.2(4) . . . . ?
C5 N2 C6 O1 -3.2(3) . . . . ?
C5 N2 C6 C7 175.2(2) . . . . ?
C5 N1 C1 C2 -0.4(4) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C9 S2 C12 C11 -1.0(2) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C6 N2 C5 N1 5.5(3) . . . . ?
C6 N2 C5 C4 -173.9(2) . . . . ?
C6 C7 C8 O2 1.4(3) . . . . ?
C6 C7 C8 C9 178.93(19) . . . . ?
C8 C9 C10 S1 0.3(3) . . . . ?
C8 C9 C10 C11 -177.4(2) . . . . ?
C8 C7 C6 O1 179.7(2) . . . . ?
C8 C7 C6 N2 1.4(3) . . . . ?
C10 S1 N3 C7 -51.83(16) . . . . ?
C10 S1 N3 C13 88.42(17) . . . . ?
C10 C9 C8 O2 162.2(2) . . . . ?
C10 C9 C8 C7 -15.6(3) . . . . ?
C10 C11 C12 S2 1.0(3) . . . . ?
C4 C3 C2 C1 1.5(4) . . . . ?
C1 N1 C5 N2 -177.8(2) . . . . ?
C1 N1 C5 C4 1.7(3) . . . . ?
C13 N3 C7 C6 77.5(2) . . . . ?
C13 N3 C7 C8 -96.4(2) . . . . ?
C12 S2 C9 C8 177.92(19) . . . . ?
C12 S2 C9 C10 0.79(18) . . . . ?
C15 N4 C16 O5B -173.7(9) . . . . ?
C15 N4 C16 O5A -5.6(12) . . . . ?
C14 N4 C16 O5B 9.6(11) . . . . ?
C14 N4 C16 O5A 177.7(10) . . . . ?
_shelx_res_file
;
TITL
txm_dmfa.res
created by SHELXL-2017/1 at 12:25:49 on 15-Jan-2019
CELL 0.71073 9.105952 9.438066 11.658566 74.5298 77.5002 85.5445
ZERR 2 0.00036 0.000392 0.000588 0.004 0.0038 0.0033
LATT 1
SFAC C H N O S
UNIT 32 36 8 10 4
EQIV $1 -X,1-Y,1-Z
L.S. 10 0 0
PLAN 20
SIZE 0.144 0.24 0.45
HTAB N2 O2
HTAB N1 O1
HTAB N1 O1_$1
BOND
BOND $H
CONF
fmap 2
acta
REM
REM
REM
WGHT 0.058600 0.145200
FVAR 0.47410 0.34586
S1 5 0.358650 0.924965 0.188451 11.00000 0.05250 0.05307 =
0.03937 0.00253 -0.01940 -0.00696
S2 5 0.695440 1.003708 0.356251 11.00000 0.05872 0.07755 =
0.05732 -0.01914 -0.02041 -0.01221
O3 4 0.413292 0.803185 0.138948 11.00000 0.06323 0.06954 =
0.04695 -0.01764 -0.01746 -0.00615
O1 4 0.114036 0.612327 0.473835 11.00000 0.05903 0.06139 =
0.05308 0.01139 -0.02570 -0.01220
O2 4 0.535855 0.724365 0.508319 11.00000 0.05522 0.06965 =
0.04703 0.00110 -0.02444 0.00053
O4 4 0.278043 1.041011 0.119920 11.00000 0.06836 0.06527 =
0.05674 0.01821 -0.02952 -0.00659
N3 3 0.252390 0.861085 0.321571 11.00000 0.04365 0.04769 =
0.04035 0.00339 -0.01634 0.00059
N2 3 0.300844 0.558670 0.582899 11.00000 0.04952 0.05622 =
0.04392 0.00645 -0.01835 -0.00043
AFIX 43
H2 2 0.389447 0.581561 0.585481 11.00000 -1.20000
AFIX 0
N1 3 0.103844 0.394717 0.669382 11.00000 0.06084 0.05037 =
0.04179 0.00294 -0.01998 -0.00029
AFIX 43
H1 2 0.063598 0.434906 0.607865 11.00000 -1.20000
AFIX 0
C5 1 0.235979 0.444009 0.673179 11.00000 0.05141 0.04606 =
0.04167 -0.00165 -0.01379 0.00427
C9 1 0.542302 0.926031 0.336811 11.00000 0.04686 0.05386 =
0.04482 -0.01191 -0.01229 -0.00249
C7 1 0.326985 0.763310 0.411234 11.00000 0.04737 0.04698 =
0.03716 -0.00039 -0.01516 0.00269
C6 1 0.238891 0.642422 0.487178 11.00000 0.05059 0.05005 =
0.03971 -0.00203 -0.01634 0.00423
C8 1 0.467219 0.797340 0.426702 11.00000 0.05110 0.05140 =
0.03666 -0.00680 -0.01381 0.00456
C10 1 0.507336 0.995001 0.226824 11.00000 0.05159 0.04995 =
0.04280 -0.00563 -0.01405 -0.00615
N4 3 0.799867 0.589067 0.816224 11.00000 0.06251 0.07021 =
0.10898 -0.03198 -0.02110 -0.00700
C4 1 0.302481 0.376202 0.771163 11.00000 0.05901 0.05984 =
0.04791 -0.00025 -0.02101 0.00511
AFIX 43
H4 2 0.395329 0.406757 0.775525 11.00000 -1.20000
AFIX 0
C3 1 0.230300 0.264338 0.860959 11.00000 0.07897 0.06072 =
0.04495 0.00465 -0.02485 0.00648
AFIX 43
H3 2 0.274589 0.218331 0.926539 11.00000 -1.20000
AFIX 0
C11 1 0.603504 1.111896 0.157684 11.00000 0.06586 0.05642 =
0.05542 -0.00329 -0.01445 -0.01508
AFIX 43
H11 2 0.595284 1.169419 0.080913 11.00000 -1.20000
AFIX 0
C1 1 0.030576 0.284479 0.757928 11.00000 0.06957 0.05221 =
0.05206 0.00340 -0.01579 -0.00895
AFIX 43
H1A 2 -0.061518 0.254025 0.751852 11.00000 -1.20000
AFIX 0
C2 1 0.091757 0.218741 0.855303 11.00000 0.07975 0.05599 =
0.05111 0.00878 -0.01486 -0.00695
AFIX 43
H2A 2 0.041570 0.144090 0.917481 11.00000 -1.20000
AFIX 0
C13 1 0.139974 0.962283 0.369947 11.00000 0.06325 0.06138 =
0.06306 -0.00430 -0.01667 0.01324
AFIX 137
H13A 2 0.189360 1.029916 0.396928 11.00000 -1.50000
H13B 2 0.068623 0.907079 0.437124 11.00000 -1.50000
H13C 2 0.088571 1.015897 0.307363 11.00000 -1.50000
AFIX 0
C12 1 0.709256 1.128475 0.218773 11.00000 0.06952 0.06733 =
0.06814 -0.01206 -0.01375 -0.02175
AFIX 43
H12 2 0.781847 1.200549 0.188695 11.00000 -1.20000
AFIX 0
C15 1 0.727336 0.617769 0.717102 11.00000 0.18699 0.14215 =
0.14211 -0.07096 -0.09509 0.06479
AFIX 137
H15A 2 0.692175 0.527382 0.710813 11.00000 -1.50000
H15B 2 0.796887 0.661379 0.643646 11.00000 -1.50000
H15C 2 0.643472 0.684125 0.729233 11.00000 -1.50000
AFIX 0
C14 1 0.719455 0.505974 0.931451 11.00000 0.21292 0.14713 =
0.11115 -0.03723 -0.00048 -0.06268
AFIX 137
H14A 2 0.640362 0.566307 0.964158 11.00000 -1.50000
H14B 2 0.787242 0.474488 0.986448 11.00000 -1.50000
H14C 2 0.676943 0.421512 0.920871 11.00000 -1.50000
AFIX 0
C16 1 0.931547 0.638836 0.810488 11.00000 0.07260 0.08918 =
0.32980 -0.10652 -0.01331 0.00005
PART 1
AFIX 43
H16 2 0.962864 0.703204 0.734550 21.00000 -1.20000
AFIX 43
PART 0
PART 2
H16A 2 0.945401 0.610516 0.890243 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
O5B 4 1.017692 0.630924 0.864190 21.00000 0.06042 0.08983 =
0.11635 -0.00352 -0.03113 -0.02419
PART 0
PART 2
O5A 4 1.023545 0.691406 0.763861 -21.00000 0.07612 0.12652 =
0.26154 -0.09899 -0.02645 -0.01232
HKLF 4
REM
REM R1 = 0.0427 for 2958 Fo > 4sig(Fo) and 0.0585 for all 3857 data
REM 257 parameters refined using 0 restraints
END
WGHT 0.0586 0.1452
REM Highest difference peak 0.253, deepest hole -0.305, 1-sigma level 0.042
Q1 1 0.4579 0.9538 0.2035 11.00000 0.05 0.25
Q2 1 0.9124 0.6880 0.6852 11.00000 0.05 0.24
Q3 1 0.4034 0.8760 0.1189 11.00000 0.05 0.19
Q4 1 0.5230 0.8751 0.3579 11.00000 0.05 0.18
Q5 1 0.5891 0.9595 0.3341 11.00000 0.05 0.17
Q6 1 0.4995 0.9818 0.2965 11.00000 0.05 0.17
Q7 1 0.3283 0.7088 0.4079 11.00000 0.05 0.17
Q8 1 0.3095 0.8997 0.2785 11.00000 0.05 0.17
Q9 1 0.5245 1.0516 0.1964 11.00000 0.05 0.15
Q10 1 0.2702 1.0453 0.1793 11.00000 0.05 0.15
Q11 1 0.2921 0.8126 0.3598 11.00000 0.05 0.15
Q12 1 0.4501 0.7747 0.1043 11.00000 0.05 0.15
Q13 1 0.8295 0.6553 0.7868 11.00000 0.05 0.14
Q14 1 0.8301 0.5939 0.8994 11.00000 0.05 0.14
Q15 1 -0.0304 0.1658 0.9771 11.00000 0.05 0.14
Q16 1 0.1524 0.2661 0.8692 11.00000 0.05 0.14
Q17 1 1.0050 0.5655 0.9086 11.00000 0.05 0.14
Q18 1 0.4420 0.7923 0.1740 11.00000 0.05 0.13
Q19 1 0.2574 0.3201 0.8226 11.00000 0.05 0.13
Q20 1 0.1955 1.1513 0.1609 11.00000 0.05 0.13
;
_shelx_res_checksum 18611
_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 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.814
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMFA'
#######################################################################
#
# 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_tnx_chcl3_III
_database_code_depnum_ccdc_archive 'CCDC 1904022'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record
;
2019-07-05 deposited with the CCDC. 2019-07-12 downloaded from the CCDC.
;
_audit_creation_date 2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common 'tenoxicam chloroform III solvate'
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H11 N3 O4 S2, C H Cl3'
_chemical_formula_sum 'C14 H12 Cl3 N3 O4 S2'
_chemical_formula_weight 456.74
_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 0.0047 0.0021 '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 0.1752 0.1990 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0086 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0149 0.0078 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1474 0.1548 '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 13.579(3)
_cell_length_b 10.135(2)
_cell_length_c 14.880(3)
_cell_angle_alpha 90
_cell_angle_beta 116.58(3)
_cell_angle_gamma 90
_cell_volume 1831.3(8)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 600
_cell_measurement_temperature 100(1)
_cell_measurement_theta_max 62.018
_cell_measurement_theta_min 3.746
_shelx_estimated_absorpt_T_max 0.922
_shelx_estimated_absorpt_T_min 0.903
_exptl_absorpt_coefficient_mu 1.037
_exptl_absorpt_correction_T_max 1
_exptl_absorpt_correction_T_min 0.911
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'XDS (Kabsch, 2010)'
_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 1.657
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 928
_exptl_crystal_size_max 0.1
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.08
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0374
_diffrn_reflns_av_unetI/netI 0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 17905
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full 28.439
_diffrn_reflns_theta_max 31.009
_diffrn_reflns_theta_min 1.873
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type 'Rayonix SX165 CCD'
_diffrn_measurement_method /f
_diffrn_radiation_type synchrotron
_diffrn_radiation_wavelength 0.7937
_diffrn_source ?
_diffrn_special_details ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3593
_reflns_number_total 4021
_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 0.340
_refine_diff_density_min -0.557
_refine_diff_density_rms 0.084
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.056
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 236
_refine_ls_number_reflns 4021
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0475
_refine_ls_R_factor_gt 0.0424
_refine_ls_restrained_S_all 1.056
_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^)+(0.0608P)^2^+1.8294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1080
_refine_ls_wR_factor_ref 0.1115
_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 Ternary CH refined with riding coordinates:
C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
N2(H2), N1(H1), C4(H4), C2(H2A), C1(H1A), C11(H11), C3(H3), C12(H12)
2.c Idealised Me refined as rotating group:
C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_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 0.25364(4) 0.16931(5) 0.68506(4) 0.02317(14) Uani 1 1 d . . . . .
S2 S 0.05269(5) 0.40120(6) 0.43571(4) 0.02657(14) Uani 1 1 d . . . . .
Cl2 Cl 0.20697(5) 0.65664(6) 0.35327(5) 0.03248(15) Uani 1 1 d . . . . .
Cl3 Cl 0.06387(5) 0.87197(6) 0.34536(5) 0.03238(15) Uani 1 1 d . . . . .
Cl1 Cl 0.28931(5) 0.86807(7) 0.50112(5) 0.04031(17) Uani 1 1 d . . . . .
O4 O 0.21063(14) 0.05859(15) 0.71635(13) 0.0287(4) Uani 1 1 d . . . . .
O2 O 0.23034(13) 0.57656(15) 0.59179(12) 0.0264(3) Uani 1 1 d . . . . .
O1 O 0.42286(13) 0.46319(15) 0.89212(12) 0.0260(3) Uani 1 1 d . . . . .
O3 O 0.35526(13) 0.15433(15) 0.67901(13) 0.0282(4) Uani 1 1 d . . . . .
N2 N 0.37384(16) 0.62970(17) 0.77445(15) 0.0236(4) Uani 1 1 d . . . . .
H2 H 0.332387 0.649745 0.710976 0.028 Uiso 1 1 calc R . . . .
N1 N 0.50341(15) 0.70430(18) 0.93226(14) 0.0229(4) Uani 1 1 d . . . . .
H1 H 0.500098 0.626216 0.956629 0.028 Uiso 1 1 calc R . . . .
N3 N 0.26620(15) 0.29413(18) 0.75938(14) 0.0228(4) Uani 1 1 d . . . . .
C6 C 0.36552(17) 0.5013(2) 0.80418(17) 0.0220(4) Uani 1 1 d . . . . .
C5 C 0.44001(17) 0.7271(2) 0.83428(17) 0.0220(4) Uani 1 1 d . . . . .
C8 C 0.22502(17) 0.4626(2) 0.62551(17) 0.0225(4) Uani 1 1 d . . . . .
C7 C 0.28650(17) 0.4206(2) 0.72562(17) 0.0222(4) Uani 1 1 d . . . . .
C4 C 0.44225(18) 0.8529(2) 0.79579(18) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.395944 0.872900 0.727256 0.029 Uiso 1 1 calc R . . . .
C9 C 0.15211(18) 0.3628(2) 0.55414(18) 0.0241(4) Uani 1 1 d . . . . .
C10 C 0.15369(18) 0.2291(2) 0.57016(17) 0.0241(4) Uani 1 1 d . . . . .
C13 C 0.18592(19) 0.3017(2) 0.80151(19) 0.0285(5) Uani 1 1 d . . . . .
H13A H 0.114805 0.332467 0.749468 0.043 Uiso 1 1 calc GR . . . .
H13B H 0.212946 0.363453 0.858151 0.043 Uiso 1 1 calc GR . . . .
H13C H 0.176961 0.214057 0.824742 0.043 Uiso 1 1 calc GR . . . .
C2 C 0.57950(19) 0.9183(2) 0.95995(18) 0.0273(5) Uani 1 1 d . . . . .
H2A H 0.628984 0.982577 1.003110 0.033 Uiso 1 1 calc R . . . .
C1 C 0.57253(18) 0.7961(2) 0.99570(18) 0.0260(5) Uani 1 1 d . . . . .
H1A H 0.615889 0.775533 1.064662 0.031 Uiso 1 1 calc R . . . .
C11 C 0.0738(2) 0.1575(2) 0.48872(18) 0.0280(5) Uani 1 1 d . . . . .
H11 H 0.064067 0.064611 0.488239 0.034 Uiso 1 1 calc R . . . .
C3 C 0.51242(19) 0.9468(2) 0.85866(18) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.515366 1.031773 0.833065 0.032 Uiso 1 1 calc R . . . .
C12 C 0.01252(19) 0.2391(2) 0.41107(18) 0.0298(5) Uani 1 1 d . . . . .
H12 H -0.046072 0.209723 0.349886 0.036 Uiso 1 1 calc R . . . .
C14 C 0.17425(19) 0.7703(2) 0.42575(18) 0.0273(5) Uani 1 1 d . . . . .
H14 H 0.150577 0.720093 0.470602 0.033 Uiso 1 1 calc 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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0252(3) 0.0171(2) 0.0268(3) 0.00044(18) 0.0113(2) -0.00144(18)
S2 0.0263(3) 0.0262(3) 0.0228(3) -0.0019(2) 0.0070(2) 0.0016(2)
Cl2 0.0375(3) 0.0294(3) 0.0300(3) 0.0028(2) 0.0146(2) 0.0098(2)
Cl3 0.0342(3) 0.0259(3) 0.0312(3) -0.0023(2) 0.0094(2) 0.0062(2)
Cl1 0.0354(3) 0.0450(4) 0.0329(4) -0.0036(3) 0.0085(3) -0.0123(3)
O4 0.0341(8) 0.0200(7) 0.0328(9) 0.0015(6) 0.0156(7) -0.0051(6)
O2 0.0313(8) 0.0186(7) 0.0256(8) 0.0023(6) 0.0094(6) -0.0001(6)
O1 0.0298(8) 0.0206(7) 0.0222(8) 0.0007(6) 0.0070(6) -0.0029(6)
O3 0.0276(8) 0.0225(7) 0.0356(10) 0.0017(6) 0.0152(7) 0.0020(6)
N2 0.0270(9) 0.0188(8) 0.0212(9) 0.0000(7) 0.0075(7) -0.0018(7)
N1 0.0249(9) 0.0189(8) 0.0224(9) 0.0002(7) 0.0082(7) -0.0017(7)
N3 0.0261(9) 0.0191(8) 0.0232(9) 0.0000(7) 0.0111(7) -0.0024(7)
C6 0.0243(10) 0.0186(9) 0.0232(11) 0.0000(8) 0.0108(8) 0.0004(7)
C5 0.0221(10) 0.0201(10) 0.0236(11) -0.0011(8) 0.0099(8) -0.0005(7)
C8 0.0242(10) 0.0186(9) 0.0234(11) -0.0001(8) 0.0094(8) 0.0007(8)
C7 0.0242(10) 0.0177(9) 0.0237(11) 0.0009(8) 0.0099(8) -0.0011(7)
C4 0.0249(10) 0.0211(10) 0.0260(12) 0.0022(8) 0.0104(9) 0.0009(8)
C9 0.0242(10) 0.0223(10) 0.0248(11) -0.0018(8) 0.0100(8) 0.0004(8)
C10 0.0243(10) 0.0211(10) 0.0273(12) -0.0034(8) 0.0119(9) -0.0025(8)
C13 0.0293(11) 0.0272(11) 0.0320(13) -0.0006(9) 0.0163(9) -0.0025(9)
C2 0.0273(11) 0.0212(10) 0.0309(12) -0.0039(8) 0.0106(9) -0.0050(8)
C1 0.0265(10) 0.0231(10) 0.0247(12) -0.0014(8) 0.0082(9) -0.0016(8)
C11 0.0314(12) 0.0273(11) 0.0281(12) -0.0068(9) 0.0158(10) -0.0083(9)
C3 0.0293(11) 0.0197(10) 0.0303(12) 0.0004(8) 0.0137(9) -0.0008(8)
C12 0.0281(11) 0.0333(12) 0.0272(12) -0.0080(9) 0.0115(9) -0.0059(9)
C14 0.0295(11) 0.0252(11) 0.0261(12) 0.0000(8) 0.0116(9) -0.0010(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 O4 1.4354(16) . ?
S1 O3 1.4305(17) . ?
S1 N3 1.6382(19) . ?
S1 C10 1.748(2) . ?
S2 C9 1.718(2) . ?
S2 C12 1.718(3) . ?
Cl2 C14 1.766(2) . ?
Cl3 C14 1.770(2) . ?
Cl1 C14 1.764(2) . ?
O2 C8 1.274(3) . ?
O1 C6 1.247(3) . ?
N2 H2 0.8800 . ?
N2 C6 1.395(3) . ?
N2 C5 1.363(3) . ?
N1 H1 0.8800 . ?
N1 C5 1.340(3) . ?
N1 C1 1.358(3) . ?
N3 C7 1.448(3) . ?
N3 C13 1.483(3) . ?
C6 C7 1.437(3) . ?
C5 C4 1.404(3) . ?
C8 C7 1.409(3) . ?
C8 C9 1.480(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.375(3) . ?
C9 C10 1.374(3) . ?
C10 C11 1.413(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C2 H2A 0.9500 . ?
C2 C1 1.367(3) . ?
C2 C3 1.399(3) . ?
C1 H1A 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.361(4) . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14 1.0000 . ?
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
O4 S1 N3 108.62(10) . . ?
O4 S1 C10 109.74(10) . . ?
O3 S1 O4 118.78(10) . . ?
O3 S1 N3 108.21(10) . . ?
O3 S1 C10 108.90(11) . . ?
N3 S1 C10 101.14(10) . . ?
C9 S2 C12 91.78(11) . . ?
C6 N2 H2 116.9 . . ?
C5 N2 H2 116.9 . . ?
C5 N2 C6 126.3(2) . . ?
C5 N1 H1 118.5 . . ?
C5 N1 C1 123.07(19) . . ?
C1 N1 H1 118.5 . . ?
C7 N3 S1 115.35(15) . . ?
C7 N3 C13 113.03(17) . . ?
C13 N3 S1 116.81(15) . . ?
O1 C6 N2 121.37(19) . . ?
O1 C6 C7 124.43(19) . . ?
N2 C6 C7 114.20(19) . . ?
N2 C5 C4 121.3(2) . . ?
N1 C5 N2 120.04(19) . . ?
N1 C5 C4 118.7(2) . . ?
O2 C8 C7 125.4(2) . . ?
O2 C8 C9 118.3(2) . . ?
C7 C8 C9 116.24(19) . . ?
C6 C7 N3 114.24(19) . . ?
C8 C7 N3 121.31(19) . . ?
C8 C7 C6 124.20(19) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C8 C9 S2 123.20(17) . . ?
C10 C9 S2 110.21(17) . . ?
C10 C9 C8 126.6(2) . . ?
C9 C10 S1 117.17(17) . . ?
C9 C10 C11 114.3(2) . . ?
C11 C10 S1 128.53(18) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C2 H2A 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C3 C2 H2A 120.6 . . ?
N1 C1 C2 119.8(2) . . ?
N1 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C10 C11 H11 124.5 . . ?
C12 C11 C10 111.0(2) . . ?
C12 C11 H11 124.5 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
S2 C12 H12 123.7 . . ?
C11 C12 S2 112.66(18) . . ?
C11 C12 H12 123.7 . . ?
Cl2 C14 Cl3 109.60(13) . . ?
Cl2 C14 H14 108.6 . . ?
Cl3 C14 H14 108.6 . . ?
Cl1 C14 Cl2 111.19(13) . . ?
Cl1 C14 Cl3 110.12(13) . . ?
Cl1 C14 H14 108.6 . . ?
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
_geom_hbond_publ_flag
N2 H2 O2 0.88 1.85 2.595(3) 141.4 . yes
N1 H1 O1 0.88 2.21 2.893(2) 134.5 3_667 yes
N1 H1 O1 0.88 1.96 2.634(2) 132.1 . yes
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 N3 C7 C6 -139.58(17) . . . . ?
S1 N3 C7 C8 46.0(3) . . . . ?
S1 C10 C11 C12 -178.30(18) . . . . ?
S2 C9 C10 S1 177.41(12) . . . . ?
S2 C9 C10 C11 -1.4(3) . . . . ?
O4 S1 N3 C7 -167.59(15) . . . . ?
O4 S1 N3 C13 -31.18(19) . . . . ?
O4 S1 C10 C9 146.19(18) . . . . ?
O4 S1 C10 C11 -35.2(2) . . . . ?
O2 C8 C7 N3 173.2(2) . . . . ?
O2 C8 C7 C6 -0.7(4) . . . . ?
O2 C8 C9 S2 -14.7(3) . . . . ?
O2 C8 C9 C10 164.2(2) . . . . ?
O1 C6 C7 N3 8.3(3) . . . . ?
O1 C6 C7 C8 -177.4(2) . . . . ?
O3 S1 N3 C7 62.20(18) . . . . ?
O3 S1 N3 C13 -161.38(16) . . . . ?
O3 S1 C10 C9 -82.2(2) . . . . ?
O3 S1 C10 C11 96.4(2) . . . . ?
N2 C6 C7 N3 -171.57(18) . . . . ?
N2 C6 C7 C8 2.7(3) . . . . ?
N2 C5 C4 C3 -178.4(2) . . . . ?
N1 C5 C4 C3 2.6(3) . . . . ?
N3 S1 C10 C9 31.6(2) . . . . ?
N3 S1 C10 C11 -149.8(2) . . . . ?
C6 N2 C5 N1 -1.5(3) . . . . ?
C6 N2 C5 C4 179.5(2) . . . . ?
C5 N2 C6 O1 -1.6(3) . . . . ?
C5 N2 C6 C7 178.3(2) . . . . ?
C5 N1 C1 C2 -0.1(3) . . . . ?
C5 C4 C3 C2 -1.0(3) . . . . ?
C8 C9 C10 S1 -1.6(3) . . . . ?
C8 C9 C10 C11 179.6(2) . . . . ?
C7 C8 C9 S2 167.65(17) . . . . ?
C7 C8 C9 C10 -13.5(3) . . . . ?
C9 S2 C12 C11 -1.4(2) . . . . ?
C9 C8 C7 N3 -9.4(3) . . . . ?
C9 C8 C7 C6 176.7(2) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 S1 N3 C7 -52.15(17) . . . . ?
C10 S1 N3 C13 84.27(17) . . . . ?
C10 C11 C12 S2 0.9(3) . . . . ?
C13 N3 C7 C6 82.4(2) . . . . ?
C13 N3 C7 C8 -92.1(2) . . . . ?
C1 N1 C5 N2 178.9(2) . . . . ?
C1 N1 C5 C4 -2.1(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C3 C2 C1 N1 1.7(3) . . . . ?
C12 S2 C9 C8 -179.4(2) . . . . ?
C12 S2 C9 C10 1.58(19) . . . . ?
_shelx_res_file
;
TITL
tnxchcl3_iii.res
created by SHELXL-2017/1 at 11:02:37 on 01-Jul-2019
CELL 0.7937 13.579 10.135 14.88 90 116.583 90
ZERR 4 0.0027 0.002 0.003 0 0.03 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O S
DISP C 0.0047 0.0021 14.6915
DISP Cl 0.1752 0.199 936.4135
DISP H -0 0 0.6284
DISP N 0.0086 0.0042 25.9339
DISP O 0.0149 0.0078 43.7912
DISP S 0.1474 0.1548 735.5948
UNIT 56 48 12 12 16 8
EQIV $1 1-X,1-Y,2-Z
L.S. 4 0 0
PLAN 20
SIZE 0.08 0.1 0.1
TEMP -173.1(10)
HTAB N2 O2
HTAB N1 O1
HTAB N1 O1_$1
BOND
BOND $H
CONF
fmap 2 53
acta
REM
REM
REM
WGHT 0.060800 1.829400
FVAR 0.68287
S1 6 0.253639 0.169308 0.685056 11.00000 0.02522 0.01712 =
0.02682 0.00044 0.01134 -0.00144
S2 6 0.052690 0.401203 0.435713 11.00000 0.02627 0.02621 =
0.02277 -0.00187 0.00699 0.00159
CL2 3 0.206973 0.656644 0.353268 11.00000 0.03747 0.02941 =
0.02999 0.00276 0.01459 0.00983
CL3 3 0.063874 0.871967 0.345363 11.00000 0.03422 0.02593 =
0.03117 -0.00228 0.00943 0.00620
CL1 3 0.289306 0.868069 0.501118 11.00000 0.03544 0.04495 =
0.03287 -0.00359 0.00845 -0.01234
O4 5 0.210631 0.058593 0.716351 11.00000 0.03411 0.01997 =
0.03279 0.00149 0.01557 -0.00507
O2 5 0.230335 0.576562 0.591791 11.00000 0.03134 0.01865 =
0.02561 0.00230 0.00942 -0.00006
O1 5 0.422856 0.463194 0.892122 11.00000 0.02985 0.02063 =
0.02221 0.00070 0.00701 -0.00291
O3 5 0.355260 0.154327 0.679010 11.00000 0.02756 0.02252 =
0.03561 0.00174 0.01516 0.00205
N2 4 0.373838 0.629701 0.774453 11.00000 0.02702 0.01885 =
0.02124 -0.00004 0.00747 -0.00179
AFIX 43
H2 2 0.332387 0.649745 0.710976 11.00000 -1.20000
AFIX 0
N1 4 0.503411 0.704302 0.932262 11.00000 0.02489 0.01888 =
0.02240 0.00022 0.00819 -0.00173
AFIX 43
H1 2 0.500098 0.626216 0.956629 11.00000 -1.20000
AFIX 0
N3 4 0.266202 0.294131 0.759383 11.00000 0.02607 0.01913 =
0.02322 -0.00002 0.01106 -0.00237
C6 1 0.365515 0.501337 0.804179 11.00000 0.02431 0.01859 =
0.02324 0.00002 0.01078 0.00036
C5 1 0.440009 0.727073 0.834283 11.00000 0.02214 0.02006 =
0.02356 -0.00108 0.00990 -0.00047
C8 1 0.225017 0.462604 0.625508 11.00000 0.02418 0.01857 =
0.02340 -0.00008 0.00937 0.00072
C7 1 0.286499 0.420641 0.725620 11.00000 0.02420 0.01774 =
0.02366 0.00095 0.00986 -0.00109
C4 1 0.442255 0.852897 0.795786 11.00000 0.02492 0.02106 =
0.02601 0.00222 0.01045 0.00091
AFIX 43
H4 2 0.395944 0.872900 0.727256 11.00000 -1.20000
AFIX 0
C9 1 0.152107 0.362801 0.554138 11.00000 0.02417 0.02235 =
0.02480 -0.00180 0.01001 0.00044
C10 1 0.153691 0.229112 0.570164 11.00000 0.02429 0.02107 =
0.02730 -0.00337 0.01191 -0.00246
C13 1 0.185924 0.301665 0.801507 11.00000 0.02929 0.02725 =
0.03198 -0.00058 0.01634 -0.00248
AFIX 137
H13A 2 0.114805 0.332467 0.749468 11.00000 -1.50000
H13B 2 0.212946 0.363453 0.858151 11.00000 -1.50000
H13C 2 0.176961 0.214057 0.824742 11.00000 -1.50000
AFIX 0
C2 1 0.579503 0.918269 0.959951 11.00000 0.02729 0.02118 =
0.03086 -0.00387 0.01061 -0.00497
AFIX 43
H2A 2 0.628984 0.982577 1.003110 11.00000 -1.20000
AFIX 0
C1 1 0.572534 0.796116 0.995697 11.00000 0.02646 0.02308 =
0.02475 -0.00140 0.00822 -0.00164
AFIX 43
H1A 2 0.615889 0.775533 1.064662 11.00000 -1.20000
AFIX 0
C11 1 0.073765 0.157482 0.488721 11.00000 0.03143 0.02731 =
0.02809 -0.00676 0.01581 -0.00832
AFIX 43
H11 2 0.064067 0.064611 0.488239 11.00000 -1.20000
AFIX 0
C3 1 0.512422 0.946769 0.858661 11.00000 0.02931 0.01974 =
0.03028 0.00044 0.01366 -0.00083
AFIX 43
H3 2 0.515366 1.031773 0.833065 11.00000 -1.20000
AFIX 0
C12 1 0.012523 0.239140 0.411070 11.00000 0.02811 0.03329 =
0.02720 -0.00798 0.01155 -0.00594
AFIX 43
H12 2 -0.046072 0.209723 0.349886 11.00000 -1.20000
AFIX 0
C14 1 0.174252 0.770328 0.425750 11.00000 0.02955 0.02522 =
0.02613 0.00000 0.01159 -0.00099
AFIX 13
H14 2 0.150577 0.720093 0.470602 11.00000 -1.20000
AFIX 0
HKLF 4
REM
REM R1 = 0.0424 for 3593 Fo > 4sig(Fo) and 0.0475 for all 4021 data
REM 236 parameters refined using 0 restraints
END
WGHT 0.0608 1.8292
REM Highest difference peak 0.340, deepest hole -0.557, 1-sigma level 0.084
Q1 1 0.3848 0.8536 0.4941 11.00000 0.05 0.34
Q2 1 0.2017 0.6675 0.2585 11.00000 0.05 0.33
Q3 1 0.0335 0.8632 0.2437 11.00000 0.05 0.33
Q4 1 0.1391 0.6430 0.2613 11.00000 0.05 0.30
Q5 1 0.5362 0.9257 0.9013 11.00000 0.05 0.30
Q6 1 0.4758 0.8978 0.8389 11.00000 0.05 0.28
Q7 1 -0.0107 0.8292 0.3761 11.00000 0.05 0.27
Q8 1 0.1399 0.2974 0.5741 11.00000 0.05 0.27
Q9 1 0.3345 0.8418 0.5995 11.00000 0.05 0.27
Q10 1 0.1188 0.5961 0.3412 11.00000 0.05 0.26
Q11 1 0.3598 0.1467 0.7601 11.00000 0.05 0.26
Q12 1 0.3085 0.6406 0.4335 11.00000 0.05 0.26
Q13 1 0.2545 0.4418 0.6803 11.00000 0.05 0.25
Q14 1 0.1411 0.2111 0.6617 11.00000 0.05 0.25
Q15 1 0.1765 0.8934 0.4277 11.00000 0.05 0.25
Q16 1 0.1659 0.1438 0.6903 11.00000 0.05 0.24
Q17 1 0.0073 0.4061 0.3215 11.00000 0.05 0.24
Q18 1 -0.0150 0.9223 0.2426 11.00000 0.05 0.24
Q19 1 0.0984 0.1182 0.6612 11.00000 0.05 0.24
Q20 1 0.3644 0.9532 0.4793 11.00000 0.05 0.24
;
_shelx_res_checksum 11949
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform under -18 Celsius degree'
_chemical_properties_physical Heat-sensitive
#######################################################################
#
# 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_tnx_chcl3_I
_database_code_depnum_ccdc_archive 'CCDC 1890995'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record
;
2019-07-05 deposited with the CCDC. 2019-07-12 downloaded from the CCDC.
;
_audit_creation_date 2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common 'tenoxicam chloroform I solvate'
_chemical_name_systematic ?
_chemical_formula_moiety '2(C13 H11 N3 O4 S2), 2(C H Cl3)'
_chemical_formula_sum 'C28 H24 Cl6 N6 O8 S4'
_chemical_formula_weight 913.47
_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'
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 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 10.6019(12)
_cell_length_b 12.7810(10)
_cell_length_c 28.841(2)
_cell_angle_alpha 90
_cell_angle_beta 92.076(10)
_cell_angle_gamma 90
_cell_volume 3905.5(6)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2585
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 21.3050
_cell_measurement_theta_min 3.4580
_shelx_estimated_absorpt_T_max 0.914
_shelx_estimated_absorpt_T_min 0.816
_exptl_absorpt_coefficient_mu 0.708
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.64335
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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 1.554
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1856
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform under room temperature'
_exptl_crystal_size_max 0.3
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.13
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.2467
_diffrn_reflns_av_unetI/netI 0.1322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_number 54415
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.027
_diffrn_reflns_theta_max 25.027
_diffrn_reflns_theta_min 3.231
_diffrn_ambient_temperature 293(3)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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 -70.00 2.00 1.00 60.00 -- -11.27 127.00 94.42 72
2 \w -20.00 54.00 1.00 60.00 -- 11.43 77.00 150.00 74
3 \w -18.00 58.00 1.00 60.00 -- 11.43 57.00 -90.00 76
4 \w -58.00 41.00 1.00 60.00 -- 11.43 -57.00-120.00 99
5 \w -61.00 41.00 1.00 60.00 -- 11.43 -57.00 90.00 102
6 \w -65.00 45.00 1.00 60.00 -- 11.43 -77.00 0.00 110
7 \w -14.00 90.00 1.00 60.00 -- 11.43 77.00 0.00 104
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2586
_reflns_number_total 6880
_reflns_special_details
;
One chlorform molecule has a common C-H moiety (C14A H14A,H14B) with three
disordered chlorine sites (Cl1 and Cl1A, Cl2 and Cl2A, Cl3 and Cl3A) with 0.64(4) and 0.36(4)
atom occupancy ratio. Second chloroform molecule is completely disordered
(atom occupancy ratio is 0.545(13) and 0.455(13)). It was refine isotropically
with constraining the C-Cl distances equal d=1.78(2) angstrom.
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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.43 (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 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.757
_refine_diff_density_min -0.590
_refine_diff_density_rms 0.094
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 496
_refine_ls_number_reflns 6880
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.2576
_refine_ls_R_factor_gt 0.1163
_refine_ls_restrained_S_all 1.035
_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^)+(0.1678P)^2^+8.2269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.3158
_refine_ls_wR_factor_ref 0.3957
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Restrained distances
Cl4-C141 = Cl6-C141 = Cl5-C141 = Cl5A-C142 = Cl4A-C142 = Cl6A-C142
1.78 with sigma of 0.02
3. Others
Sof(H14B)=Sof(Cl2A)=Sof(Cl3A)=Sof(Cl1A)=1-FVAR(1)
Sof(Cl2)=Sof(Cl3)=Sof(Cl1)=Sof(H14A)=FVAR(1)
Sof(Cl4A)=Sof(Cl5A)=Sof(Cl6A)=Sof(C142)=Sof(H142)=1-FVAR(2)
Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=Sof(C141)=Sof(H141)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
C14A(H14A), C14A(H14B), C141(H141), C142(H142)
4.b Aromatic/amide H refined with riding coordinates:
N1A(H1A), N1B(H1B), N2A(H2A), N2B(H2B), C2A(H2AA), C3A(H3A), C11A(H11A),
C12A(H12A), C4A(H4A), C4B(H4B), C2B(H2BA), C11B(H11B), C1A(H1AA), C3B(H3B),
C12B(H12B), C1B(H1BA)
4.c Idealised Me refined as rotating group:
C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_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
S2A S 0.0736(3) 0.7459(2) 0.38459(9) 0.0708(9) Uani 1 1 d . . . . .
S1A S 0.1433(3) 0.8446(2) 0.52189(9) 0.0741(10) Uani 1 1 d . . . . .
S1B S 0.1598(4) 0.1690(2) 0.73255(10) 0.0871(11) Uani 1 1 d . . . . .
S2B S 0.1023(4) 0.2607(3) 0.86890(10) 0.0982(12) Uani 1 1 d . . . . .
O1A O 0.2518(7) 0.5625(5) 0.5831(2) 0.074(2) Uani 1 1 d . . . . .
Cl2 Cl 0.5942(19) 1.1427(14) 0.6331(7) 0.169(7) Uani 0.63(4) 1 d . . P A 1
O2A O 0.1084(7) 0.5565(5) 0.4456(2) 0.075(2) Uani 1 1 d . . . . .
O1B O 0.2737(8) 0.4500(5) 0.6757(2) 0.081(2) Uani 1 1 d . . . . .
Cl3 Cl 0.5936(13) 0.9958(12) 0.5600(4) 0.145(6) Uani 0.63(4) 1 d . . P A 1
N1A N 0.2402(8) 0.3550(6) 0.5846(3) 0.065(2) Uani 1 1 d . . . . .
H1A H 0.244481 0.409910 0.601789 0.078 Uiso 1 1 calc R . . . .
O4A O 0.2122(9) 0.9381(5) 0.5342(3) 0.097(3) Uani 1 1 d . . . . .
Cl1 Cl 0.517(2) 0.9280(19) 0.6458(7) 0.209(9) Uani 0.63(4) 1 d . . P A 1
O2B O 0.1480(9) 0.4512(6) 0.8117(2) 0.098(3) Uani 1 1 d . . . . .
N1B N 0.2410(9) 0.6551(6) 0.6736(3) 0.076(3) Uani 1 1 d . . . . .
H1B H 0.251594 0.599929 0.657121 0.092 Uiso 1 1 calc R . . . .
N2A N 0.1902(9) 0.4620(6) 0.5210(3) 0.073(3) Uani 1 1 d . . . . .
H2A H 0.159345 0.463808 0.493043 0.087 Uiso 1 1 calc R . . . .
N3A N 0.2350(10) 0.7445(6) 0.5314(3) 0.070(3) Uani 1 1 d . . . . .
O3B O 0.0450(10) 0.1965(7) 0.7085(3) 0.109(3) Uani 1 1 d . . . . .
C10A C 0.1172(10) 0.8386(7) 0.4628(3) 0.059(3) Uani 1 1 d . . . . .
C6A C 0.2135(10) 0.5589(7) 0.5419(3) 0.063(3) Uani 1 1 d . . . . .
O3A O 0.0287(9) 0.8252(6) 0.5439(3) 0.093(3) Uani 1 1 d . . . . .
C9A C 0.1159(10) 0.7420(8) 0.4429(3) 0.061(3) Uani 1 1 d . . . . .
N2B N 0.2188(10) 0.5493(7) 0.7379(3) 0.085(3) Uani 1 1 d . . . . .
H2B H 0.198879 0.546359 0.766471 0.102 Uiso 1 1 calc R . . . .
N3B N 0.2596(10) 0.2644(6) 0.7265(3) 0.073(3) Uani 1 1 d . . . . .
C8A C 0.1414(10) 0.6411(7) 0.4666(3) 0.058(3) Uani 1 1 d . . . . .
O4B O 0.2203(10) 0.0736(6) 0.7205(3) 0.116(3) Uani 1 1 d . . . . .
C10B C 0.1342(11) 0.1713(8) 0.7909(4) 0.073(3) Uani 1 1 d . . . . .
C2A C 0.2574(12) 0.1719(8) 0.5796(4) 0.082(4) Uani 1 1 d . . . . .
H2AA H 0.272279 0.106764 0.593107 0.099 Uiso 1 1 calc R . . . .
C5A C 0.2096(10) 0.3672(7) 0.5389(3) 0.057(3) Uani 1 1 d . . . . .
C3A C 0.2267(13) 0.1816(8) 0.5330(5) 0.091(4) Uani 1 1 d . . . . .
H3A H 0.222701 0.121758 0.514626 0.109 Uiso 1 1 calc R . . . .
C8B C 0.1722(11) 0.3677(8) 0.7901(3) 0.069(3) Uani 1 1 d . . . . .
C7A C 0.1907(11) 0.6465(7) 0.5121(3) 0.065(3) Uani 1 1 d . . . . .
C9B C 0.1416(11) 0.2683(9) 0.8127(3) 0.075(3) Uani 1 1 d . . . . .
C11A C 0.0857(10) 0.9180(8) 0.4307(4) 0.072(3) Uani 1 1 d . . . . .
H11A H 0.081844 0.988559 0.438387 0.086 Uiso 1 1 calc R . . . .
C5B C 0.2232(11) 0.6448(8) 0.7193(4) 0.073(3) Uani 1 1 d . . . . .
C12A C 0.0612(11) 0.8804(8) 0.3867(4) 0.076(3) Uani 1 1 d . . . . .
H12A H 0.040519 0.922314 0.361213 0.092 Uiso 1 1 calc R . . . .
C4A C 0.2018(12) 0.2776(9) 0.5127(4) 0.088(4) Uani 1 1 d . . . . .
H4A H 0.179709 0.281572 0.481234 0.106 Uiso 1 1 calc R . . . .
C6B C 0.2432(10) 0.4515(7) 0.7161(4) 0.064(3) Uani 1 1 d . . . . .
C7B C 0.2197(12) 0.3646(7) 0.7454(3) 0.076(3) Uani 1 1 d . . . . .
C4B C 0.2117(12) 0.7335(9) 0.7456(4) 0.090(4) Uani 1 1 d . . . . .
H4B H 0.201950 0.728554 0.777416 0.108 Uiso 1 1 calc R . . . .
C2B C 0.2294(12) 0.8376(8) 0.6778(4) 0.085(4) Uani 1 1 d . . . . .
H2BA H 0.230223 0.902811 0.663509 0.102 Uiso 1 1 calc R . . . .
C11B C 0.0937(11) 0.0924(11) 0.8207(4) 0.090(4) Uani 1 1 d . . . . .
H11B H 0.081742 0.023127 0.811749 0.109 Uiso 1 1 calc R . . . .
C1A C 0.2650(11) 0.2596(9) 0.6048(4) 0.079(3) Uani 1 1 d . . . . .
H1AA H 0.287140 0.255939 0.636255 0.095 Uiso 1 1 calc R . . . .
C13A C 0.3733(13) 0.7598(9) 0.5249(4) 0.092(4) Uani 1 1 d . . . . .
H13A H 0.390691 0.753736 0.492618 0.138 Uiso 1 1 calc GR . . . .
H13B H 0.419942 0.707357 0.542167 0.138 Uiso 1 1 calc GR . . . .
H13C H 0.398008 0.827912 0.535921 0.138 Uiso 1 1 calc GR . . . .
C3B C 0.2146(14) 0.8291(10) 0.7245(5) 0.099(4) Uani 1 1 d . . . . .
H3B H 0.206447 0.889411 0.742157 0.119 Uiso 1 1 calc R . . . .
C12B C 0.0744(12) 0.1279(11) 0.8629(5) 0.098(4) Uani 1 1 d . . . . .
H12B H 0.048489 0.085576 0.887016 0.118 Uiso 1 1 calc R . . . .
C1B C 0.2427(12) 0.7491(9) 0.6529(4) 0.083(4) Uani 1 1 d . . . . .
H1BA H 0.253215 0.753395 0.621070 0.100 Uiso 1 1 calc R . . . .
C13B C 0.3945(15) 0.2389(10) 0.7349(5) 0.112(5) Uani 1 1 d . . . . .
H13D H 0.409243 0.221160 0.767031 0.168 Uiso 1 1 calc GR . . . .
H13E H 0.445159 0.298304 0.727363 0.168 Uiso 1 1 calc GR . . . .
H13F H 0.416811 0.180538 0.715919 0.168 Uiso 1 1 calc GR . . . .
C14A C 0.6176(15) 1.0092(12) 0.6196(5) 0.125(5) Uani 1 1 d . . . . .
H14A H 0.704635 0.989491 0.628318 0.150 Uiso 0.63(4) 1 calc R . P A 1
H14B H 0.705603 0.995394 0.629332 0.150 Uiso 0.37(4) 1 calc R . P A 2
Cl4 Cl 0.5672(9) 0.6284(7) 0.6321(4) 0.121(3) Uiso 0.539(15) 1 d D . P B 1
Cl5 Cl 0.5490(10) 0.4719(10) 0.5568(4) 0.160(5) Uiso 0.539(15) 1 d D . P B 1
Cl6 Cl 0.6185(13) 0.4072(12) 0.6483(6) 0.203(6) Uiso 0.539(15) 1 d D . P B 1
C141 C 0.631(2) 0.5068(14) 0.6079(6) 0.121(10) Uiso 0.539(15) 1 d D . P B 1
H141 H 0.720611 0.517259 0.601307 0.145 Uiso 0.539(15) 1 calc R . P B 1
Cl2A Cl 0.605(4) 1.140(3) 0.6179(17) 0.223(18) Uani 0.37(4) 1 d . . P A 2
Cl3A Cl 0.594(4) 0.944(7) 0.575(3) 0.39(3) Uani 0.37(4) 1 d . . P A 2
Cl1A Cl 0.526(3) 0.966(4) 0.6670(19) 0.220(18) Uani 0.37(4) 1 d . . P A 2
Cl4A Cl 0.5994(13) 0.6292(10) 0.6098(6) 0.164(5) Uiso 0.461(15) 1 d D . P B 2
Cl5A Cl 0.5673(16) 0.4154(16) 0.5819(7) 0.214(7) Uiso 0.461(15) 1 d D . P B 2
Cl6A Cl 0.6123(13) 0.4527(13) 0.6754(6) 0.179(6) Uiso 0.461(15) 1 d D . P B 2
C142 C 0.529(3) 0.5045(16) 0.6260(7) 0.135(13) Uiso 0.461(15) 1 d D . P B 2
H142 H 0.438025 0.509600 0.630271 0.163 Uiso 0.461(15) 1 calc R . P B 2
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
S2A 0.102(2) 0.0550(17) 0.0551(16) 0.0015(12) -0.0007(14) 0.0042(15)
S1A 0.122(3) 0.0436(16) 0.0571(17) -0.0017(12) 0.0033(17) 0.0051(16)
S1B 0.153(3) 0.0522(18) 0.0566(18) 0.0020(13) 0.0079(19) 0.0015(19)
S2B 0.118(3) 0.119(3) 0.0578(19) 0.0088(17) 0.0152(17) 0.018(2)
O1A 0.118(6) 0.042(4) 0.059(5) 0.003(3) -0.003(4) 0.001(4)
Cl2 0.146(12) 0.148(12) 0.212(12) -0.071(11) -0.013(10) 0.008(8)
O2A 0.114(6) 0.041(4) 0.068(4) -0.001(3) -0.010(4) -0.007(4)
O1B 0.130(7) 0.054(5) 0.059(5) 0.002(4) 0.015(4) 0.002(4)
Cl3 0.156(9) 0.180(10) 0.099(7) 0.010(7) -0.004(4) -0.073(7)
N1A 0.092(7) 0.038(5) 0.065(6) -0.003(4) 0.005(5) -0.004(4)
O4A 0.173(8) 0.035(4) 0.080(5) -0.007(4) -0.013(5) -0.013(5)
Cl1 0.219(15) 0.255(17) 0.151(12) 0.079(12) -0.011(10) -0.122(14)
O2B 0.167(8) 0.067(5) 0.062(5) -0.007(4) 0.017(5) 0.024(5)
N1B 0.127(8) 0.037(5) 0.065(6) 0.001(4) 0.001(5) -0.004(5)
N2A 0.117(8) 0.041(5) 0.059(5) 0.003(4) -0.015(5) -0.001(5)
N3A 0.108(8) 0.038(5) 0.063(5) -0.002(4) -0.011(5) 0.005(5)
O3B 0.165(9) 0.088(6) 0.071(5) 0.001(5) -0.021(6) -0.026(6)
C10A 0.074(7) 0.038(6) 0.065(7) 0.000(5) 0.006(5) 0.005(5)
C6A 0.102(9) 0.040(6) 0.047(6) -0.003(5) 0.000(6) -0.005(5)
O3A 0.134(7) 0.080(6) 0.067(5) -0.006(4) 0.024(5) 0.013(5)
C9A 0.080(8) 0.051(6) 0.054(6) 0.009(5) 0.001(5) -0.001(5)
N2B 0.134(9) 0.053(6) 0.069(6) -0.006(5) 0.015(5) 0.003(6)
N3B 0.120(9) 0.033(5) 0.067(6) 0.008(4) 0.018(5) 0.010(5)
C8A 0.092(8) 0.031(5) 0.052(6) -0.006(4) 0.007(5) -0.006(5)
O4B 0.200(10) 0.037(4) 0.114(7) -0.005(4) 0.040(6) 0.010(5)
C10B 0.090(9) 0.059(7) 0.069(7) 0.015(6) 0.009(6) 0.014(6)
C2A 0.130(11) 0.034(6) 0.084(9) 0.007(6) 0.014(8) -0.001(6)
C5A 0.081(7) 0.030(5) 0.061(7) -0.001(5) -0.001(5) -0.011(5)
C3A 0.137(12) 0.028(6) 0.108(11) -0.001(6) 0.017(8) -0.004(6)
C8B 0.096(9) 0.058(7) 0.053(7) -0.008(5) 0.000(6) 0.020(6)
C7A 0.101(8) 0.035(5) 0.058(6) 0.000(5) -0.007(6) -0.012(5)
C9B 0.101(9) 0.070(8) 0.053(6) 0.007(6) 0.006(6) 0.018(7)
C11A 0.099(9) 0.049(6) 0.068(7) 0.009(6) 0.013(6) 0.003(6)
C5B 0.102(9) 0.046(7) 0.070(8) 0.000(6) 0.005(6) 0.013(6)
C12A 0.111(9) 0.044(6) 0.074(8) 0.003(5) 0.010(7) 0.007(6)
C4A 0.122(11) 0.068(8) 0.073(8) -0.005(6) -0.010(7) -0.013(7)
C6B 0.092(8) 0.045(6) 0.054(7) -0.001(5) -0.003(6) 0.002(5)
C7B 0.137(10) 0.037(6) 0.054(7) 0.005(5) 0.014(6) 0.017(6)
C4B 0.128(11) 0.045(7) 0.097(9) -0.005(6) 0.020(8) -0.004(7)
C2B 0.142(11) 0.032(6) 0.083(9) 0.000(6) 0.014(7) -0.002(6)
C11B 0.094(10) 0.108(10) 0.069(9) 0.022(8) 0.003(7) -0.008(8)
C1A 0.107(9) 0.056(7) 0.075(8) 0.024(6) 0.008(6) 0.003(6)
C13A 0.107(11) 0.058(7) 0.109(10) -0.004(6) -0.014(8) -0.019(7)
C3B 0.145(12) 0.062(8) 0.091(10) -0.009(7) 0.025(8) -0.009(8)
C12B 0.094(10) 0.109(11) 0.092(10) 0.035(8) 0.001(8) 0.001(8)
C1B 0.128(11) 0.056(7) 0.066(7) 0.003(6) -0.003(7) -0.013(7)
C13B 0.138(14) 0.076(9) 0.124(12) -0.006(8) 0.039(10) 0.007(9)
C14A 0.118(12) 0.118(13) 0.141(14) 0.032(11) 0.013(10) -0.041(10)
Cl2A 0.18(2) 0.14(2) 0.36(4) 0.11(2) 0.13(3) 0.035(15)
Cl3A 0.34(4) 0.45(7) 0.36(5) -0.25(5) 0.01(4) -0.20(5)
Cl1A 0.126(18) 0.31(4) 0.23(4) 0.07(3) 0.053(19) 0.00(2)
_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
S2A C9A 1.725(10) . ?
S2A C12A 1.726(10) . ?
S1A O4A 1.439(7) . ?
S1A N3A 1.624(9) . ?
S1A C10A 1.717(10) . ?
S1A O3A 1.413(9) . ?
S1B O3B 1.424(10) . ?
S1B N3B 1.627(10) . ?
S1B O4B 1.427(8) . ?
S1B C10B 1.716(11) . ?
S2B C9B 1.691(11) . ?
S2B C12B 1.731(15) . ?
O1A C6A 1.241(10) . ?
Cl2 C14A 1.77(2) . ?
O2A C8A 1.283(10) . ?
O1B C6B 1.222(11) . ?
Cl3 C14A 1.74(2) . ?
N1A H1A 0.8600 . ?
N1A C5A 1.353(11) . ?
N1A C1A 1.374(12) . ?
Cl1 C14A 1.68(2) . ?
O2B C8B 1.267(11) . ?
N1B H1B 0.8600 . ?
N1B C5B 1.345(13) . ?
N1B C1B 1.342(12) . ?
N2A H2A 0.8600 . ?
N2A C6A 1.395(12) . ?
N2A C5A 1.330(11) . ?
N3A C7A 1.443(12) . ?
N3A C13A 1.497(15) . ?
C10A C9A 1.361(13) . ?
C10A C11A 1.408(13) . ?
C6A C7A 1.427(13) . ?
C9A C8A 1.481(13) . ?
N2B H2B 0.8600 . ?
N2B C5B 1.334(12) . ?
N2B C6B 1.426(12) . ?
N3B C7B 1.460(12) . ?
N3B C13B 1.479(16) . ?
C8A C7A 1.396(13) . ?
C10B C9B 1.390(14) . ?
C10B C11B 1.401(15) . ?
C2A H2AA 0.9300 . ?
C2A C3A 1.379(16) . ?
C2A C1A 1.335(15) . ?
C5A C4A 1.374(14) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.380(15) . ?
C8B C9B 1.468(15) . ?
C8B C7B 1.402(14) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.371(14) . ?
C5B C4B 1.372(14) . ?
C12A H12A 0.9300 . ?
C4A H4A 0.9300 . ?
C6B C7B 1.423(13) . ?
C4B H4B 0.9300 . ?
C4B C3B 1.367(16) . ?
C2B H2BA 0.9300 . ?
C2B C3B 1.364(15) . ?
C2B C1B 1.350(14) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.322(16) . ?
C1A H1AA 0.9300 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C3B H3B 0.9300 . ?
C12B H12B 0.9300 . ?
C1B H1BA 0.9300 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A Cl2A 1.67(4) . ?
C14A Cl3A 1.54(4) . ?
C14A Cl1A 1.79(4) . ?
Cl4 C141 1.844(17) . ?
Cl5 C141 1.743(17) . ?
Cl6 C141 1.735(17) . ?
C141 H141 0.9800 . ?
Cl4A C142 1.827(18) . ?
Cl5A C142 1.764(18) . ?
Cl6A C142 1.776(18) . ?
C142 H142 0.9800 . ?
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
C9A S2A C12A 90.6(5) . . ?
O4A S1A N3A 108.5(5) . . ?
O4A S1A C10A 110.2(5) . . ?
N3A S1A C10A 101.9(4) . . ?
O3A S1A O4A 118.1(5) . . ?
O3A S1A N3A 107.8(5) . . ?
O3A S1A C10A 109.1(5) . . ?
O3B S1B N3B 108.1(5) . . ?
O3B S1B O4B 118.4(6) . . ?
O3B S1B C10B 108.1(6) . . ?
N3B S1B C10B 102.7(5) . . ?
O4B S1B N3B 108.4(6) . . ?
O4B S1B C10B 110.0(5) . . ?
C9B S2B C12B 90.5(6) . . ?
C5A N1A H1A 118.3 . . ?
C5A N1A C1A 123.4(9) . . ?
C1A N1A H1A 118.3 . . ?
C5B N1B H1B 119.0 . . ?
C1B N1B H1B 119.0 . . ?
C1B N1B C5B 121.9(9) . . ?
C6A N2A H2A 115.9 . . ?
C5A N2A H2A 115.9 . . ?
C5A N2A C6A 128.1(8) . . ?
C7A N3A S1A 115.8(7) . . ?
C7A N3A C13A 111.8(8) . . ?
C13A N3A S1A 117.4(7) . . ?
C9A C10A S1A 117.3(7) . . ?
C9A C10A C11A 112.1(9) . . ?
C11A C10A S1A 130.3(8) . . ?
O1A C6A N2A 119.5(8) . . ?
O1A C6A C7A 126.1(8) . . ?
N2A C6A C7A 114.3(9) . . ?
C10A C9A S2A 112.6(7) . . ?
C10A C9A C8A 126.5(9) . . ?
C8A C9A S2A 120.8(7) . . ?
C5B N2B H2B 116.0 . . ?
C5B N2B C6B 128.0(9) . . ?
C6B N2B H2B 116.0 . . ?
C7B N3B S1B 114.8(8) . . ?
C7B N3B C13B 115.0(10) . . ?
C13B N3B S1B 116.5(7) . . ?
O2A C8A C9A 118.3(9) . . ?
O2A C8A C7A 124.9(8) . . ?
C7A C8A C9A 116.6(8) . . ?
C9B C10B S1B 116.7(8) . . ?
C9B C10B C11B 112.3(11) . . ?
C11B C10B S1B 130.6(10) . . ?
C3A C2A H2AA 121.2 . . ?
C1A C2A H2AA 121.2 . . ?
C1A C2A C3A 117.6(10) . . ?
N1A C5A C4A 116.6(9) . . ?
N2A C5A N1A 120.7(8) . . ?
N2A C5A C4A 122.7(10) . . ?
C2A C3A H3A 119.1 . . ?
C2A C3A C4A 121.9(10) . . ?
C4A C3A H3A 119.1 . . ?
O2B C8B C9B 117.3(10) . . ?
O2B C8B C7B 124.2(10) . . ?
C7B C8B C9B 118.4(9) . . ?
C6A C7A N3A 113.8(8) . . ?
C8A C7A N3A 120.6(8) . . ?
C8A C7A C6A 125.3(8) . . ?
C10B C9B S2B 111.7(8) . . ?
C10B C9B C8B 125.5(10) . . ?
C8B C9B S2B 122.7(8) . . ?
C10A C11A H11A 123.6 . . ?
C12A C11A C10A 112.9(10) . . ?
C12A C11A H11A 123.6 . . ?
N1B C5B C4B 118.6(10) . . ?
N2B C5B N1B 119.5(9) . . ?
N2B C5B C4B 121.9(11) . . ?
S2A C12A H12A 124.1 . . ?
C11A C12A S2A 111.7(8) . . ?
C11A C12A H12A 124.1 . . ?
C5A C4A C3A 120.0(11) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
O1B C6B N2B 119.4(9) . . ?
O1B C6B C7B 127.8(9) . . ?
C7B C6B N2B 112.7(9) . . ?
C8B C7B N3B 119.1(8) . . ?
C8B C7B C6B 126.9(9) . . ?
C6B C7B N3B 113.8(9) . . ?
C5B C4B H4B 120.4 . . ?
C3B C4B C5B 119.3(12) . . ?
C3B C4B H4B 120.4 . . ?
C3B C2B H2BA 120.8 . . ?
C1B C2B H2BA 120.8 . . ?
C1B C2B C3B 118.5(11) . . ?
C10B C11B H11B 123.9 . . ?
C12B C11B C10B 112.2(13) . . ?
C12B C11B H11B 123.9 . . ?
N1A C1A H1AA 119.8 . . ?
C2A C1A N1A 120.5(11) . . ?
C2A C1A H1AA 119.8 . . ?
N3A C13A H13A 109.5 . . ?
N3A C13A H13B 109.5 . . ?
N3A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C4B C3B H3B 119.5 . . ?
C2B C3B C4B 121.0(11) . . ?
C2B C3B H3B 119.5 . . ?
S2B C12B H12B 123.3 . . ?
C11B C12B S2B 113.3(10) . . ?
C11B C12B H12B 123.3 . . ?
N1B C1B C2B 120.7(11) . . ?
N1B C1B H1BA 119.7 . . ?
C2B C1B H1BA 119.7 . . ?
N3B C13B H13D 109.5 . . ?
N3B C13B H13E 109.5 . . ?
N3B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
Cl2 C14A H14A 109.3 . . ?
Cl3 C14A Cl2 107.2(11) . . ?
Cl3 C14A H14A 109.3 . . ?
Cl1 C14A Cl2 113.6(14) . . ?
Cl1 C14A Cl3 108.1(12) . . ?
Cl1 C14A H14A 109.3 . . ?
Cl2A C14A H14B 105.4 . . ?
Cl2A C14A Cl1A 106(2) . . ?
Cl3A C14A H14B 105.4 . . ?
Cl3A C14A Cl2A 120(4) . . ?
Cl3A C14A Cl1A 113(2) . . ?
Cl1A C14A H14B 105.4 . . ?
Cl4 C141 H141 109.3 . . ?
Cl5 C141 Cl4 110.8(11) . . ?
Cl5 C141 H141 109.3 . . ?
Cl6 C141 Cl4 108.9(12) . . ?
Cl6 C141 Cl5 109.3(13) . . ?
Cl6 C141 H141 109.3 . . ?
Cl4A C142 H142 112.7 . . ?
Cl5A C142 Cl4A 105.8(14) . . ?
Cl5A C142 Cl6A 102.5(14) . . ?
Cl5A C142 H142 112.7 . . ?
Cl6A C142 Cl4A 109.5(14) . . ?
Cl6A C142 H142 112.7 . . ?
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
_geom_hbond_publ_flag
N1A H1A O1A 0.86 2.03 2.655(10) 129.3 . yes
N1A H1A O1B 0.86 2.20 2.905(11) 138.7 . yes
N1B H1B O1A 0.86 2.19 2.872(11) 136.3 . yes
N1B H1B O1B 0.86 2.00 2.645(10) 130.9 . yes
N2A H2A O2A 0.86 1.87 2.608(10) 142.3 . yes
N2B H2B O2B 0.86 1.88 2.606(11) 141.4 . yes
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
S2A C9A C8A O2A -13.2(14) . . . . ?
S2A C9A C8A C7A 171.9(8) . . . . ?
S1A N3A C7A C6A -140.0(8) . . . . ?
S1A N3A C7A C8A 45.5(13) . . . . ?
S1A C10A C9A S2A 174.1(6) . . . . ?
S1A C10A C9A C8A -3.5(15) . . . . ?
S1A C10A C11A C12A -174.4(9) . . . . ?
S1B N3B C7B C8B 47.3(13) . . . . ?
S1B N3B C7B C6B -137.0(9) . . . . ?
S1B C10B C9B S2B 175.2(6) . . . . ?
S1B C10B C9B C8B -1.5(16) . . . . ?
S1B C10B C11B C12B -174.2(10) . . . . ?
O1A C6A C7A N3A 9.4(17) . . . . ?
O1A C6A C7A C8A -176.5(11) . . . . ?
O2A C8A C7A N3A 174.7(10) . . . . ?
O2A C8A C7A C6A 0.9(18) . . . . ?
O1B C6B C7B N3B 11.9(18) . . . . ?
O1B C6B C7B C8B -172.8(12) . . . . ?
N1A C5A C4A C3A -1.0(17) . . . . ?
O4A S1A N3A C7A -167.7(7) . . . . ?
O4A S1A N3A C13A -32.1(9) . . . . ?
O4A S1A C10A C9A 146.7(9) . . . . ?
O4A S1A C10A C11A -39.3(12) . . . . ?
O2B C8B C9B S2B -11.6(15) . . . . ?
O2B C8B C9B C10B 164.7(11) . . . . ?
O2B C8B C7B N3B 171.9(11) . . . . ?
O2B C8B C7B C6B -3(2) . . . . ?
N1B C5B C4B C3B 2.0(19) . . . . ?
N2A C6A C7A N3A -170.1(9) . . . . ?
N2A C6A C7A C8A 4.1(17) . . . . ?
N2A C5A C4A C3A 178.0(11) . . . . ?
N3A S1A C10A C9A 31.7(10) . . . . ?
N3A S1A C10A C11A -154.4(10) . . . . ?
O3B S1B N3B C7B 61.0(8) . . . . ?
O3B S1B N3B C13B -160.4(9) . . . . ?
O3B S1B C10B C9B -82.7(10) . . . . ?
O3B S1B C10B C11B 89.8(12) . . . . ?
C10A S1A N3A C7A -51.5(9) . . . . ?
C10A S1A N3A C13A 84.1(8) . . . . ?
C10A C9A C8A O2A 164.1(10) . . . . ?
C10A C9A C8A C7A -10.7(16) . . . . ?
C10A C11A C12A S2A 1.2(13) . . . . ?
C6A N2A C5A N1A 9.6(17) . . . . ?
C6A N2A C5A C4A -169.4(11) . . . . ?
O3A S1A N3A C7A 63.3(8) . . . . ?
O3A S1A N3A C13A -161.1(8) . . . . ?
O3A S1A C10A C9A -82.1(9) . . . . ?
O3A S1A C10A C11A 91.8(11) . . . . ?
C9A S2A C12A C11A -1.5(9) . . . . ?
C9A C10A C11A C12A -0.2(14) . . . . ?
C9A C8A C7A N3A -10.8(15) . . . . ?
C9A C8A C7A C6A 175.4(10) . . . . ?
N2B C5B C4B C3B -178.8(12) . . . . ?
N2B C6B C7B N3B -172.3(10) . . . . ?
N2B C6B C7B C8B 3.0(17) . . . . ?
N3B S1B C10B C9B 31.3(10) . . . . ?
N3B S1B C10B C11B -156.1(11) . . . . ?
O4B S1B N3B C7B -169.5(8) . . . . ?
O4B S1B N3B C13B -30.9(10) . . . . ?
O4B S1B C10B C9B 146.5(9) . . . . ?
O4B S1B C10B C11B -40.9(13) . . . . ?
C10B S1B N3B C7B -53.1(8) . . . . ?
C10B S1B N3B C13B 85.5(9) . . . . ?
C10B C11B C12B S2B 0.9(14) . . . . ?
C2A C3A C4A C5A 1(2) . . . . ?
C5A N1A C1A C2A -1.2(17) . . . . ?
C5A N2A C6A O1A -3.7(18) . . . . ?
C5A N2A C6A C7A 175.7(10) . . . . ?
C3A C2A C1A N1A 1.3(19) . . . . ?
C9B S2B C12B C11B -0.2(11) . . . . ?
C9B C10B C11B C12B -1.4(15) . . . . ?
C9B C8B C7B N3B -11.6(17) . . . . ?
C9B C8B C7B C6B 173.4(11) . . . . ?
C11A C10A C9A S2A -1.0(12) . . . . ?
C11A C10A C9A C8A -178.5(10) . . . . ?
C5B N1B C1B C2B 1.6(19) . . . . ?
C5B N2B C6B O1B 1.0(18) . . . . ?
C5B N2B C6B C7B -175.2(12) . . . . ?
C5B C4B C3B C2B 0(2) . . . . ?
C12A S2A C9A C10A 1.4(9) . . . . ?
C12A S2A C9A C8A 179.1(9) . . . . ?
C6B N2B C5B N1B 6.7(18) . . . . ?
C6B N2B C5B C4B -172.4(12) . . . . ?
C7B C8B C9B S2B 171.6(9) . . . . ?
C7B C8B C9B C10B -12.0(18) . . . . ?
C11B C10B C9B S2B 1.3(13) . . . . ?
C11B C10B C9B C8B -175.4(11) . . . . ?
C1A N1A C5A N2A -178.1(10) . . . . ?
C1A N1A C5A C4A 1.0(16) . . . . ?
C1A C2A C3A C4A -1(2) . . . . ?
C13A N3A C7A C6A 82.0(12) . . . . ?
C13A N3A C7A C8A -92.5(12) . . . . ?
C3B C2B C1B N1B 0(2) . . . . ?
C12B S2B C9B C10B -0.6(10) . . . . ?
C12B S2B C9B C8B 176.2(10) . . . . ?
C1B N1B C5B N2B 178.1(11) . . . . ?
C1B N1B C5B C4B -2.7(18) . . . . ?
C1B C2B C3B C4B -1(2) . . . . ?
C13B N3B C7B C8B -91.9(13) . . . . ?
C13B N3B C7B C6B 83.8(12) . . . . ?
_shelx_res_file
;
TITL
tnxchcl3i.res
created by SHELXL-2017/1 at 12:40:20 on 01-Jul-2019
CELL 0.71073 10.6019 12.781 28.841 90 92.076 90
ZERR 4 0.0012 0.001 0.002 0 0.01 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O S
UNIT 112 96 24 24 32 16
DFIX 1.78 Cl4 C141 Cl6 C141 Cl5 C141 Cl5A C142 Cl4A C142 Cl6A C142
L.S. 10
PLAN 7
SIZE 0.13 0.25 0.3
TEMP 20(3)
HTAB N1A O1A
HTAB N1A O1B
HTAB N1B O1A
HTAB N1B O1B
HTAB N2A O2A
HTAB N2B O2B
BOND
BOND $H
CONF
fmap 2
acta
SHEL 40 0.84
REM
REM
REM
WGHT 0.167800 8.226900
FVAR 0.37213 0.63015 0.53904
S2A 6 0.073629 0.745890 0.384592 11.00000 0.10196 0.05498 =
0.05506 0.00145 -0.00070 0.00417
S1A 6 0.143311 0.844593 0.521889 11.00000 0.12153 0.04364 =
0.05707 -0.00174 0.00334 0.00514
S1B 6 0.159832 0.169001 0.732551 11.00000 0.15272 0.05224 =
0.05663 0.00196 0.00791 0.00147
S2B 6 0.102316 0.260699 0.868900 11.00000 0.11832 0.11936 =
0.05777 0.00875 0.01525 0.01767
O1A 5 0.251754 0.562471 0.583096 11.00000 0.11834 0.04234 =
0.05946 0.00254 -0.00343 0.00057
PART 1
CL2 3 0.594222 1.142686 0.633123 21.00000 0.14580 0.14785 =
0.21188 -0.07105 -0.01280 0.00833
PART 0
O2A 5 0.108413 0.556453 0.445607 11.00000 0.11446 0.04082 =
0.06767 -0.00083 -0.01031 -0.00670
O1B 5 0.273687 0.450030 0.675684 11.00000 0.12974 0.05385 =
0.05943 0.00154 0.01501 0.00185
PART 1
CL3 3 0.593586 0.995833 0.559994 21.00000 0.15605 0.18005 =
0.09920 0.01004 -0.00430 -0.07336
PART 0
N1A 4 0.240247 0.355020 0.584556 11.00000 0.09183 0.03821 =
0.06490 -0.00262 0.00520 -0.00358
AFIX 43
H1A 2 0.244481 0.409910 0.601789 11.00000 -1.20000
AFIX 0
O4A 5 0.212162 0.938110 0.534244 11.00000 0.17343 0.03508 =
0.08009 -0.00737 -0.01295 -0.01342
PART 1
CL1 3 0.517369 0.928009 0.645823 21.00000 0.21877 0.25474 =
0.15116 0.07851 -0.01132 -0.12189
PART 0
O2B 5 0.147990 0.451166 0.811739 11.00000 0.16668 0.06693 =
0.06160 -0.00722 0.01674 0.02374
N1B 4 0.241011 0.655147 0.673570 11.00000 0.12695 0.03745 =
0.06459 0.00149 0.00059 -0.00357
AFIX 43
H1B 2 0.251594 0.599929 0.657121 11.00000 -1.20000
AFIX 0
N2A 4 0.190158 0.462002 0.521028 11.00000 0.11699 0.04070 =
0.05873 0.00347 -0.01484 -0.00078
AFIX 43
H2A 2 0.159345 0.463808 0.493043 11.00000 -1.20000
AFIX 0
N3A 4 0.235028 0.744545 0.531392 11.00000 0.10803 0.03796 =
0.06285 -0.00219 -0.01115 0.00501
O3B 5 0.044957 0.196509 0.708466 11.00000 0.16476 0.08782 =
0.07129 0.00099 -0.02079 -0.02622
C10A 1 0.117201 0.838561 0.462846 11.00000 0.07414 0.03836 =
0.06498 -0.00007 0.00578 0.00495
C6A 1 0.213489 0.558866 0.541944 11.00000 0.10205 0.03982 =
0.04686 -0.00291 -0.00050 -0.00460
O3A 5 0.028726 0.825246 0.543928 11.00000 0.13414 0.07950 =
0.06707 -0.00551 0.02422 0.01337
C9A 1 0.115882 0.742046 0.442899 11.00000 0.07966 0.05100 =
0.05367 0.00903 0.00058 -0.00055
N2B 4 0.218836 0.549282 0.737863 11.00000 0.13415 0.05315 =
0.06877 -0.00627 0.01499 0.00294
AFIX 43
H2B 2 0.198879 0.546359 0.766471 11.00000 -1.20000
AFIX 0
N3B 4 0.259573 0.264369 0.726477 11.00000 0.12030 0.03299 =
0.06707 0.00842 0.01835 0.01017
C8A 1 0.141438 0.641137 0.466634 11.00000 0.09187 0.03138 =
0.05247 -0.00580 0.00689 -0.00638
O4B 5 0.220255 0.073551 0.720522 11.00000 0.19960 0.03740 =
0.11383 -0.00475 0.04034 0.00962
C10B 1 0.134190 0.171337 0.790947 11.00000 0.09030 0.05929 =
0.06881 0.01494 0.00917 0.01390
C2A 1 0.257402 0.171929 0.579643 11.00000 0.13016 0.03376 =
0.08398 0.00660 0.01390 -0.00145
AFIX 43
H2AA 2 0.272279 0.106764 0.593107 11.00000 -1.20000
AFIX 0
C5A 1 0.209596 0.367217 0.538945 11.00000 0.08140 0.02992 =
0.06062 -0.00143 -0.00059 -0.01109
C3A 1 0.226716 0.181601 0.532964 11.00000 0.13694 0.02817 =
0.10778 -0.00140 0.01661 -0.00417
AFIX 43
H3A 2 0.222701 0.121758 0.514626 11.00000 -1.20000
AFIX 0
C8B 1 0.172172 0.367671 0.790111 11.00000 0.09648 0.05777 =
0.05324 -0.00827 0.00024 0.01981
C7A 1 0.190701 0.646472 0.512138 11.00000 0.10080 0.03473 =
0.05774 -0.00029 -0.00651 -0.01244
C9B 1 0.141563 0.268341 0.812680 11.00000 0.10130 0.06976 =
0.05279 0.00724 0.00584 0.01758
C11A 1 0.085680 0.918014 0.430660 11.00000 0.09856 0.04908 =
0.06839 0.00914 0.01325 0.00303
AFIX 43
H11A 2 0.081844 0.988559 0.438387 11.00000 -1.20000
AFIX 0
C5B 1 0.223223 0.644765 0.719273 11.00000 0.10176 0.04649 =
0.06985 0.00046 0.00509 0.01271
C12A 1 0.061240 0.880436 0.386736 11.00000 0.11127 0.04402 =
0.07418 0.00301 0.01000 0.00684
AFIX 43
H12A 2 0.040519 0.922314 0.361213 11.00000 -1.20000
AFIX 0
C4A 1 0.201794 0.277572 0.512686 11.00000 0.12209 0.06783 =
0.07298 -0.00541 -0.00992 -0.01330
AFIX 43
H4A 2 0.179709 0.281572 0.481234 11.00000 -1.20000
AFIX 0
C6B 1 0.243174 0.451491 0.716117 11.00000 0.09209 0.04503 =
0.05370 -0.00101 -0.00289 0.00216
C7B 1 0.219714 0.364567 0.745381 11.00000 0.13732 0.03669 =
0.05408 0.00507 0.01398 0.01673
C4B 1 0.211676 0.733463 0.745572 11.00000 0.12814 0.04528 =
0.09714 -0.00541 0.01978 -0.00401
AFIX 43
H4B 2 0.201950 0.728554 0.777416 11.00000 -1.20000
AFIX 0
C2B 1 0.229380 0.837607 0.677808 11.00000 0.14176 0.03236 =
0.08259 -0.00037 0.01438 -0.00161
AFIX 43
H2BA 2 0.230223 0.902811 0.663509 11.00000 -1.20000
AFIX 0
C11B 1 0.093697 0.092438 0.820687 11.00000 0.09400 0.10804 =
0.06941 0.02203 0.00311 -0.00818
AFIX 43
H11B 2 0.081742 0.023127 0.811749 11.00000 -1.20000
AFIX 0
C1A 1 0.264971 0.259560 0.604801 11.00000 0.10683 0.05627 =
0.07454 0.02361 0.00829 0.00301
AFIX 43
H1AA 2 0.287140 0.255939 0.636255 11.00000 -1.20000
AFIX 0
C13A 1 0.373323 0.759752 0.524946 11.00000 0.10741 0.05840 =
0.10853 -0.00381 -0.01411 -0.01870
AFIX 137
H13A 2 0.390691 0.753736 0.492618 11.00000 -1.50000
H13B 2 0.419942 0.707357 0.542167 11.00000 -1.50000
H13C 2 0.398008 0.827912 0.535921 11.00000 -1.50000
AFIX 0
C3B 1 0.214627 0.829142 0.724450 11.00000 0.14515 0.06180 =
0.09101 -0.00894 0.02522 -0.00920
AFIX 43
H3B 2 0.206447 0.889411 0.742157 11.00000 -1.20000
AFIX 0
C12B 1 0.074444 0.127855 0.862911 11.00000 0.09388 0.10868 =
0.09177 0.03481 0.00074 0.00064
AFIX 43
H12B 2 0.048489 0.085576 0.887016 11.00000 -1.20000
AFIX 0
C1B 1 0.242727 0.749144 0.652889 11.00000 0.12801 0.05551 =
0.06649 0.00274 -0.00296 -0.01311
AFIX 43
H1BA 2 0.253215 0.753395 0.621070 11.00000 -1.20000
AFIX 0
C13B 1 0.394540 0.238854 0.734941 11.00000 0.13809 0.07649 =
0.12389 -0.00638 0.03888 0.00719
AFIX 137
H13D 2 0.409243 0.221160 0.767031 11.00000 -1.50000
H13E 2 0.445159 0.298304 0.727363 11.00000 -1.50000
H13F 2 0.416811 0.180538 0.715919 11.00000 -1.50000
AFIX 0
C14A 1 0.617631 1.009230 0.619639 11.00000 0.11760 0.11815 =
0.14082 0.03226 0.01260 -0.04149
PART 1
AFIX 13
H14A 2 0.704635 0.989491 0.628318 21.00000 -1.20000
AFIX 13
PART 0
PART 2
H14B 2 0.705603 0.995394 0.629332 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
CL4 3 0.567248 0.628351 0.632091 31.00000 0.12137
CL5 3 0.548956 0.471871 0.556837 31.00000 0.15951
CL6 3 0.618539 0.407242 0.648310 31.00000 0.20338
C141 1 0.631440 0.506792 0.607867 31.00000 0.12052
AFIX 13
H141 2 0.720611 0.517259 0.601307 31.00000 -1.20000
AFIX 0
PART 0
PART 2
CL2A 3 0.604511 1.139760 0.617914 -21.00000 0.17517 0.14019 =
0.36123 0.11247 0.12717 0.03461
CL3A 3 0.593599 0.943682 0.575349 -21.00000 0.34248 0.45393 =
0.36235 -0.25108 0.01104 -0.19953
CL1A 3 0.525614 0.966158 0.667033 -21.00000 0.12557 0.31184 =
0.22736 0.06630 0.05334 0.00426
CL4A 3 0.599357 0.629178 0.609847 -31.00000 0.16411
CL5A 3 0.567332 0.415446 0.581917 -31.00000 0.21394
CL6A 3 0.612251 0.452710 0.675384 -31.00000 0.17939
C142 1 0.529100 0.504493 0.625997 -31.00000 0.13548
AFIX 13
H142 2 0.438025 0.509600 0.630271 -31.00000 -1.20000
AFIX 0
HKLF 4
REM
REM R1 = 0.1163 for 2586 Fo > 4sig(Fo) and 0.2576 for all 6880 data
REM 496 parameters refined using 6 restraints
END
WGHT 0.1673 8.3093
REM Highest difference peak 0.757, deepest hole -0.590, 1-sigma level 0.094
Q1 1 0.5874 0.3735 0.6167 11.00000 0.05 0.76
Q2 1 0.5638 0.5104 0.6975 11.00000 0.05 0.72
Q3 1 0.6099 0.5749 0.5671 11.00000 0.05 0.53
Q4 1 0.5540 0.4378 0.5690 11.00000 0.05 0.51
Q5 1 0.2274 0.2525 0.6700 11.00000 0.05 0.43
Q6 1 0.5919 0.8689 0.6193 11.00000 0.05 0.40
Q7 1 0.6342 0.4182 0.6646 11.00000 0.05 0.39
;
_shelx_res_checksum 62744
_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
;
_chemical_properties_physical Heat-sensitive