# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015
#######################################################################
#
# 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_tor86
_database_code_depnum_ccdc_archive 'CCDC 1057474'
_audit_update_record
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C13 H14 N3 O2'
_chemical_formula_weight 244.27
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'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 21/c'
_space_group_name_Hall '-P 2ybc'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 8.5132(5)
_cell_length_b 21.0477(13)
_cell_length_c 7.2003(4)
_cell_angle_alpha 90
_cell_angle_beta 113.595(2)
_cell_angle_gamma 90
_cell_volume 1182.31(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9705
_cell_measurement_theta_min 2.61
_cell_measurement_theta_max 26.35
_exptl_crystal_description rod
_exptl_crystal_colour colourless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.372
_exptl_crystal_F_000 516
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.300
_exptl_crystal_size_mid 0.100
_exptl_crystal_size_min 0.070
_exptl_absorpt_coefficient_mu 0.095
_shelx_estimated_absorpt_T_min 0.972
_shelx_estimated_absorpt_T_max 0.993
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.948
_exptl_absorpt_correction_T_max 0.999
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 20966
_diffrn_reflns_av_unetI/netI 0.0227
_diffrn_reflns_av_R_equivalents 0.0491
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -26
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 2.611
_diffrn_reflns_theta_max 26.402
_diffrn_reflns_theta_full 25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total 2413
_reflns_number_gt 2209
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 2413
_refine_ls_number_parameters 172
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0502
_refine_ls_R_factor_gt 0.0463
_refine_ls_wR_factor_ref 0.1325
_refine_ls_wR_factor_gt 0.1290
_refine_ls_goodness_of_fit_ref 1.064
_refine_ls_restrained_S_all 1.064
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1S O -0.05291(15) 0.39864(6) 1.10342(19) 0.0212(3) Uani 1 1 d . . . . .
O1 O -0.14002(15) 0.44074(6) 0.41328(17) 0.0214(3) Uani 1 1 d . . . . .
N1 N 0.65814(17) 0.34047(6) 0.8202(2) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.01848(17) 0.43140(7) 0.7538(2) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.0121 0.4358 0.8722 0.020 Uiso 1 1 calc R U . . .
N3 N 0.23188(19) 0.30567(7) 0.2734(2) 0.0247(4) Uani 1 1 d . . . . .
C1 C 0.8462(2) 0.28284(8) 0.7007(3) 0.0218(4) Uani 1 1 d . . . . .
H1 H 0.8798 0.3000 0.5954 0.033 Uiso 1 1 calc R U . . .
H7 H 0.8423 0.2364 0.6925 0.033 Uiso 1 1 calc R U . . .
H8 H 0.9299 0.2959 0.8343 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6719(2) 0.30787(7) 0.6700(3) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.4972(2) 0.36109(7) 0.7943(2) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.4791(2) 0.39412(8) 0.9563(2) 0.0193(4) Uani 1 1 d . . . . .
H11 H 0.5768 0.4009 1.0788 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3226(2) 0.41634(8) 0.9381(2) 0.0189(4) Uani 1 1 d . . . . .
H12 H 0.3132 0.4387 1.0477 0.023 Uiso 1 1 calc R U . . .
C6 C 0.1743(2) 0.40646(8) 0.7578(2) 0.0164(3) Uani 1 1 d . . . . .
C7 C -0.1220(2) 0.44927(7) 0.5899(2) 0.0159(3) Uani 1 1 d . . . . .
C8 C -0.25617(19) 0.48348(7) 0.6411(2) 0.0158(3) Uani 1 1 d . . . . .
H4 H -0.2201 0.5282 0.6750 0.019 Uiso 1 1 calc R U . . .
H3 H -0.2618 0.4636 0.7628 0.019 Uiso 1 1 calc R U . . .
C9 C -0.43452(19) 0.48246(7) 0.4703(2) 0.0157(3) Uani 1 1 d . . . . .
H5 H -0.4717 0.4379 0.4361 0.019 Uiso 1 1 calc R U . . .
H6 H -0.4301 0.5027 0.3483 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1872(2) 0.37320(7) 0.6008(2) 0.0163(3) Uani 1 1 d . . . . .
H10 H 0.0874 0.3652 0.4817 0.020 Uiso 1 1 calc R U . . .
C11 C 0.3485(2) 0.35076(7) 0.6147(2) 0.0154(3) Uani 1 1 d . . . . .
C12 C 0.5321(2) 0.29559(8) 0.4856(3) 0.0190(4) Uani 1 1 d . . . . .
H9 H 0.5497 0.2722 0.3827 0.023 Uiso 1 1 calc R U . . .
C13 C 0.3693(2) 0.31707(8) 0.4522(3) 0.0175(4) Uani 1 1 d . . . . .
H1X H -0.149(4) 0.3769(13) 1.024(4) 0.047(7) Uiso 1 1 d . . . . .
H1Y H -0.078(3) 0.4146(13) 1.197(4) 0.041(7) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1S 0.0164(6) 0.0307(7) 0.0165(6) -0.0033(5) 0.0067(5) -0.0007(5)
O1 0.0183(6) 0.0295(7) 0.0164(6) -0.0010(5) 0.0070(5) 0.0046(5)
N1 0.0142(7) 0.0163(6) 0.0200(7) 0.0013(5) 0.0062(5) 0.0009(5)
N2 0.0149(7) 0.0213(7) 0.0150(7) 0.0002(5) 0.0069(5) 0.0028(5)
N3 0.0191(7) 0.0299(8) 0.0226(8) -0.0096(6) 0.0056(6) 0.0000(6)
C1 0.0175(8) 0.0217(8) 0.0271(9) -0.0031(7) 0.0098(7) 0.0014(6)
C2 0.0163(8) 0.0137(7) 0.0229(8) 0.0020(6) 0.0095(7) 0.0001(6)
C3 0.0143(7) 0.0146(7) 0.0195(8) 0.0024(6) 0.0069(6) 0.0010(6)
C4 0.0165(8) 0.0229(8) 0.0166(8) 0.0002(6) 0.0048(6) 0.0010(6)
C5 0.0178(8) 0.0226(8) 0.0163(8) -0.0013(6) 0.0068(6) 0.0022(6)
C6 0.0139(8) 0.0172(7) 0.0186(8) 0.0032(6) 0.0071(6) 0.0017(6)
C7 0.0138(7) 0.0157(7) 0.0182(8) 0.0000(6) 0.0063(6) -0.0008(6)
C8 0.0135(8) 0.0171(7) 0.0164(8) 0.0001(6) 0.0057(6) 0.0019(6)
C9 0.0139(8) 0.0163(7) 0.0168(8) 0.0005(6) 0.0062(6) 0.0017(6)
C10 0.0148(8) 0.0162(7) 0.0170(8) 0.0010(6) 0.0055(6) -0.0001(6)
C11 0.0147(7) 0.0128(7) 0.0192(8) 0.0021(6) 0.0075(6) -0.0001(6)
C12 0.0192(8) 0.0169(8) 0.0230(8) -0.0030(6) 0.0107(7) 0.0005(6)
C13 0.0165(8) 0.0150(7) 0.0212(8) -0.0005(6) 0.0077(7) -0.0013(6)
_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
O1 C7 1.232(2) . ?
N1 C2 1.325(2) . ?
N1 C3 1.377(2) . ?
N2 C7 1.354(2) . ?
N2 C6 1.416(2) . ?
N3 C13 1.370(2) . ?
C1 C2 1.505(2) . ?
C2 C12 1.407(2) . ?
C3 C4 1.418(2) . ?
C3 C11 1.418(2) . ?
C4 C5 1.368(2) . ?
C5 C6 1.418(2) . ?
C6 C10 1.371(2) . ?
C7 C8 1.515(2) . ?
C8 C9 1.524(2) . ?
C9 C9 1.533(3) 3_466 ?
C10 C11 1.417(2) . ?
C11 C13 1.439(2) . ?
C12 C13 1.384(2) . ?
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
C2 N1 C3 117.45(14) . . ?
C7 N2 C6 127.85(14) . . ?
N1 C2 C12 123.17(15) . . ?
N1 C2 C1 117.73(14) . . ?
C12 C2 C1 119.10(15) . . ?
N1 C3 C4 118.22(14) . . ?
N1 C3 C11 123.50(15) . . ?
C4 C3 C11 118.28(14) . . ?
C5 C4 C3 120.74(15) . . ?
C4 C5 C6 120.93(15) . . ?
C10 C6 N2 123.80(15) . . ?
C10 C6 C5 119.57(15) . . ?
N2 C6 C5 116.62(14) . . ?
O1 C7 N2 124.13(14) . . ?
O1 C7 C8 121.71(14) . . ?
N2 C7 C8 114.13(13) . . ?
C7 C8 C9 113.71(13) . . ?
C8 C9 C9 111.67(16) . 3_466 ?
C6 C10 C11 120.46(15) . . ?
C10 C11 C3 119.98(14) . . ?
C10 C11 C13 122.53(14) . . ?
C3 C11 C13 117.49(14) . . ?
C13 C12 C2 120.95(15) . . ?
N3 C13 C12 121.68(15) . . ?
N3 C13 C11 120.92(14) . . ?
C12 C13 C11 117.39(15) . . ?
_refine_diff_density_max 0.812
_refine_diff_density_min -0.199
_refine_diff_density_rms 0.054
_shelxl_version_number 2013-3
_shelx_res_file
;
TITL tor86 in P2(1)/c
CELL 0.71073 8.5132 21.0477 7.2003 90.000 113.595 90.000
ZERR 4.00 0.0005 0.0013 0.0004 0.000 0.002 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N O
UNIT 52 56 12 8
TEMP -173.000
omit 1 1 0
omit 0 4 1
SIZE 0.070 0.100 0.300
ACTA 50
L.S. 4
FMAP 2
PLAN 14
BOND
WGHT 0.065000 1.000000
FVAR 0.18991
O1S 4 -0.052906 0.398643 1.103422 11.00000 0.01642 0.03067 =
0.01654 -0.00333 0.00673 -0.00072
O1 4 -0.140015 0.440739 0.413276 11.00000 0.01834 0.02948 =
0.01641 -0.00102 0.00704 0.00465
N1 3 0.658144 0.340466 0.820204 11.00000 0.01419 0.01632 =
0.01998 0.00125 0.00622 0.00093
N2 3 0.018477 0.431395 0.753842 11.00000 0.01487 0.02129 =
0.01498 0.00023 0.00690 0.00280
AFIX 43
H2 2 0.012138 0.435810 0.872181 11.00000 -1.20000
AFIX 0
N3 3 0.231883 0.305666 0.273366 11.00000 0.01906 0.02988 =
0.02263 -0.00961 0.00558 0.00001
C1 1 0.846162 0.282842 0.700717 11.00000 0.01754 0.02165 =
0.02715 -0.00314 0.00983 0.00142
AFIX 137
H1 2 0.879760 0.299957 0.595388 11.00000 -1.50000
H7 2 0.842282 0.236355 0.692473 11.00000 -1.50000
H8 2 0.929930 0.295911 0.834316 11.00000 -1.50000
AFIX 0
C2 1 0.671909 0.307875 0.669967 11.00000 0.01630 0.01373 =
0.02294 0.00196 0.00951 0.00014
C3 1 0.497189 0.361090 0.794308 11.00000 0.01428 0.01458 =
0.01953 0.00241 0.00689 0.00098
C4 1 0.479112 0.394118 0.956255 11.00000 0.01647 0.02290 =
0.01664 0.00018 0.00475 0.00103
AFIX 43
H11 2 0.576770 0.400889 1.078761 11.00000 -1.20000
AFIX 0
C5 1 0.322631 0.416341 0.938067 11.00000 0.01783 0.02265 =
0.01626 -0.00134 0.00685 0.00219
AFIX 43
H12 2 0.313207 0.438710 1.047747 11.00000 -1.20000
AFIX 0
C6 1 0.174288 0.406461 0.757817 11.00000 0.01385 0.01724 =
0.01862 0.00317 0.00712 0.00175
C7 1 -0.121967 0.449270 0.589929 11.00000 0.01378 0.01574 =
0.01819 0.00002 0.00633 -0.00080
C8 1 -0.256166 0.483478 0.641054 11.00000 0.01349 0.01713 =
0.01642 0.00009 0.00565 0.00187
AFIX 23
H4 2 -0.220143 0.528208 0.674977 11.00000 -1.20000
H3 2 -0.261788 0.463580 0.762830 11.00000 -1.20000
AFIX 0
C9 1 -0.434521 0.482459 0.470349 11.00000 0.01389 0.01630 =
0.01678 0.00051 0.00616 0.00168
AFIX 23
H5 2 -0.471714 0.437850 0.436111 11.00000 -1.20000
H6 2 -0.430123 0.502654 0.348344 11.00000 -1.20000
AFIX 0
C10 1 0.187229 0.373202 0.600756 11.00000 0.01483 0.01619 =
0.01702 0.00096 0.00552 -0.00013
AFIX 43
H10 2 0.087369 0.365157 0.481747 11.00000 -1.20000
AFIX 0
C11 1 0.348488 0.350759 0.614749 11.00000 0.01469 0.01282 =
0.01922 0.00205 0.00746 -0.00010
C12 1 0.532068 0.295589 0.485631 11.00000 0.01921 0.01690 =
0.02298 -0.00299 0.01070 0.00046
AFIX 43
H9 2 0.549660 0.272216 0.382708 11.00000 -1.20000
AFIX 0
C13 1 0.369300 0.317071 0.452160 11.00000 0.01652 0.01502 =
0.02123 -0.00055 0.00769 -0.00128
H1X 2 -0.149206 0.376890 1.023970 11.00000 0.04675
H1Y 2 -0.077853 0.414640 1.196792 11.00000 0.04145
HKLF 4 1 1 0 0 0 1 0 0 0 1
REM tor86 in P2(1)/c
REM R1 = 0.0463 for 2209 Fo > 4sig(Fo) and 0.0502 for all 2413 data
REM 172 parameters refined using 0 restraints
END
WGHT 0.0634 0.9472
REM Highest difference peak 0.812, deepest hole -0.199, 1-sigma level 0.054
Q1 1 0.1390 0.3325 0.2410 11.00000 0.05 0.81
Q2 1 0.2546 0.2884 0.1786 11.00000 0.05 0.71
Q3 1 0.7597 0.2963 0.6769 11.00000 0.05 0.30
Q4 1 -0.1871 0.4659 0.6165 11.00000 0.05 0.29
Q5 1 -0.3491 0.4786 0.5629 11.00000 0.05 0.28
Q6 1 -0.5000 0.5000 0.5000 10.50000 0.05 0.26
Q7 1 0.4517 0.3191 0.4582 11.00000 0.05 0.24
Q8 1 0.2431 0.4008 0.8609 11.00000 0.05 0.23
Q9 1 0.5986 0.2985 0.5864 11.00000 0.05 0.23
Q10 1 0.2706 0.3667 0.5972 11.00000 0.05 0.22
Q11 1 0.7402 0.3539 0.9218 11.00000 0.05 0.22
Q12 1 0.4220 0.3483 0.7213 11.00000 0.05 0.20
Q13 1 0.0937 0.4229 0.7462 11.00000 0.05 0.20
Q14 1 0.3995 0.3904 0.9746 11.00000 0.05 0.19
;
_shelx_res_checksum 43063
#######################################################################
#
# 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_Tor88
_database_code_depnum_ccdc_archive 'CCDC 1057475'
_audit_update_record
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_audit_creation_date 2014-07-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number 2014-3
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C11 H10 N3 O, 2(C H4 O)'
_chemical_formula_sum 'C13 H18 N3 O3'
_chemical_formula_weight 264.30
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 6.2877(7)
_cell_length_b 8.8655(9)
_cell_length_c 12.0399(13)
_cell_angle_alpha 102.993(5)
_cell_angle_beta 91.548(6)
_cell_angle_gamma 92.630(6)
_cell_volume 652.79(12)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 8811
_cell_measurement_temperature 100
_cell_measurement_theta_max 69.439
_cell_measurement_theta_min 3.771
_shelx_estimated_absorpt_T_max 0.988
_shelx_estimated_absorpt_T_min 0.786
_exptl_absorpt_coefficient_mu 0.800
_exptl_absorpt_correction_T_max 0.7532
_exptl_absorpt_correction_T_min 0.6330
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1543 before and 0.1014 after correction.
The Ratio of minimum to maximum transmission is 0.8404.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour 'Light Yellow'
_exptl_crystal_colour_modifier Light
_exptl_crystal_colour_primary Yellow
_exptl_crystal_density_diffrn 1.345
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Needle
_exptl_crystal_F_000 282
_exptl_crystal_size_max 0.317
_exptl_crystal_size_mid 0.031
_exptl_crystal_size_min 0.015
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0331
_diffrn_reflns_av_unetI/netI 0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 20226
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full 68.000
_diffrn_reflns_theta_max 69.433
_diffrn_reflns_theta_min 3.770
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device 'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type 'Bruker X8 APEX II'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source 'Micro Focus Rotating Anode'
_diffrn_source_type 'Bruker FR-591'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2050
_reflns_number_total 2357
_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 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max 0.283
_refine_diff_density_min -0.214
_refine_diff_density_rms 0.050
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 195
_refine_ls_number_reflns 2357
_refine_ls_number_restraints 5
_refine_ls_R_factor_all 0.0490
_refine_ls_R_factor_gt 0.0427
_refine_ls_restrained_S_all 1.059
_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^)+(0.0735P)^2^+0.1982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1156
_refine_ls_wR_factor_ref 0.1203
_refine_special_details
;
?
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Restrained distances
O1S-H1S = O2S-H2S = N3-H3B = N3-H3A = N1-H1
0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
C3(H3), C4(H4), C7(H7), C9(H9)
3.b Idealised Me refined as rotating group:
C2S(H2SA,H2SB,H2SC), C11(H11A,H11B,H11C), C1S(H1SA,H1SB,H1SC)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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
O1 O 0.10028(17) 0.69310(12) 0.52600(9) 0.0278(3) Uani 1 1 d . . . . .
N1 N 0.2340(2) 0.48136(15) 0.57957(11) 0.0222(3) Uani 1 1 d D . . . .
H1 H 0.204(3) 0.3827(17) 0.5748(14) 0.018(4) Uiso 1 1 d D . . . .
N2 N 1.00360(19) 0.69099(14) 0.82095(10) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.8086(2) 0.21801(15) 0.76492(12) 0.0267(3) Uani 1 1 d D . . . .
H3A H 0.686(3) 0.178(2) 0.7278(16) 0.038(5) Uiso 1 1 d D . . . .
H3B H 0.898(3) 0.155(2) 0.7863(16) 0.033(5) Uiso 1 1 d D . . . .
C1 C 0.0931(2) 0.55645(17) 0.52900(12) 0.0211(3) Uani 1 1 d . . . . .
C2 C 0.4278(2) 0.53732(17) 0.63957(12) 0.0216(3) Uani 1 1 d . . . . .
C2S C 1.2410(3) 1.0590(2) 0.93484(16) 0.0394(5) Uani 1 1 d . . . . .
H2SA H 1.3936 1.0611 0.9202 0.059 Uiso 1 1 calc GR . . . .
H2SB H 1.2120 0.9946 0.9896 0.059 Uiso 1 1 calc GR . . . .
H2SC H 1.1989 1.1647 0.9663 0.059 Uiso 1 1 calc GR . . . .
C3 C 0.5031(2) 0.69441(17) 0.65807(13) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.4232 0.7670 0.6297 0.027 Uiso 1 1 calc R . . . .
C4 C 0.6922(2) 0.74007(17) 0.71728(13) 0.0228(3) Uani 1 1 d . . . . .
H4 H 0.7422 0.8455 0.7295 0.027 Uiso 1 1 calc R . . . .
C5 C 0.8163(2) 0.63579(17) 0.76112(12) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.7402(2) 0.47808(17) 0.74096(12) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.5443(2) 0.43275(17) 0.68061(13) 0.0216(3) Uani 1 1 d . . . . .
H7 H 0.4917 0.3279 0.6680 0.026 Uiso 1 1 calc R . . . .
C8 C 0.8689(2) 0.37115(17) 0.78270(13) 0.0226(3) Uani 1 1 d . . . . .
C9 C 1.0552(2) 0.43116(17) 0.84210(13) 0.0241(3) Uani 1 1 d . . . . .
H9 H 1.1444 0.3642 0.8711 0.029 Uiso 1 1 calc R . . . .
C10 C 1.1161(2) 0.58959(17) 0.86068(13) 0.0220(3) Uani 1 1 d . . . . .
C11 C 1.3162(3) 0.65133(18) 0.92947(14) 0.0265(4) Uani 1 1 d . . . . .
H11A H 1.3928 0.7252 0.8934 0.040 Uiso 1 1 calc GR . . . .
H11B H 1.4068 0.5655 0.9333 0.040 Uiso 1 1 calc GR . . . .
H11C H 1.2800 0.7037 1.0068 0.040 Uiso 1 1 calc GR . . . .
O1S O 0.38713(19) 0.06591(13) 0.66621(10) 0.0306(3) Uani 1 1 d D . . . .
H1S H 0.301(4) 0.035(3) 0.7144(18) 0.062(7) Uiso 1 1 d D . . . .
C1S C 0.2636(3) 0.06191(19) 0.56528(15) 0.0348(4) Uani 1 1 d . . . . .
H1SA H 0.3462 0.1119 0.5144 0.052 Uiso 1 1 calc GR . . . .
H1SB H 0.1334 0.1171 0.5848 0.052 Uiso 1 1 calc GR . . . .
H1SC H 0.2259 -0.0460 0.5269 0.052 Uiso 1 1 calc GR . . . .
O2S O 1.12319(18) 0.99618(12) 0.83126(10) 0.0278(3) Uani 1 1 d D . . . .
H2S H 1.096(4) 0.896(2) 0.825(2) 0.062(7) Uiso 1 1 d D . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0271(6) 0.0222(6) 0.0353(6) 0.0104(5) -0.0042(5) -0.0042(4)
N1 0.0218(7) 0.0188(6) 0.0263(7) 0.0064(5) 0.0001(5) -0.0024(5)
N2 0.0207(6) 0.0196(6) 0.0227(7) 0.0070(5) 0.0015(5) -0.0030(5)
N3 0.0261(7) 0.0184(6) 0.0369(8) 0.0105(6) -0.0047(6) -0.0026(5)
C1 0.0212(8) 0.0231(7) 0.0200(7) 0.0067(6) 0.0038(6) 0.0004(6)
C2 0.0221(7) 0.0213(7) 0.0217(8) 0.0059(6) 0.0042(6) -0.0018(6)
C2S 0.0484(11) 0.0270(9) 0.0415(11) 0.0085(7) -0.0127(8) -0.0073(8)
C3 0.0239(8) 0.0205(7) 0.0253(8) 0.0084(6) 0.0027(6) 0.0013(6)
C4 0.0264(8) 0.0166(7) 0.0262(8) 0.0068(6) 0.0033(6) -0.0028(6)
C5 0.0214(7) 0.0218(7) 0.0206(7) 0.0064(6) 0.0048(6) -0.0011(6)
C6 0.0223(8) 0.0205(7) 0.0212(8) 0.0054(6) 0.0052(6) -0.0027(6)
C7 0.0230(8) 0.0180(7) 0.0245(8) 0.0065(6) 0.0038(6) -0.0025(6)
C8 0.0247(8) 0.0213(7) 0.0228(8) 0.0073(6) 0.0061(6) -0.0011(6)
C9 0.0262(8) 0.0217(8) 0.0267(8) 0.0101(6) 0.0029(6) 0.0004(6)
C10 0.0226(8) 0.0241(8) 0.0205(7) 0.0075(6) 0.0037(6) -0.0013(6)
C11 0.0257(8) 0.0262(8) 0.0284(8) 0.0089(6) -0.0013(6) -0.0022(6)
O1S 0.0307(6) 0.0261(6) 0.0366(7) 0.0125(5) 0.0005(5) -0.0077(5)
C1S 0.0390(10) 0.0238(8) 0.0423(10) 0.0115(7) -0.0048(8) -0.0065(7)
O2S 0.0295(6) 0.0208(5) 0.0343(6) 0.0107(4) -0.0044(5) -0.0049(4)
_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
O1 C1 1.2189(18) . ?
N1 H1 0.874(14) . ?
N1 C1 1.344(2) . ?
N1 C2 1.410(2) . ?
N2 C5 1.3743(19) . ?
N2 C10 1.331(2) . ?
N3 H3A 0.898(15) . ?
N3 H3B 0.880(15) . ?
N3 C8 1.3603(19) . ?
C1 C1 1.547(3) 2_566 ?
C2 C3 1.417(2) . ?
C2 C7 1.374(2) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C2S O2S 1.419(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.416(2) . ?
C5 C6 1.422(2) . ?
C6 C7 1.408(2) . ?
C6 C8 1.438(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.405(2) . ?
C10 C11 1.498(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O1S H1S 0.882(17) . ?
O1S C1S 1.417(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
O2S H2S 0.881(17) . ?
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
C1 N1 H1 116.6(11) . . ?
C1 N1 C2 129.64(13) . . ?
C2 N1 H1 113.7(11) . . ?
C10 N2 C5 117.16(12) . . ?
H3A N3 H3B 119.1(19) . . ?
C8 N3 H3A 122.5(14) . . ?
C8 N3 H3B 118.3(13) . . ?
O1 C1 N1 127.96(14) . . ?
O1 C1 C1 121.71(17) . 2_566 ?
N1 C1 C1 110.33(15) . 2_566 ?
N1 C2 C3 122.46(14) . . ?
C7 C2 N1 117.33(13) . . ?
C7 C2 C3 120.20(14) . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
O2S C2S H2SA 109.5 . . ?
O2S C2S H2SB 109.5 . . ?
O2S C2S H2SC 109.5 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.09(14) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.31(13) . . ?
C5 C4 H4 118.8 . . ?
N2 C5 C4 118.85(13) . . ?
N2 C5 C6 123.05(14) . . ?
C4 C5 C6 118.10(14) . . ?
C5 C6 C8 118.18(14) . . ?
C7 C6 C5 119.04(14) . . ?
C7 C6 C8 122.78(13) . . ?
C2 C7 C6 121.25(13) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N3 C8 C6 121.57(14) . . ?
N3 C8 C9 121.54(14) . . ?
C9 C8 C6 116.88(13) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.29(14) . . ?
C10 C9 H9 119.4 . . ?
N2 C10 C9 123.40(14) . . ?
N2 C10 C11 116.99(13) . . ?
C9 C10 C11 119.60(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1S O1S H1S 106.7(16) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S O2S H2S 109.1(16) . . ?
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
N3 H3A O1S 0.898(15) 2.118(16) 3.0059(18) 169.6(19) .
N3 H3B O2S 0.880(15) 2.186(16) 3.0653(18) 177.4(18) 1_545
O1S H1S O2S 0.882(17) 1.902(17) 2.7788(16) 172(2) 1_445
O2S H2S N2 0.881(17) 1.874(17) 2.7493(16) 172(2) .
_shelx_res_file
;
TITL Tor88 in P-1 #2
CELL 1.54178 6.2877 8.8655 12.0399 102.993 91.548 92.63
ZERR 2 0.0007 0.0009 0.0013 0.0054 0.0058 0.0055
LATT 1
SFAC C H N O
UNIT 26 36 6 6
EQIV $1 +X,-1+Y,+Z
EQIV $2 -1+X,-1+Y,+Z
DFIX 0.9 O1S H1S O2S H2S N3 H3b N3 H3a N1 H1
L.S. 10
PLAN 20
SIZE 0.317 0.031 0.015
TEMP -173.15
HTAB O2S N2
HTAB N3 O2S_$1
HTAB O1S O2S_$2
HTAB N3 O1S
ACTA 136
REM Solution 1 R1 0.118 Rweak 0.004, Alpha = 0.0354 in P-1
BOND $H
fmap 2 53
REM D:/frames/guest/Tor88/Tor88.hkl
WGHT 0.073500 0.198200
FVAR 0.17836
O1 4 0.100285 0.693100 0.526001 11.00000 0.02711 0.02219 =
0.03526 0.01045 -0.00425 -0.00416
N1 3 0.233986 0.481360 0.579573 11.00000 0.02175 0.01883 =
0.02626 0.00638 0.00005 -0.00244
H1 2 0.204259 0.382740 0.574801 11.00000 0.01761
N2 3 1.003603 0.690988 0.820947 11.00000 0.02067 0.01960 =
0.02272 0.00701 0.00148 -0.00298
N3 3 0.808607 0.218011 0.764924 11.00000 0.02610 0.01839 =
0.03691 0.01052 -0.00473 -0.00258
H3A 2 0.686011 0.177767 0.727756 11.00000 0.03811
H3B 2 0.898014 0.155448 0.786269 11.00000 0.03282
C1 1 0.093111 0.556453 0.529001 11.00000 0.02119 0.02310 =
0.02001 0.00666 0.00378 0.00040
C2 1 0.427811 0.537316 0.639566 11.00000 0.02206 0.02133 =
0.02170 0.00594 0.00423 -0.00182
C2S 1 1.241037 1.059028 0.934843 11.00000 0.04839 0.02699 =
0.04153 0.00850 -0.01267 -0.00727
AFIX 137
H2SA 2 1.393573 1.061081 0.920171 11.00000 -1.50000
H2SB 2 1.211988 0.994645 0.989624 11.00000 -1.50000
H2SC 2 1.198921 1.164748 0.966252 11.00000 -1.50000
AFIX 0
C3 1 0.503121 0.694410 0.658067 11.00000 0.02390 0.02052 =
0.02531 0.00841 0.00267 0.00128
AFIX 43
H3 2 0.423215 0.766979 0.629672 11.00000 -1.20000
AFIX 0
C4 1 0.692175 0.740068 0.717284 11.00000 0.02639 0.01657 =
0.02623 0.00678 0.00331 -0.00278
AFIX 43
H4 2 0.742177 0.845476 0.729492 11.00000 -1.20000
AFIX 0
C5 1 0.816261 0.635795 0.761120 11.00000 0.02141 0.02179 =
0.02059 0.00643 0.00481 -0.00106
C6 1 0.740209 0.478081 0.740955 11.00000 0.02234 0.02051 =
0.02119 0.00539 0.00524 -0.00268
C7 1 0.544333 0.432753 0.680613 11.00000 0.02299 0.01795 =
0.02446 0.00654 0.00378 -0.00250
AFIX 43
H7 2 0.491665 0.327894 0.668017 11.00000 -1.20000
AFIX 0
C8 1 0.868884 0.371146 0.782704 11.00000 0.02472 0.02131 =
0.02282 0.00729 0.00608 -0.00105
C9 1 1.055223 0.431163 0.842101 11.00000 0.02620 0.02171 =
0.02672 0.01006 0.00291 0.00036
AFIX 43
H9 2 1.144417 0.364171 0.871108 11.00000 -1.20000
AFIX 0
C10 1 1.116138 0.589591 0.860682 11.00000 0.02257 0.02414 =
0.02049 0.00745 0.00374 -0.00134
C11 1 1.316246 0.651331 0.929472 11.00000 0.02565 0.02619 =
0.02840 0.00888 -0.00127 -0.00224
AFIX 137
H11A 2 1.392764 0.725242 0.893357 11.00000 -1.50000
H11B 2 1.406850 0.565452 0.933278 11.00000 -1.50000
H11C 2 1.279998 0.703678 1.006770 11.00000 -1.50000
AFIX 0
O1S 4 0.387127 0.065912 0.666207 11.00000 0.03067 0.02614 =
0.03659 0.01251 0.00048 -0.00766
H1S 2 0.300890 0.035321 0.714411 11.00000 0.06217
C1S 1 0.263636 0.061914 0.565281 11.00000 0.03895 0.02380 =
0.04228 0.01149 -0.00476 -0.00647
AFIX 137
H1SA 2 0.346239 0.111940 0.514375 11.00000 -1.50000
H1SB 2 0.133400 0.117082 0.584779 11.00000 -1.50000
H1SC 2 0.225861 -0.046045 0.526889 11.00000 -1.50000
AFIX 0
O2S 4 1.123188 0.996185 0.831262 11.00000 0.02950 0.02080 =
0.03430 0.01073 -0.00439 -0.00489
H2S 2 1.096287 0.896246 0.825379 11.00000 0.06247
HKLF 4
REM Tor88 in P-1 #2
REM R1 = 0.0427 for 2050 Fo > 4sig(Fo) and 0.0490 for all 2357 data
REM 195 parameters refined using 5 restraints
END
WGHT 0.0735 0.1982
REM Highest difference peak 0.283, deepest hole -0.214, 1-sigma level 0.050
Q1 1 0.7557 0.5583 0.7505 11.00000 0.05 0.28
Q2 1 1.0768 1.1374 0.8380 11.00000 0.05 0.28
Q3 1 1.0772 0.5155 0.8589 11.00000 0.05 0.26
Q4 1 1.3096 1.1473 0.9321 11.00000 0.05 0.25
Q5 1 0.6839 0.4561 0.7082 11.00000 0.05 0.23
Q6 1 1.0501 0.7583 0.8279 11.00000 0.05 0.21
Q7 1 0.7856 0.4361 0.7651 11.00000 0.05 0.21
Q8 1 0.9414 0.4249 0.8307 11.00000 0.05 0.19
Q9 1 0.4367 0.6179 0.6625 11.00000 0.05 0.18
Q10 1 0.4636 0.2912 0.6744 11.00000 0.05 0.18
Q11 1 0.4837 0.5966 0.6269 11.00000 0.05 0.18
Q12 1 0.4558 0.5003 0.6935 11.00000 0.05 0.18
Q13 1 1.3337 0.6231 0.9944 11.00000 0.05 0.17
Q14 1 0.7418 0.7010 0.7721 11.00000 0.05 0.17
Q15 1 0.1318 0.5379 0.5971 11.00000 0.05 0.17
Q16 1 0.3549 0.9054 0.6457 11.00000 0.05 0.17
Q17 1 1.0988 0.6174 0.8141 11.00000 0.05 0.17
Q18 1 1.1060 1.1392 0.9956 11.00000 0.05 0.16
Q19 1 1.2032 0.6169 0.9016 11.00000 0.05 0.16
Q20 1 0.0000 0.5000 0.5000 10.50000 0.05 0.15
;
_shelx_res_checksum 36550
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_Tor90
_database_code_depnum_ccdc_archive 'CCDC 1057476'
_audit_update_record
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_audit_creation_date 2015-02-25
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C24 H25 N6 O3, 2(H2 O), 2(Cl)'
_chemical_formula_sum 'C24 H29 Cl2 N6 O5'
_chemical_formula_weight 552.43
_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'
_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 11
_space_group_name_H-M_alt 'P 1 21/m 1'
_space_group_name_Hall '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
_cell_length_a 5.0339(9)
_cell_length_b 37.994(7)
_cell_length_c 7.1360(11)
_cell_angle_alpha 90
_cell_angle_beta 110.533(11)
_cell_angle_gamma 90
_cell_volume 1278.1(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2157
_cell_measurement_temperature 100
_cell_measurement_theta_max 26.309
_cell_measurement_theta_min 3.049
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.302
_exptl_absorpt_correction_T_max 0.0932
_exptl_absorpt_correction_T_min 0.0478
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1107 before and 0.0497 after correction. The Ratio of minimum to maximum transmission is 0.5129. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour Colorless
_exptl_crystal_colour_primary Colorless
_exptl_crystal_density_diffrn 1.435
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Plate
_exptl_crystal_F_000 578
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.08
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0438
_diffrn_reflns_av_unetI/netI 0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_k_max 45
_diffrn_reflns_limit_k_min -47
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 7858
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 26.490
_diffrn_reflns_theta_min 2.144
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device 'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type 'Bruker APEX II Ultra'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Micro Focus Rotating Anode'
_diffrn_source_type 'Bruker TXS'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2065
_reflns_number_total 2635
_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 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.380
_refine_diff_density_min -0.316
_refine_diff_density_rms 0.079
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.188
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 189
_refine_ls_number_reflns 2635
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0944
_refine_ls_R_factor_gt 0.0751
_refine_ls_restrained_S_all 1.187
_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^)+(0.0615P)^2^+2.1084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1702
_refine_ls_wR_factor_ref 0.1780
_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, All N(H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
H1SB-H1SA
1.42 with sigma of 0.02
O1S-H1SB = O1S-H1SA
0.9 with sigma of 0.02
3. Others
Fixed Sof: H1(0.5) O2S(0.5) H2SA(0.5) H2SB(0.5) Cl2(0.5)
4.a Free rotating group:
O2S(H2SA,H2SB)
4.b Secondary CH2 refined with riding coordinates:
C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
N1(H1), N3(H3), C2(H2), C6(H6), C7(H7), C9(H9)
4.d X=CH2 refined with riding coordinates:
N2(H2A,H2B)
4.e Idealised Me refined as rotating group:
C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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
O1 O -0.0495(6) 0.34083(6) 0.6330(4) 0.0267(6) Uani 1 1 d . . . . .
O2 O -0.0374(8) 0.2500 0.5089(5) 0.0240(8) Uani 1 2 d S T P . .
N1 N 0.6529(7) 0.42801(8) 0.1822(4) 0.0230(7) Uani 1 1 d . . . . .
H1 H 0.6598 0.4485 0.2416 0.028 Uiso 0.5 1 calc R . . . .
N2 N 0.6457(7) 0.33291(8) -0.0944(4) 0.0244(7) Uani 1 1 d . . . . .
H2A H 0.7277 0.3317 -0.1847 0.029 Uiso 1 1 calc R . . . .
H2B H 0.5694 0.3140 -0.0634 0.029 Uiso 1 1 calc R . . . .
N3 N 0.1346(6) 0.31437(8) 0.4167(4) 0.0224(7) Uani 1 1 d . . . . .
H3 H 0.1479 0.2940 0.3622 0.027 Uiso 1 1 calc R . . . .
C1 C 0.7677(8) 0.42501(9) 0.0389(5) 0.0240(8) Uani 1 1 d . . . . .
C2 C 0.7593(8) 0.39344(9) -0.0550(5) 0.0245(8) Uani 1 1 d . . . . .
H2 H 0.8387 0.3919 -0.1575 0.029 Uiso 1 1 calc R . . . .
C3 C 0.6371(8) 0.36329(9) -0.0049(5) 0.0214(7) Uani 1 1 d . . . . .
C4 C 0.5102(8) 0.36678(9) 0.1484(5) 0.0213(7) Uani 1 1 d . . . . .
C5 C 0.5247(7) 0.39997(9) 0.2385(5) 0.0214(7) Uani 1 1 d . . . . .
C6 C 0.4094(8) 0.40461(9) 0.3908(5) 0.0236(8) Uani 1 1 d . . . . .
H6 H 0.4215 0.4269 0.4534 0.028 Uiso 1 1 calc R . . . .
C7 C 0.2807(8) 0.37723(9) 0.4485(5) 0.0235(8) Uani 1 1 d . . . . .
H7 H 0.2025 0.3807 0.5505 0.028 Uiso 1 1 calc R . . . .
C8 C 0.2620(8) 0.34366(9) 0.3582(5) 0.0215(7) Uani 1 1 d . . . . .
C9 C 0.3782(7) 0.33886(9) 0.2103(5) 0.0208(7) Uani 1 1 d . . . . .
H9 H 0.3682 0.3164 0.1500 0.025 Uiso 1 1 calc R . . . .
C10 C 0.8974(9) 0.45761(10) -0.0095(6) 0.0307(9) Uani 1 1 d . . . . .
H10A H 0.7485 0.4750 -0.0704 0.046 Uiso 1 1 calc GR . . . .
H10B H 0.9937 0.4518 -0.1035 0.046 Uiso 1 1 calc GR . . . .
H10C H 1.0351 0.4673 0.1135 0.046 Uiso 1 1 calc GR . . . .
C11 C -0.0045(8) 0.31454(9) 0.5471(5) 0.0227(8) Uani 1 1 d . . . . .
C12 C -0.1205(8) 0.28025(9) 0.5910(5) 0.0246(8) Uani 1 1 d . . . . .
H12A H -0.0587 0.2773 0.7379 0.030 Uiso 1 1 calc R . . . .
H12B H -0.3302 0.2816 0.5389 0.030 Uiso 1 1 calc R . . . .
O1S O 0.1829(9) 0.2500 0.2070(5) 0.0291(9) Uani 1 2 d DS T P . .
H1SA H 0.001(4) 0.2500 0.130(7) 0.044 Uiso 1 2 d DRS T P . .
H1SB H 0.280(9) 0.2500 0.124(7) 0.044 Uiso 1 2 d DRS T P . .
O2S O 0.670(5) 0.4949(5) 0.337(2) 0.043(4) Uani 0.5 1 d . . . . .
H2SA H 0.5485 0.4965 0.3982 0.065 Uiso 0.5 1 d G . . . .
H2SB H 0.8401 0.4930 0.4243 0.065 Uiso 0.5 1 d G . . . .
Cl1 Cl 0.5392(3) 0.2500 -0.05830(19) 0.0262(3) Uani 1 2 d S T P . .
Cl2 Cl 0.6975(17) 0.50040(19) 0.3940(10) 0.0389(10) Uani 0.5 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0336(16) 0.0266(13) 0.0275(14) -0.0019(11) 0.0202(13) -0.0002(11)
O2 0.028(2) 0.0267(18) 0.0251(19) 0.000 0.0197(17) 0.000
N1 0.0257(17) 0.0224(15) 0.0242(16) 0.0003(12) 0.0129(14) 0.0009(13)
N2 0.0302(18) 0.0239(15) 0.0281(16) -0.0009(12) 0.0215(15) -0.0007(13)
N3 0.0256(17) 0.0239(15) 0.0231(15) -0.0016(12) 0.0153(14) -0.0006(13)
C1 0.025(2) 0.0263(18) 0.0237(18) 0.0038(14) 0.0114(16) 0.0016(16)
C2 0.028(2) 0.0284(19) 0.0228(18) 0.0022(15) 0.0161(17) 0.0000(16)
C3 0.0208(18) 0.0243(17) 0.0204(17) -0.0001(14) 0.0088(15) 0.0015(15)
C4 0.0220(19) 0.0247(17) 0.0193(17) 0.0009(14) 0.0101(16) 0.0024(15)
C5 0.0190(18) 0.0253(17) 0.0221(18) 0.0021(14) 0.0099(16) 0.0000(15)
C6 0.0244(19) 0.0261(18) 0.0224(18) -0.0031(14) 0.0107(16) 0.0017(15)
C7 0.024(2) 0.0298(19) 0.0216(18) -0.0014(14) 0.0139(16) 0.0027(16)
C8 0.0200(19) 0.0264(18) 0.0201(17) 0.0007(14) 0.0096(15) -0.0010(15)
C9 0.0170(18) 0.0248(17) 0.0220(17) -0.0004(14) 0.0084(15) 0.0016(14)
C10 0.036(2) 0.0272(19) 0.036(2) 0.0022(16) 0.021(2) -0.0021(17)
C11 0.0211(19) 0.0298(19) 0.0196(17) 0.0037(14) 0.0103(16) 0.0046(15)
C12 0.029(2) 0.0263(19) 0.0259(18) 0.0000(15) 0.0187(17) 0.0047(16)
O1S 0.038(2) 0.032(2) 0.027(2) 0.000 0.0225(19) 0.000
O2S 0.031(5) 0.048(9) 0.045(9) -0.002(6) 0.006(7) 0.002(5)
Cl1 0.0305(7) 0.0255(6) 0.0300(7) 0.000 0.0197(6) 0.000
Cl2 0.038(2) 0.0356(17) 0.048(3) -0.0090(18) 0.022(2) -0.0008(14)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.233(4) . ?
O2 C12 1.418(4) 4_565 ?
O2 C12 1.418(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.344(4) . ?
N1 C5 1.377(4) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C3 1.327(4) . ?
N3 H3 0.8800 . ?
N3 C8 1.419(4) . ?
N3 C11 1.346(4) . ?
C1 C2 1.367(5) . ?
C1 C10 1.496(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.405(5) . ?
C3 C4 1.454(5) . ?
C4 C5 1.406(5) . ?
C4 C9 1.402(5) . ?
C5 C6 1.411(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.363(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.417(5) . ?
C8 C9 1.387(5) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.505(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1S H1SA 0.888(19) . ?
O1S H1SB 0.892(19) . ?
O2S H2SA 0.8699 . ?
O2S H2SB 0.8693 . ?
Cl2 H2SA 0.7749 . ?
Cl2 H2SB 0.7299 . ?
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
C12 O2 C12 108.3(3) . 4_565 ?
C1 N1 H1 119.1 . . ?
C1 N1 C5 121.8(3) . . ?
C5 N1 H1 119.1 . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
C8 N3 H3 116.6 . . ?
C11 N3 H3 116.6 . . ?
C11 N3 C8 126.7(3) . . ?
N1 C1 C2 120.0(3) . . ?
N1 C1 C10 116.4(3) . . ?
C2 C1 C10 123.6(3) . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.1(3) . . ?
C3 C2 H2 118.9 . . ?
N2 C3 C2 119.7(3) . . ?
N2 C3 C4 122.6(3) . . ?
C2 C3 C4 117.7(3) . . ?
C5 C4 C3 117.4(3) . . ?
C9 C4 C3 123.3(3) . . ?
C9 C4 C5 119.3(3) . . ?
N1 C5 C4 121.0(3) . . ?
N1 C5 C6 119.3(3) . . ?
C4 C5 C6 119.6(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 N3 122.5(3) . . ?
C9 C8 N3 118.4(3) . . ?
C9 C8 C7 119.1(3) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 N3 125.3(3) . . ?
O1 C11 C12 116.4(3) . . ?
N3 C11 C12 118.2(3) . . ?
O2 C12 C11 115.1(3) . . ?
O2 C12 H12A 108.5 . . ?
O2 C12 H12B 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
H1SA O1S H1SB 106(3) . . ?
H2SA O2S H2SB 109.4 . . ?
H2SA Cl2 H2SB 141.3 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2S 0.88 1.88 2.759(17) 172.6 .
N1 H1 Cl2 0.88 2.23 3.108(6) 177.5 .
N2 H2A O1 0.88 2.02 2.885(4) 166.0 1_654
N3 H3 O1S 0.88 2.05 2.922(3) 173.0 .
O1S H1SA Cl1 0.888(19) 2.24(2) 3.128(4) 179(5) 1_455
O1S H1SB Cl1 0.892(19) 2.140(19) 3.030(4) 176(5) .
O2S H2SA Cl2 0.87 2.24 3.104(13) 169.9 3_666
O2S H2SB Cl2 0.87 2.25 3.095(14) 165.3 3_766
_shelx_res_file
;
tor90.res created by SHELXL-2014/7
TITL Tor90 in P21/m #11
REM SHELXT solution in P2(1)/m
REM R1 0.166, Rweak 0.026, Alpha 0.037, Orientation as input
REM Formula found by SHELXT: C24 N4 O6 Cl3
CELL 0.71073 5.0339 37.9939 7.136 90 110.533 90
ZERR 2 0.0009 0.0069 0.0011 0 0.011 0
LATT 1
SYMM -X,0.5+Y,-Z
SFAC C H Cl N O
UNIT 48 58 4 12 10
EQIV $1 1+X,+Y,-1+Z
EQIV $2 1-X,1-Y,1-Z
EQIV $3 2-X,1-Y,1-Z
EQIV $4 -1+X,+Y,+Z
DFIX 1.42 H1Sb H1Sa
DFIX 0.9 O1S H1Sb O1S H1Sa
L.S. 10
PLAN -29
TEMP -173.15
HTAB N1 O2S
HTAB N2 O1_$1
HTAB N3 O1S
HTAB O2S Cl2_$2
HTAB O2S Cl2_$3
HTAB N1 Cl2
HTAB O1S Cl1_$4
HTAB O1S Cl1
FREE O2S Cl2
FREE Cl2 H2Sb
FREE Cl2 H2Sa
BOND $H
ACTA 50
fmap 2 53
OMIT 2 3 2
OMIT 0 2 0
REM
REM
REM
WGHT 0.061500 2.108400
FVAR 0.49959
O1 5 -0.049524 0.340827 0.632959 11.00000 0.03359 0.02660 =
0.02745 -0.00194 0.02018 -0.00016
O2 5 -0.037376 0.250000 0.508934 10.50000 0.02845 0.02669 =
0.02514 0.00000 0.01970 0.00000
N1 4 0.652878 0.428012 0.182164 11.00000 0.02572 0.02242 =
0.02424 0.00032 0.01289 0.00087
AFIX 43
H1 2 0.659840 0.448463 0.241590 10.50000 -1.20000
AFIX 0
N2 4 0.645674 0.332910 -0.094412 11.00000 0.03020 0.02392 =
0.02810 -0.00086 0.02145 -0.00065
AFIX 93
H2A 2 0.727675 0.331715 -0.184723 11.00000 -1.20000
H2B 2 0.569357 0.313960 -0.063434 11.00000 -1.20000
AFIX 0
N3 4 0.134632 0.314368 0.416746 11.00000 0.02561 0.02386 =
0.02306 -0.00159 0.01531 -0.00056
AFIX 43
H3 2 0.147872 0.293975 0.362219 11.00000 -1.20000
AFIX 0
C1 1 0.767696 0.425012 0.038877 11.00000 0.02450 0.02632 =
0.02366 0.00383 0.01141 0.00165
C2 1 0.759299 0.393444 -0.055033 11.00000 0.02801 0.02836 =
0.02283 0.00221 0.01612 0.00005
AFIX 43
H2 2 0.838672 0.391855 -0.157468 11.00000 -1.20000
AFIX 0
C3 1 0.637103 0.363286 -0.004946 11.00000 0.02075 0.02426 =
0.02039 -0.00007 0.00878 0.00148
C4 1 0.510232 0.366776 0.148447 11.00000 0.02203 0.02471 =
0.01933 0.00095 0.01007 0.00241
C5 1 0.524718 0.399968 0.238469 11.00000 0.01900 0.02531 =
0.02205 0.00205 0.00988 0.00003
C6 1 0.409370 0.404610 0.390778 11.00000 0.02444 0.02606 =
0.02237 -0.00307 0.01069 0.00169
AFIX 43
H6 2 0.421487 0.426918 0.453365 11.00000 -1.20000
AFIX 0
C7 1 0.280657 0.377234 0.448511 11.00000 0.02387 0.02984 =
0.02159 -0.00142 0.01392 0.00273
AFIX 43
H7 2 0.202519 0.380702 0.550495 11.00000 -1.20000
AFIX 0
C8 1 0.262035 0.343661 0.358179 11.00000 0.01997 0.02635 =
0.02014 0.00066 0.00963 -0.00101
C9 1 0.378188 0.338864 0.210251 11.00000 0.01702 0.02478 =
0.02196 -0.00036 0.00842 0.00160
AFIX 43
H9 2 0.368193 0.316374 0.149974 11.00000 -1.20000
AFIX 0
C10 1 0.897420 0.457607 -0.009535 11.00000 0.03555 0.02721 =
0.03616 0.00215 0.02096 -0.00206
AFIX 137
H10A 2 0.748480 0.475030 -0.070351 11.00000 -1.50000
H10B 2 0.993688 0.451833 -0.103489 11.00000 -1.50000
H10C 2 1.035078 0.467312 0.113520 11.00000 -1.50000
AFIX 0
C11 1 -0.004451 0.314544 0.547139 11.00000 0.02107 0.02979 =
0.01964 0.00369 0.01029 0.00459
C12 1 -0.120483 0.280252 0.590994 11.00000 0.02897 0.02633 =
0.02587 -0.00004 0.01872 0.00468
AFIX 23
H12A 2 -0.058718 0.277310 0.737946 11.00000 -1.20000
H12B 2 -0.330206 0.281609 0.538907 11.00000 -1.20000
AFIX 0
O1S 5 0.182907 0.250000 0.206998 10.50000 0.03788 0.03185 =
0.02667 0.00000 0.02251 0.00000
H1SA 2 0.000792 0.250000 0.130114 10.50000 -1.50000
H1SB 2 0.280174 0.250000 0.123859 10.50000 -1.50000
AFIX 6
O2S 5 0.669727 0.494876 0.336700 10.50000 0.03096 0.04817 =
0.04511 -0.00193 0.00607 0.00152
H2SA 2 0.548514 0.496540 0.398195 10.50000 -1.50000
H2SB 2 0.840129 0.492977 0.424328 10.50000 -1.50000
AFIX 0
CL1 3 0.539156 0.250000 -0.058298 10.50000 0.03046 0.02554 =
0.02996 0.00000 0.01973 0.00000
CL2 3 0.697514 0.500398 0.394043 10.50000 0.03806 0.03561 =
0.04808 -0.00904 0.02157 -0.00079
HKLF 4
REM Tor90 in P21/m #11
REM R1 = 0.0751 for 2065 Fo > 4sig(Fo) and 0.0944 for all 2635 data
REM 189 parameters refined using 3 restraints
END
WGHT 0.0615 2.1083
REM Highest difference peak 0.380, deepest hole -0.316, 1-sigma level 0.079
Q1 1 -0.2590 0.2500 0.0284 10.50000 0.05 0.38
Q2 1 0.5498 0.3603 0.0627 11.00000 0.05 0.33
Q3 1 0.1324 0.2500 0.5685 10.50000 0.05 0.33
Q4 1 0.3018 0.2817 0.2074 11.00000 0.05 0.31
Q5 1 0.1897 0.2500 0.3201 10.50000 0.05 0.31
Q6 1 -0.6408 0.2500 -0.1334 10.50000 0.05 0.29
Q7 1 0.6539 0.5266 0.3359 11.00000 0.05 0.29
Q8 1 0.6286 0.3793 -0.0774 11.00000 0.05 0.29
Q9 1 0.7694 0.4405 0.2805 11.00000 0.05 0.28
Q10 1 0.5401 0.2774 0.0317 11.00000 0.05 0.28
Q11 1 -0.2995 0.2812 0.7963 11.00000 0.05 0.28
Q12 1 0.3185 0.2174 -0.0797 11.00000 0.05 0.28
Q13 1 0.4182 0.3001 0.1324 11.00000 0.05 0.28
Q14 1 0.9479 0.4817 0.1018 11.00000 0.05 0.27
Q15 1 0.2016 0.3588 0.3774 11.00000 0.05 0.27
Q16 1 0.2017 0.3396 0.1378 11.00000 0.05 0.27
Q17 1 0.6246 0.2982 -0.0618 11.00000 0.05 0.26
Q18 1 0.6797 0.4610 0.3691 11.00000 0.05 0.25
Q19 1 -0.2422 0.2500 0.4493 10.50000 0.05 0.25
Q20 1 0.5925 0.5351 0.3976 11.00000 0.05 0.25
Q21 1 0.6882 0.2860 -0.0573 11.00000 0.05 0.24
Q22 1 0.2949 0.3368 0.2877 11.00000 0.05 0.23
Q23 1 -0.0002 0.3009 0.6013 11.00000 0.05 0.22
Q24 1 0.8878 0.4389 0.0521 11.00000 0.05 0.21
Q25 1 1.1999 0.4609 0.0769 11.00000 0.05 0.21
Q26 1 1.0701 0.4578 0.0651 11.00000 0.05 0.21
Q27 1 0.6079 0.2500 -0.1450 10.50000 0.05 0.20
Q28 1 0.0893 0.2814 0.0948 11.00000 0.05 0.20
Q29 1 0.9398 0.4571 0.3688 11.00000 0.05 0.20
;
_shelx_res_checksum 28300
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_Tor99
_database_code_depnum_ccdc_archive 'CCDC 1057477'
_audit_update_record
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_audit_creation_date 2015-02-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C2 F3 O2, C21 H22 N6 O, 0.5(C6 H8 F9 Na O12)'
_chemical_formula_sum 'C26 H26 F7.50 N6 Na0.50 O9'
_chemical_formula_weight 720.52
_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'
F F 0.0171 0.0103 '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'
Na Na 0.0362 0.0249 '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'
_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 12
_space_group_name_H-M_alt 'C 1 2/m 1'
_space_group_name_Hall '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
_cell_length_a 14.0292(11)
_cell_length_b 22.3313(16)
_cell_length_c 9.5059(10)
_cell_angle_alpha 90
_cell_angle_beta 92.950(2)
_cell_angle_gamma 90
_cell_volume 2974.2(4)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2458
_cell_measurement_temperature 100
_cell_measurement_theta_max 20.707
_cell_measurement_theta_min 2.688
_shelx_estimated_absorpt_T_max 0.997
_shelx_estimated_absorpt_T_min 0.992
_exptl_absorpt_coefficient_mu 0.157
_exptl_absorpt_correction_T_max 0.0917
_exptl_absorpt_correction_T_min 0.0617
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0788 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.6728.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour Colorless
_exptl_crystal_colour_primary Colorless
_exptl_crystal_density_diffrn 1.609
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description Block
_exptl_crystal_F_000 1476
_exptl_crystal_size_max 0.053
_exptl_crystal_size_mid 0.021
_exptl_crystal_size_min 0.016
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0924
_diffrn_reflns_av_unetI/netI 0.0739
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_k_min -26
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 20193
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 25.356
_diffrn_reflns_theta_min 1.716
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type 'Bruker APEX II Ultra'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Micro Focus Rotating Anode'
_diffrn_source_type 'Bruker TXS'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1478
_reflns_number_total 2807
_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 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max 0.891
_refine_diff_density_min -0.599
_refine_diff_density_rms 0.100
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.041
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 298
_refine_ls_number_reflns 2807
_refine_ls_number_restraints 99
_refine_ls_R_factor_all 0.1943
_refine_ls_R_factor_gt 0.1119
_refine_ls_restrained_S_all 1.069
_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^)+(0.1409P)^2^+31.2725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2863
_refine_ls_wR_factor_ref 0.3458
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups, All N(H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
F1A, F2A, F3A, C2A
with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
F4A, F5A, F6A, O2A, O3A, C3A, C4A
with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
F7A, F8A, F9A, O4A, C5A, C6A
with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
Fixed Sof: F1A(0.5) F2A(0.5) F3A(0.5) F4A(0.5) F5A(0.5) F6A(0.5) O3A(0.5)
C3A(0.5) C4A(0.25) F7A(0.25) F8A(0.25) F9A(0.25) C6A(0.25)
4.a Rotating group:
O1S(H1SA,H1SB)
4.b Aromatic/amide H refined with riding coordinates:
N1(H1), N3(H3), C2(H2), C6(H6), C7(H7), C9(H9)
4.c X=CH2 refined with riding coordinates:
N2(H2A,H2B)
4.d Idealised Me refined as rotating group:
C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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
F1A F 0.0404(8) 0.4640(5) 0.6264(15) 0.083(3) Uani 0.5 1 d . U . . .
F2A F 0.0713(8) 0.4660(5) 0.8396(14) 0.083(3) Uani 0.5 1 d . U . . .
F3A F 0.0513(8) 0.5494(5) 0.7296(18) 0.081(3) Uani 0.5 1 d . U . . .
O1 O 0.0000 0.6570(3) 0.0000 0.0512(19) Uani 1 2 d S T P . .
O1A O 0.2326(4) 0.5500(2) 0.6830(5) 0.0519(14) Uani 1 1 d . . . . .
N1 N 0.1714(4) 0.6666(3) 0.6409(6) 0.0393(14) Uani 1 1 d . . . . .
H1 H 0.1819 0.6280 0.6538 0.047 Uiso 1 1 calc R . . . .
N2 N 0.1256(4) 0.8471(3) 0.5858(6) 0.0478(16) Uani 1 1 d . . . . .
H2A H 0.1362 0.8714 0.6578 0.057 Uiso 1 1 calc R . . . .
H2B H 0.1054 0.8615 0.5034 0.057 Uiso 1 1 calc R . . . .
N3 N 0.0357(4) 0.7460(3) 0.1111(5) 0.0372(14) Uani 1 1 d . . . . .
H3 H 0.0369 0.7850 0.0978 0.045 Uiso 1 1 calc R . . . .
C1 C 0.1879(4) 0.7048(3) 0.7500(7) 0.0369(16) Uani 1 1 d . . . . .
C1A C 0.1943(7) 0.5000 0.6925(10) 0.040(2) Uani 1 2 d S T P . .
C2 C 0.1724(4) 0.7647(3) 0.7315(7) 0.0387(17) Uani 1 1 d . . . . .
H2 H 0.1839 0.7909 0.8092 0.046 Uiso 1 1 calc R . . . .
C2A C 0.0904(8) 0.5000 0.7225(14) 0.060(2) Uani 1 2 d S TU P . .
C3 C 0.1402(4) 0.7887(3) 0.6015(7) 0.0396(17) Uani 1 1 d . . . . .
C4 C 0.1221(4) 0.7475(3) 0.4858(7) 0.0344(15) Uani 1 1 d . . . . .
C5 C 0.1384(4) 0.6867(3) 0.5099(7) 0.0385(16) Uani 1 1 d . . . . .
C6 C 0.1217(5) 0.6446(3) 0.4016(7) 0.0423(17) Uani 1 1 d . . . . .
H6 H 0.1332 0.6033 0.4193 0.051 Uiso 1 1 calc R . . . .
C7 C 0.0888(5) 0.6632(3) 0.2699(7) 0.0416(17) Uani 1 1 d . . . . .
H7 H 0.0784 0.6347 0.1963 0.050 Uiso 1 1 calc R . . . .
C8 C 0.0703(4) 0.7244(3) 0.2441(7) 0.0378(16) Uani 1 1 d . . . . .
C9 C 0.0868(4) 0.7658(3) 0.3502(7) 0.0364(16) Uani 1 1 d . . . . .
H9 H 0.0745 0.8070 0.3323 0.044 Uiso 1 1 calc R . . . .
C10 C 0.2241(5) 0.6764(3) 0.8856(7) 0.0438(18) Uani 1 1 d . . . . .
H10A H 0.1935 0.6373 0.8962 0.066 Uiso 1 1 calc GR . . . .
H10B H 0.2089 0.7022 0.9647 0.066 Uiso 1 1 calc GR . . . .
H10C H 0.2934 0.6711 0.8845 0.066 Uiso 1 1 calc GR . . . .
C11 C 0.0000 0.7109(6) 0.0000 0.041(2) Uani 1 2 d S T P . .
Na1 Na 0.5000 0.5000 0.5000 0.0530(16) Uani 1 4 d S T P . .
F4A F 0.2445(16) 0.5604(7) 0.1398(19) 0.158(6) Uani 0.5 1 d . U . . .
F5A F 0.2363(15) 0.4804(7) 0.0242(18) 0.174(6) Uani 0.5 1 d . U . . .
F6A F 0.1866(16) 0.4792(7) 0.198(2) 0.176(6) Uani 0.5 1 d . U . . .
O1S O 0.4220(4) 0.5756(2) 0.6421(6) 0.0536(14) Uani 1 1 d . . . . .
H1SA H 0.4565 0.5845 0.7290 0.080 Uiso 1 1 d GR . . . .
H1SB H 0.3598 0.5638 0.6677 0.080 Uiso 1 1 d GR . . . .
O2A O 0.3642(9) 0.5000 0.3345(12) 0.109(3) Uani 1 2 d S TU P . .
O3A O 0.3637(18) 0.4295(8) 0.1987(15) 0.148(6) Uani 0.5 1 d . U . . .
C3A C 0.326(3) 0.4786(12) 0.237(3) 0.152(6) Uani 0.5 1 d . U . . .
C4A C 0.258(5) 0.5000 0.152(6) 0.159(5) Uani 0.5 2 d S TU P . .
F7A F 0.442(2) 0.5155(11) 0.911(3) 0.110(7) Uani 0.25 1 d . U . . .
F8A F 0.622(2) 0.5503(13) 0.970(3) 0.127(7) Uani 0.25 1 d . U . . .
F9A F 0.505(2) 0.5148(10) 0.892(3) 0.101(6) Uani 0.25 1 d . U . . .
O4A O 0.5000(10) 0.6304(4) 0.8796(9) 0.154(4) Uani 1 1 d . U . . .
C5A C 0.5000 0.6160(6) 1.0000 0.081(4) Uani 1 2 d S TU P . .
C6A C 0.521(4) 0.5442(16) 1.003(9) 0.099(5) Uani 0.25 1 d . U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1A 0.057(6) 0.083(5) 0.107(7) -0.013(4) -0.006(5) -0.009(4)
F2A 0.062(6) 0.086(6) 0.101(6) 0.018(4) 0.006(5) -0.001(4)
F3A 0.055(6) 0.056(4) 0.132(9) 0.001(3) 0.011(6) 0.003(3)
O1 0.071(5) 0.046(5) 0.035(4) 0.000 -0.014(3) 0.000
O1A 0.052(3) 0.052(3) 0.052(3) -0.003(2) -0.003(2) -0.006(3)
N1 0.036(3) 0.045(3) 0.036(3) 0.000(3) -0.009(2) -0.004(3)
N2 0.045(3) 0.056(4) 0.041(3) -0.010(3) -0.014(3) 0.006(3)
N3 0.033(3) 0.047(3) 0.031(3) 0.003(3) -0.005(2) 0.002(3)
C1 0.025(3) 0.055(5) 0.031(4) 0.000(3) 0.000(3) -0.002(3)
C1A 0.046(6) 0.039(6) 0.034(5) 0.000 -0.010(4) 0.000
C2 0.026(3) 0.055(5) 0.035(4) -0.006(3) -0.001(3) 0.002(3)
C2A 0.044(5) 0.052(4) 0.085(6) 0.000 -0.001(4) 0.000
C3 0.020(3) 0.054(5) 0.045(4) -0.002(3) -0.002(3) 0.004(3)
C4 0.025(3) 0.044(4) 0.033(4) -0.005(3) 0.000(3) 0.001(3)
C5 0.027(3) 0.054(5) 0.034(4) 0.000(3) -0.004(3) -0.005(3)
C6 0.042(4) 0.046(4) 0.039(4) -0.006(3) -0.005(3) -0.006(3)
C7 0.042(4) 0.047(4) 0.035(4) -0.006(3) -0.005(3) -0.006(3)
C8 0.025(3) 0.054(4) 0.034(4) -0.001(3) -0.001(3) 0.001(3)
C9 0.025(3) 0.048(4) 0.036(4) 0.001(3) -0.002(3) 0.003(3)
C10 0.043(4) 0.058(5) 0.030(4) 0.001(3) -0.006(3) -0.005(3)
C11 0.023(5) 0.077(8) 0.022(5) 0.000 0.004(4) 0.000
Na1 0.057(4) 0.040(3) 0.062(4) 0.000 0.005(3) 0.000
F4A 0.233(13) 0.099(8) 0.133(10) 0.000(4) -0.077(9) 0.014(4)
F5A 0.255(12) 0.114(11) 0.142(7) -0.012(4) -0.103(8) 0.016(7)
F6A 0.247(11) 0.111(11) 0.159(9) 0.002(5) -0.089(8) -0.002(5)
O1S 0.058(3) 0.038(3) 0.064(3) -0.005(2) -0.006(3) -0.009(2)
O2A 0.121(8) 0.130(8) 0.074(6) 0.000 -0.013(5) 0.000
O3A 0.284(16) 0.100(7) 0.054(7) 0.026(5) -0.047(8) 0.031(8)
C3A 0.233(11) 0.104(8) 0.111(8) -0.005(5) -0.079(7) 0.014(5)
C4A 0.240(11) 0.090(8) 0.135(8) 0.000 -0.098(7) 0.000
F7A 0.139(12) 0.067(11) 0.119(12) -0.021(8) -0.034(10) 0.000(6)
F8A 0.135(11) 0.091(10) 0.152(16) -0.033(10) -0.027(9) 0.001(5)
F9A 0.140(12) 0.057(10) 0.102(9) -0.006(6) -0.036(10) 0.004(6)
O4A 0.290(13) 0.079(5) 0.089(5) 0.006(3) -0.042(6) -0.018(6)
C5A 0.108(9) 0.057(6) 0.073(6) 0.000 -0.039(6) 0.000
C6A 0.135(11) 0.059(6) 0.098(8) -0.004(4) -0.034(9) 0.001(4)
_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
F1A F1A 1.61(2) 6_565 ?
F1A F3A 1.031(15) 6_565 ?
F1A C2A 1.381(15) . ?
F2A F2A 1.52(2) 6_565 ?
F2A F3A 1.123(16) 6_565 ?
F2A C2A 1.385(15) . ?
F3A F1A 1.031(15) 6_565 ?
F3A F2A 1.123(16) 6_565 ?
F3A C2A 1.235(12) . ?
O1 C11 1.205(13) . ?
O1A C1A 1.245(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.353(8) . ?
N1 C5 1.381(8) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C3 1.328(9) . ?
N3 H3 0.8800 . ?
N3 C8 1.416(8) . ?
N3 C11 1.387(9) . ?
C1 C2 1.365(10) . ?
C1 C10 1.501(9) . ?
C1A O1A 1.245(7) 6_565 ?
C1A C2A 1.500(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(9) . ?
C2A F1A 1.381(15) 6_565 ?
C2A F2A 1.385(15) 6_565 ?
C2A F3A 1.235(12) 6_565 ?
C3 C4 1.447(9) . ?
C4 C5 1.394(10) . ?
C4 C9 1.416(9) . ?
C5 C6 1.405(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.410(10) . ?
C8 C9 1.380(9) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N3 1.387(9) 2 ?
Na1 O1S 2.455(5) . ?
Na1 O1S 2.455(5) 2_656 ?
Na1 O1S 2.455(5) 5_666 ?
Na1 O1S 2.455(5) 6_565 ?
Na1 O2A 2.407(12) . ?
Na1 O2A 2.407(12) 5_666 ?
F4A F5A 1.43(2) 6_565 ?
F4A F6A 1.34(3) 6_565 ?
F4A O3A 1.75(3) 6_565 ?
F4A C3A 1.68(3) 6_565 ?
F4A C4A 1.368(18) . ?
F5A F4A 1.43(2) 6_565 ?
F5A F5A 0.88(3) 6_565 ?
F5A C4A 1.32(5) . ?
F6A F4A 1.34(3) 6_565 ?
F6A F6A 0.93(3) 6_565 ?
F6A C4A 1.21(7) . ?
O1S H1SA 0.9569 . ?
O1S H1SB 0.9548 . ?
O2A C3A 1.15(3) 6_565 ?
O2A C3A 1.15(3) . ?
O3A F4A 1.75(3) 6_565 ?
O3A C3A 1.28(3) . ?
O3A F8A 1.69(4) 5_666 ?
C3A F4A 1.68(3) 6_565 ?
C3A C3A 0.96(5) 6_565 ?
C3A C4A 1.30(5) . ?
C4A F4A 1.368(18) 6_565 ?
C4A F5A 1.32(5) 6_565 ?
C4A F6A 1.21(7) 6_565 ?
C4A C3A 1.31(5) 6_565 ?
F7A F7A 0.69(5) 6_565 ?
F7A F8A 1.67(4) 2_657 ?
F7A F9A 1.14(3) 6_565 ?
F7A F9A 0.92(3) . ?
F7A C6A 1.64(5) 5_667 ?
F7A C6A 1.52(6) . ?
F7A C6A 1.15(6) 2_657 ?
F8A O3A 1.69(4) 5_666 ?
F8A F7A 1.67(4) 2_657 ?
F8A C6A 1.46(7) . ?
F9A F7A 1.14(3) 6_565 ?
F9A F9A 0.66(4) 6_565 ?
F9A C6A 1.70(7) 5_667 ?
F9A C6A 1.69(6) 6_565 ?
F9A C6A 1.25(7) . ?
F9A C6A 1.26(8) 2_657 ?
O4A C5A 1.188(9) . ?
C5A O4A 1.188(9) 2_657 ?
C5A C6A 1.63(4) . ?
C5A C6A 1.63(4) 2_657 ?
C6A F7A 1.64(5) 5_667 ?
C6A F7A 1.15(6) 2_657 ?
C6A F9A 1.26(8) 2_657 ?
C6A F9A 1.70(7) 5_667 ?
C6A F9A 1.69(6) 6_565 ?
C6A C6A 0.59(12) 2_657 ?
C6A C6A 1.98(7) 6_565 ?
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
F3A F1A F1A 107.0(10) 6_565 6_565 ?
F3A F1A C2A 59.5(10) 6_565 . ?
C2A F1A F1A 54.4(6) . 6_565 ?
F3A F2A F2A 107.9(9) 6_565 6_565 ?
F3A F2A C2A 57.9(8) 6_565 . ?
C2A F2A F2A 56.8(6) . 6_565 ?
F1A F3A F2A 144.6(16) 6_565 6_565 ?
F1A F3A C2A 74.5(12) 6_565 . ?
F2A F3A C2A 71.7(11) 6_565 . ?
C1 N1 H1 119.3 . . ?
C1 N1 C5 121.5(6) . . ?
C5 N1 H1 119.3 . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
C8 N3 H3 117.3 . . ?
C11 N3 H3 117.3 . . ?
C11 N3 C8 125.5(7) . . ?
N1 C1 C2 119.9(6) . . ?
N1 C1 C10 115.4(6) . . ?
C2 C1 C10 124.7(6) . . ?
O1A C1A O1A 127.5(10) 6_565 . ?
O1A C1A C2A 116.2(5) 6_565 . ?
O1A C1A C2A 116.2(5) . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 122.1(7) . . ?
C3 C2 H2 119.0 . . ?
F1A C2A F1A 71.1(13) . 6_565 ?
F1A C2A F2A 137.6(11) 6_565 . ?
F1A C2A F2A 95.8(8) . . ?
F1A C2A F2A 95.8(8) 6_565 6_565 ?
F1A C2A F2A 137.6(11) . 6_565 ?
F1A C2A C1A 109.9(10) . . ?
F1A C2A C1A 109.9(10) 6_565 . ?
F2A C2A F2A 66.5(13) 6_565 . ?
F2A C2A C1A 112.5(9) . . ?
F2A C2A C1A 112.5(9) 6_565 . ?
F3A C2A F1A 110.1(13) 6_565 6_565 ?
F3A C2A F1A 110.1(13) . . ?
F3A C2A F1A 46.0(8) 6_565 . ?
F3A C2A F1A 46.0(8) . 6_565 ?
F3A C2A F2A 110.0(14) . . ?
F3A C2A F2A 110.0(14) 6_565 6_565 ?
F3A C2A F2A 50.3(8) . 6_565 ?
F3A C2A F2A 50.3(8) 6_565 . ?
F3A C2A F3A 126.6(14) . 6_565 ?
F3A C2A C1A 116.6(7) 6_565 . ?
F3A C2A C1A 116.6(7) . . ?
N2 C3 C2 121.1(6) . . ?
N2 C3 C4 121.3(6) . . ?
C2 C3 C4 117.6(7) . . ?
C5 C4 C3 118.2(6) . . ?
C5 C4 C9 118.6(6) . . ?
C9 C4 C3 123.2(6) . . ?
N1 C5 C4 120.7(6) . . ?
N1 C5 C6 118.6(6) . . ?
C4 C5 C6 120.7(6) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(7) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.1(6) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 N3 122.5(6) . . ?
C9 C8 N3 117.4(6) . . ?
C9 C8 C7 120.0(6) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 C4 120.6(6) . . ?
C8 C9 H9 119.7 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 N3 124.4(5) . . ?
O1 C11 N3 124.4(5) . 2 ?
N3 C11 N3 111.2(10) 2 . ?
O1S Na1 O1S 87.0(2) 5_666 2_656 ?
O1S Na1 O1S 87.0(2) 6_565 . ?
O1S Na1 O1S 93.0(2) 2_656 . ?
O1S Na1 O1S 180.00(16) 6_565 2_656 ?
O1S Na1 O1S 93.0(2) 5_666 6_565 ?
O1S Na1 O1S 180.0 5_666 . ?
O2A Na1 O1S 90.0(2) . 2_656 ?
O2A Na1 O1S 90.0(2) . . ?
O2A Na1 O1S 90.0(2) 5_666 2_656 ?
O2A Na1 O1S 90.0(2) 5_666 5_666 ?
O2A Na1 O1S 90.0(2) 5_666 6_565 ?
O2A Na1 O1S 90.0(2) . 5_666 ?
O2A Na1 O1S 90.0(2) 5_666 . ?
O2A Na1 O1S 90.0(2) . 6_565 ?
O2A Na1 O2A 180.0 5_666 . ?
F5A F4A O3A 111.5(17) 6_565 6_565 ?
F5A F4A C3A 96.8(15) 6_565 6_565 ?
F6A F4A F5A 82.3(15) 6_565 6_565 ?
F6A F4A O3A 122.9(15) 6_565 6_565 ?
F6A F4A C3A 80.9(17) 6_565 6_565 ?
F6A F4A C4A 53(3) 6_565 . ?
C3A F4A O3A 43.7(13) 6_565 6_565 ?
C4A F4A F5A 56(2) . 6_565 ?
C4A F4A O3A 88(3) . 6_565 ?
C4A F4A C3A 49(2) . 6_565 ?
F5A F5A F4A 129.7(9) 6_565 6_565 ?
F5A F5A C4A 70.5(10) 6_565 . ?
C4A F5A F4A 59.6(12) . 6_565 ?
F6A F6A F4A 131.4(13) 6_565 6_565 ?
F6A F6A C4A 67.4(18) 6_565 . ?
C4A F6A F4A 64.8(19) . 6_565 ?
Na1 O1S H1SA 113.4 . . ?
Na1 O1S H1SB 112.9 . . ?
H1SA O1S H1SB 105.4 . . ?
C3A O2A Na1 147.8(18) 6_565 . ?
C3A O2A Na1 147.8(18) . . ?
C3A O2A C3A 49(3) 6_565 . ?
C3A O3A F4A 65.2(18) . 6_565 ?
C3A O3A F8A 96.6(19) . 5_666 ?
F8A O3A F4A 79.9(14) 5_666 6_565 ?
O2A C3A F4A 159(3) . 6_565 ?
O2A C3A O3A 114(3) . . ?
O2A C3A C4A 130(3) . . ?
O3A C3A F4A 71.1(18) . 6_565 ?
O3A C3A C4A 116(3) . . ?
C3A C3A F4A 121.3(11) 6_565 6_565 ?
C3A C3A O2A 65.4(13) 6_565 . ?
C3A C3A O3A 149(2) 6_565 . ?
C3A C3A C4A 68.5(15) 6_565 . ?
C4A C3A F4A 52.8(14) . 6_565 ?
F4A C4A F4A 161(5) . 6_565 ?
F5A C4A F4A 103(3) 6_565 6_565 ?
F5A C4A F4A 64.3(16) . 6_565 ?
F5A C4A F4A 103(3) . . ?
F5A C4A F4A 64.3(16) 6_565 . ?
F5A C4A F5A 39(2) . 6_565 ?
F6A C4A F4A 62(2) 6_565 . ?
F6A C4A F4A 62(2) . 6_565 ?
F6A C4A F4A 107(5) . . ?
F6A C4A F4A 107(5) 6_565 6_565 ?
F6A C4A F5A 107(4) . 6_565 ?
F6A C4A F5A 92(3) 6_565 6_565 ?
F6A C4A F5A 92(3) . . ?
F6A C4A F5A 107(4) 6_565 . ?
F6A C4A F6A 45(4) 6_565 . ?
F6A C4A C3A 103(4) 6_565 6_565 ?
F6A C4A C3A 121(5) . 6_565 ?
F6A C4A C3A 121(5) 6_565 . ?
F6A C4A C3A 103(4) . . ?
C3A C4A F4A 77.8(19) 6_565 . ?
C3A C4A F4A 121(3) . . ?
C3A C4A F4A 121(3) 6_565 6_565 ?
C3A C4A F4A 77.8(19) . 6_565 ?
C3A C4A F5A 125(4) 6_565 6_565 ?
C3A C4A F5A 146(7) . 6_565 ?
C3A C4A F5A 125(4) . . ?
C3A C4A F5A 146(7) 6_565 . ?
C3A C4A C3A 43(3) . 6_565 ?
F7A F7A F8A 117.8(13) 6_565 2_657 ?
F7A F7A F9A 89(2) 6_565 . ?
F7A F7A F9A 53.6(15) 6_565 6_565 ?
F7A F7A C6A 35.5(19) 6_565 5_667 ?
F7A F7A C6A 114.9(18) 6_565 . ?
F7A F7A C6A 124(3) 6_565 2_657 ?
F9A F7A F8A 146(3) 6_565 2_657 ?
F9A F7A F8A 134(3) . 2_657 ?
F9A F7A F9A 35(3) . 6_565 ?
F9A F7A C6A 55(4) . . ?
F9A F7A C6A 96(4) 6_565 2_657 ?
F9A F7A C6A 77(3) 6_565 . ?
F9A F7A C6A 50(3) 6_565 5_667 ?
F9A F7A C6A 78(4) . 5_667 ?
F9A F7A C6A 75(5) . 2_657 ?
C6A F7A F8A 79(4) . 2_657 ?
C6A F7A F8A 59(4) 2_657 2_657 ?
C6A F7A F8A 102(3) 5_667 2_657 ?
C6A F7A C6A 88(4) 2_657 5_667 ?
C6A F7A C6A 20(6) 2_657 . ?
C6A F7A C6A 81(3) . 5_667 ?
F7A F8A O3A 150(2) 2_657 5_666 ?
C6A F8A O3A 113(4) . 5_666 ?
C6A F8A F7A 42(3) . 2_657 ?
F7A F9A F7A 37(3) . 6_565 ?
F7A F9A C6A 88(5) . . ?
F7A F9A C6A 62(3) 6_565 6_565 ?
F7A F9A C6A 90(4) . 6_565 ?
F7A F9A C6A 42(2) 6_565 5_667 ?
F7A F9A C6A 70(4) . 5_667 ?
F7A F9A C6A 61(3) . 2_657 ?
F7A F9A C6A 86(4) 6_565 2_657 ?
F7A F9A C6A 107(5) 6_565 . ?
F9A F9A F7A 91(2) 6_565 . ?
F9A F9A F7A 53.6(16) 6_565 6_565 ?
F9A F9A C6A 121(3) 6_565 2_657 ?
F9A F9A C6A 39(3) 6_565 5_667 ?
F9A F9A C6A 122(3) 6_565 . ?
F9A F9A C6A 39(2) 6_565 6_565 ?
C6A F9A C6A 83(5) . 6_565 ?
C6A F9A C6A 87(3) 2_657 6_565 ?
C6A F9A C6A 27(5) . 2_657 ?
C6A F9A C6A 87(3) . 5_667 ?
C6A F9A C6A 82(5) 2_657 5_667 ?
C6A F9A C6A 20(4) 6_565 5_667 ?
O4A C5A O4A 148.7(16) 2_657 . ?
O4A C5A C6A 106(3) . . ?
O4A C5A C6A 106(3) 2_657 2_657 ?
O4A C5A C6A 105(3) . 2_657 ?
O4A C5A C6A 105(3) 2_657 . ?
C6A C5A C6A 21(4) 2_657 . ?
F7A C6A F7A 20.5(17) 2_657 5_667 ?
F7A C6A F7A 118(4) 2_657 . ?
F7A C6A F7A 99(3) . 5_667 ?
F7A C6A F8A 78(4) 2_657 . ?
F7A C6A F9A 42(3) 2_657 5_667 ?
F7A C6A F9A 44(3) 2_657 2_657 ?
F7A C6A F9A 41.1(17) . 6_565 ?
F7A C6A F9A 72.9(19) 5_667 6_565 ?
F7A C6A F9A 111(3) 2_657 . ?
F7A C6A F9A 81(3) . 5_667 ?
F7A C6A F9A 31.7(17) 5_667 5_667 ?
F7A C6A F9A 93(3) 2_657 6_565 ?
F7A C6A C5A 106(3) . . ?
F7A C6A C5A 130(5) 2_657 . ?
F7A C6A C6A 65.1(18) . 6_565 ?
F7A C6A C6A 56(3) 2_657 6_565 ?
F7A C6A C6A 35.5(19) 5_667 6_565 ?
F8A C6A F7A 127(6) . . ?
F8A C6A F7A 84(3) . 5_667 ?
F8A C6A F9A 116(3) . 5_667 ?
F8A C6A F9A 92(4) . 6_565 ?
F8A C6A C5A 95(3) . . ?
F8A C6A C6A 95.3(18) . 6_565 ?
F9A C6A F7A 90(4) 2_657 . ?
F9A C6A F7A 37(2) . . ?
F9A C6A F7A 92(3) . 5_667 ?
F9A C6A F7A 44(2) 2_657 5_667 ?
F9A C6A F8A 90(6) . . ?
F9A C6A F8A 123(4) 2_657 . ?
F9A C6A F9A 93(3) 2_657 6_565 ?
F9A C6A F9A 110(4) . 2_657 ?
F9A C6A F9A 75(3) 6_565 5_667 ?
F9A C6A F9A 93(3) . 5_667 ?
F9A C6A F9A 19.3(15) 2_657 5_667 ?
F9A C6A F9A 19.4(15) . 6_565 ?
F9A C6A C5A 118(5) 2_657 . ?
F9A C6A C5A 119(4) . . ?
F9A C6A C6A 39(2) 5_667 6_565 ?
F9A C6A C6A 58(3) . 6_565 ?
F9A C6A C6A 59(3) 2_657 6_565 ?
F9A C6A C6A 39(2) 6_565 6_565 ?
C5A C6A F7A 149(5) . 5_667 ?
C5A C6A F9A 138(4) . 6_565 ?
C5A C6A F9A 136(5) . 5_667 ?
C5A C6A C6A 170(2) . 6_565 ?
C6A C6A F7A 41(10) 2_657 . ?
C6A C6A F7A 110(10) 2_657 5_667 ?
C6A C6A F7A 119(10) 2_657 2_657 ?
C6A C6A F8A 162(10) 2_657 . ?
C6A C6A F9A 79(10) 2_657 5_667 ?
C6A C6A F9A 78(10) 2_657 . ?
C6A C6A F9A 81(9) 2_657 6_565 ?
C6A C6A F9A 75(10) 2_657 2_657 ?
C6A C6A C5A 80(2) 2_657 . ?
C6A C6A C6A 90.007(8) 2_657 6_565 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1A 0.88 1.90 2.763(8) 167.6 .
N2 H2A O3A 0.88 1.88 2.751(16) 169.3 4_556
N2 H2B O1S 0.88 1.99 2.822(8) 156.4 7_566
N3 H3 O4A 0.88 1.97 2.808(11) 157.6 7_566
O1S H1SA O4A 0.96 1.84 2.745(10) 157.0 .
O1S H1SB O1A 0.95 1.82 2.765(7) 167.8 .
_shelx_res_file
;
tor99_a.res created by SHELXL-2014/7
TITL Tor99 in C2/m
REM SHELXT solution in C2/m
REM R1 0.320, Rweak 0.031, Alpha 0.070, Orientation as input
REM Formula found by SHELXT: C70 N16 O10 Na
CELL 0.71073 14.0292 22.3313 9.5059 90 92.95 90
ZERR 4 0.0011 0.0016 0.001 0 0.002 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H F N Na O
UNIT 104 104 30 24 2 36
EQIV $1 0.5-X,1.5-Y,1-Z
EQIV $2 0.5-X,0.5+Y,1-Z
RIGU 0.002 0.002 F1A F2A F3A C2A
RIGU 0.002 0.002 F4A F5A F6A O2A > C4A
RIGU 0.002 0.002 F7A > C6A
L.S. 10
PLAN 20
SIZE 0.053 0.021 0.016
TEMP -173.15
HTAB N1 O1A
HTAB N2 O1S_$1
HTAB N2 O3A_$2
HTAB N3 O4A_$1
HTAB O1S O1A
HTAB O1S O4A
BOND $H
ACTA 50
fmap 2
REM
REM
REM
WGHT 0.140900 31.272501
FVAR 0.18073
F1A 3 0.040357 0.464047 0.626357 10.50000 0.05740 0.08257 =
0.10727 -0.01258 -0.00633 -0.00925
F2A 3 0.071323 0.466003 0.839640 10.50000 0.06177 0.08612 =
0.10096 0.01822 0.00578 -0.00118
F3A 3 0.051349 0.549421 0.729640 10.50000 0.05521 0.05585 =
0.13231 0.00094 0.01095 0.00325
O1 6 0.000000 0.656988 0.000000 10.50000 0.07124 0.04559 =
0.03495 0.00000 -0.01423 0.00000
O1A 6 0.232647 0.550018 0.682956 11.00000 0.05176 0.05196 =
0.05153 -0.00346 -0.00306 -0.00557
N1 4 0.171405 0.666557 0.640942 11.00000 0.03600 0.04471 =
0.03607 -0.00032 -0.00914 -0.00401
AFIX 43
H1 2 0.181915 0.628046 0.653780 11.00000 -1.20000
AFIX 0
N2 4 0.125612 0.847124 0.585799 11.00000 0.04498 0.05625 =
0.04051 -0.00972 -0.01383 0.00640
AFIX 93
H2A 2 0.136189 0.871438 0.657765 11.00000 -1.20000
H2B 2 0.105352 0.861526 0.503430 11.00000 -1.20000
AFIX 0
N3 4 0.035661 0.746017 0.111069 11.00000 0.03293 0.04719 =
0.03070 0.00297 -0.00464 0.00221
AFIX 43
H3 2 0.036862 0.785001 0.097757 11.00000 -1.20000
AFIX 0
C1 1 0.187894 0.704752 0.750005 11.00000 0.02527 0.05454 =
0.03064 -0.00001 -0.00008 -0.00221
C1A 1 0.194293 0.500000 0.692499 10.50000 0.04648 0.03928 =
0.03366 0.00000 -0.00981 0.00000
C2 1 0.172450 0.764667 0.731482 11.00000 0.02611 0.05492 =
0.03498 -0.00565 -0.00063 0.00245
AFIX 43
H2 2 0.183923 0.790887 0.809214 11.00000 -1.20000
AFIX 0
C2A 1 0.090371 0.500000 0.722520 10.50000 0.04375 0.05203 =
0.08478 0.00000 -0.00122 0.00000
C3 1 0.140228 0.788686 0.601499 11.00000 0.01999 0.05364 =
0.04487 -0.00178 -0.00237 0.00417
C4 1 0.122059 0.747465 0.485755 11.00000 0.02542 0.04416 =
0.03341 -0.00541 0.00034 0.00105
C5 1 0.138441 0.686681 0.509901 11.00000 0.02747 0.05384 =
0.03357 0.00037 -0.00363 -0.00456
C6 1 0.121735 0.644572 0.401599 11.00000 0.04160 0.04585 =
0.03884 -0.00582 -0.00504 -0.00640
AFIX 43
H6 2 0.133206 0.603259 0.419283 11.00000 -1.20000
AFIX 0
C7 1 0.088755 0.663166 0.269900 11.00000 0.04168 0.04716 =
0.03531 -0.00606 -0.00515 -0.00645
AFIX 43
H7 2 0.078416 0.634746 0.196329 11.00000 -1.20000
AFIX 0
C8 1 0.070294 0.724368 0.244063 11.00000 0.02477 0.05436 =
0.03407 -0.00063 -0.00096 0.00052
C9 1 0.086822 0.765823 0.350235 11.00000 0.02527 0.04770 =
0.03572 0.00088 -0.00214 0.00287
AFIX 43
H9 2 0.074460 0.807018 0.332264 11.00000 -1.20000
AFIX 0
C10 1 0.224071 0.676390 0.885626 11.00000 0.04250 0.05793 =
0.03028 0.00148 -0.00611 -0.00530
AFIX 137
H10A 2 0.193527 0.637291 0.896155 11.00000 -1.50000
H10B 2 0.208925 0.702245 0.964732 11.00000 -1.50000
H10C 2 0.293377 0.671119 0.884531 11.00000 -1.50000
AFIX 0
C11 1 0.000000 0.710945 0.000000 10.50000 0.02315 0.07674 =
0.02209 0.00000 0.00383 0.00000
NA1 5 0.500000 0.500000 0.500000 10.25000 0.05677 0.04003 =
0.06245 0.00000 0.00474 0.00000
F4A 3 0.244509 0.560442 0.139848 10.50000 0.23292 0.09916 =
0.13286 -0.00011 -0.07676 0.01419
F5A 3 0.236268 0.480365 0.024177 10.50000 0.25521 0.11436 =
0.14218 -0.01151 -0.10256 0.01610
F6A 3 0.186637 0.479197 0.197582 10.50000 0.24724 0.11051 =
0.15930 0.00161 -0.08898 -0.00191
O1S 6 0.422028 0.575636 0.642096 11.00000 0.05821 0.03796 =
0.06366 -0.00515 -0.00635 -0.00877
AFIX 7
H1SA 2 0.456538 0.584516 0.729046 11.00000 -1.50000
H1SB 2 0.359848 0.563836 0.667715 11.00000 -1.50000
AFIX 0
O2A 6 0.364249 0.500000 0.334497 10.50000 0.12066 0.12970 =
0.07396 0.00000 -0.01268 0.00000
O3A 6 0.363673 0.429492 0.198715 10.50000 0.28424 0.09995 =
0.05382 0.02624 -0.04714 0.03066
C3A 1 0.326077 0.478597 0.237220 10.50000 0.23306 0.10418 =
0.11077 -0.00513 -0.07928 0.01409
C4A 1 0.258422 0.500000 0.152237 10.25000 0.23963 0.09044 =
0.13524 0.00000 -0.09830 0.00000
F7A 3 0.441593 0.515482 0.910671 10.25000 0.13934 0.06667 =
0.11852 -0.02086 -0.03373 -0.00024
F8A 3 0.621507 0.550304 0.969551 10.25000 0.13536 0.09092 =
0.15164 -0.03309 -0.02658 0.00102
F9A 3 0.505076 0.514776 0.892499 10.25000 0.13988 0.05723 =
0.10222 -0.00563 -0.03564 0.00430
O4A 6 0.500042 0.630368 0.879615 11.00000 0.28990 0.07859 =
0.08867 0.00589 -0.04201 -0.01756
C5A 1 0.500000 0.616032 1.000000 10.50000 0.10755 0.05721 =
0.07350 0.00000 -0.03862 0.00000
C6A 1 0.521141 0.544242 1.002659 10.25000 0.13532 0.05911 =
0.09815 -0.00366 -0.03363 0.00106
HKLF 4
REM Tor99 in C2/m
REM R1 = 0.1119 for 1478 Fo > 4sig(Fo) and 0.1943 for all 2807 data
REM 298 parameters refined using 99 restraints
END
WGHT 0.1409 31.2556
REM Highest difference peak 0.891, deepest hole -0.599, 1-sigma level 0.100
Q1 1 0.1756 0.5000 0.3159 10.50000 0.05 0.80
Q2 1 0.1395 0.5000 0.1729 10.50000 0.05 0.73
Q3 1 0.0881 0.5000 0.8778 10.50000 0.05 0.63
Q4 1 0.2858 0.5826 0.1729 11.00000 0.05 0.56
Q5 1 0.0100 0.5000 0.6303 10.50000 0.05 0.56
Q6 1 0.3966 0.4292 0.1987 11.00000 0.05 0.53
Q7 1 0.2104 0.4522 0.1967 11.00000 0.05 0.48
Q8 1 0.2986 0.5000 -0.0070 10.50000 0.05 0.47
Q9 1 0.5540 0.5267 0.8682 11.00000 0.05 0.43
Q10 1 0.2613 0.5000 0.3492 10.50000 0.05 0.40
Q11 1 0.0713 0.4476 0.8095 11.00000 0.05 0.35
Q12 1 0.1961 0.5458 0.1110 11.00000 0.05 0.35
Q13 1 0.3821 0.5190 0.9583 11.00000 0.05 0.34
Q14 1 0.0441 0.4465 0.6667 11.00000 0.05 0.32
Q15 1 0.4260 0.5000 1.0083 10.50000 0.05 0.30
Q16 1 0.4630 0.5186 0.8748 11.00000 0.05 0.29
Q17 1 -0.0086 0.7735 0.1196 11.00000 0.05 0.26
Q18 1 0.1596 0.5000 -0.0427 10.50000 0.05 0.26
Q19 1 0.1783 0.5625 0.7051 11.00000 0.05 0.25
Q20 1 0.1501 0.7729 0.6578 11.00000 0.05 0.24
;
_shelx_res_checksum 1918
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'