# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
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data_tcd830
_database_code_depnum_ccdc_archive 'CCDC 1821079'
_audit_update_record
;
2018-01-31 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date 2017-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C12 H8 Cl4 N4 O4 Sb2, H2 O'
_chemical_formula_sum 'C12 H10 Cl4 N4 O5 Sb2'
_chemical_formula_weight 675.54
_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'
Sb Sb -0.5866 1.5461 '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 6.4349(2)
_cell_length_b 7.7809(2)
_cell_length_c 9.6588(3)
_cell_angle_alpha 81.4760(10)
_cell_angle_beta 81.5970(10)
_cell_angle_gamma 86.7140(10)
_cell_volume 472.82(2)
_cell_formula_units_Z 1
_cell_measurement_reflns_used 9908
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 36.51
_cell_measurement_theta_min 3.17
_shelx_estimated_absorpt_T_max 0.874
_shelx_estimated_absorpt_T_min 0.386
_exptl_absorpt_coefficient_mu 3.455
_exptl_absorpt_correction_T_max 0.7471
_exptl_absorpt_correction_T_min 0.5582
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0792 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.7472. The \l/2 correction factor is 0.00150.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour yellow
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 2.372
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 320
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.04
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0308
_diffrn_reflns_av_unetI/netI 0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 21969
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 36.540
_diffrn_reflns_theta_min 3.169
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'CMOS area detector'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type 'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device 'three-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Quest ECO'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_collimation '0.5 mm double-pinhole'
_diffrn_radiation_detector 'Bruker PHOTON 50'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'Siemens, KFF Mo 2K -90 C'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4339
_reflns_number_total 4643
_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 v8.37A (Bruker, 2015)'
_computing_data_collection 'APEX 3 (Bruker, 2016) '
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.736
_refine_diff_density_min -0.932
_refine_diff_density_rms 0.126
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.141
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 129
_refine_ls_number_reflns 4643
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0237
_refine_ls_R_factor_gt 0.0206
_refine_ls_restrained_S_all 1.141
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0148P)^2^+0.3722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0461
_refine_ls_wR_factor_ref 0.0470
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
2. Restrained distances
3. Uiso/Uaniso restraints and constraints
Uanis(C5B) = Uanis(C10B) = Uanis(C9B) = Uanis(C8B) = Uanis(C7B) = Uanis(N6B) =
Uanis(N6A) = Uanis(C5A) = Uanis(C7A) = Uanis(C8A) = Uanis(C9A) = Uanis(C10A)
4. Others
Sof(C5B)=Sof(C10B)=Sof(H10B)=Sof(C9B)=Sof(H9B)=Sof(C8B)=Sof(H8B)=Sof(C7B)=
Sof(H7B)=Sof(N6B)=1-FVAR(1)
Sof(N6A)=Sof(C5A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
Sof(C10A)=Sof(H10A)=FVAR(1)
Sof(Cl1B)=Sof(Cl2B)=1-FVAR(2)
Sof(Cl1A)=Sof(Cl2A)=FVAR(2)
Fixed Sof: O11(0.5) H11A(0.5) H11B(0.5)
5.a Aromatic/amide H refined with riding coordinates:
C10B(H10B), C9B(H9B), C8B(H8B), C7B(H7B), C7A(H7A), C8A(H8A), C9A(H9A),
C10A(H10A)
5.b Fitted hexagon refined as free rotating group:
C5B(C10B,C9B,C8B,C7B,N6B)
;
_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
Sb1 Sb 0.39976(2) 0.24401(2) 0.90838(2) 0.01157(3) Uani 1 1 d . . . . .
Cl1B Cl 0.5631(13) 0.5179(11) 0.7963(7) 0.0155(7) Uani 0.42(5) 1 d . . P A 2
Cl2B Cl 0.760(2) 0.106(2) 0.9980(14) 0.0202(12) Uani 0.42(5) 1 d . . P A 2
O1 O 0.54651(17) 0.11663(14) 0.75038(11) 0.01361(17) Uani 1 1 d . . . . .
O4 O 0.18937(17) 0.28254(14) 0.75709(11) 0.01431(17) Uani 1 1 d . . . . .
N2 N 0.43901(19) 0.11560(17) 0.63538(12) 0.01339(19) Uani 1 1 d . . . . .
C5B C 0.1306(8) 0.2130(8) 0.5345(5) 0.01223(11) Uani 0.294(5) 1 d . . P B 2
C10B C 0.1865(6) 0.1445(7) 0.4087(5) 0.01223(11) Uani 0.294(5) 1 d G . P B 2
H10B H 0.3187 0.0851 0.3910 0.015 Uiso 0.294(5) 1 calc R . P B 2
C9B C 0.0489(8) 0.1630(6) 0.3087(4) 0.01223(11) Uani 0.294(5) 1 d G . P B 2
H9B H 0.0871 0.1162 0.2227 0.015 Uiso 0.294(5) 1 calc R . P B 2
C8B C -0.1446(7) 0.2500(5) 0.3345(4) 0.01223(11) Uani 0.294(5) 1 d G . P B 2
H8B H -0.2386 0.2626 0.2661 0.015 Uiso 0.294(5) 1 calc R . P B 2
C7B C -0.2004(6) 0.3184(5) 0.4603(5) 0.01223(11) Uani 0.294(5) 1 d G . P B 2
H7B H -0.3326 0.3778 0.4779 0.015 Uiso 0.294(5) 1 calc R . P B 2
N6B N -0.0628(8) 0.2999(7) 0.5603(4) 0.01223(11) Uani 0.294(5) 1 d G . P B 2
C3 C 0.2614(2) 0.20288(17) 0.64863(14) 0.0116(2) Uani 1 1 d . . . . .
N6A N 0.2034(3) 0.1334(3) 0.4214(2) 0.01223(11) Uani 0.706(5) 1 d . . P B 1
C5A C 0.1298(4) 0.2145(4) 0.5350(3) 0.01223(11) Uani 0.706(5) 1 d . . P B 1
C7A C 0.0962(4) 0.1397(3) 0.3112(2) 0.01223(11) Uani 0.706(5) 1 d . . P B 1
H7A H 0.1514 0.0813 0.2334 0.015 Uiso 0.706(5) 1 calc R . P B 1
C8A C -0.0955(4) 0.2317(3) 0.3109(2) 0.01223(11) Uani 0.706(5) 1 d . . P B 1
H8A H -0.1708 0.2392 0.2326 0.015 Uiso 0.706(5) 1 calc R . P B 1
C9A C -0.1742(4) 0.3121(3) 0.4273(3) 0.01223(11) Uani 0.706(5) 1 d . . P B 1
H9A H -0.3055 0.3748 0.4296 0.015 Uiso 0.706(5) 1 calc R . P B 1
C10A C -0.0617(4) 0.3011(4) 0.5402(2) 0.01223(11) Uani 0.706(5) 1 d . . P B 1
H10A H -0.1173 0.3536 0.6211 0.015 Uiso 0.706(5) 1 calc R . P B 1
Cl1A Cl 0.590(2) 0.5089(10) 0.7893(8) 0.0247(8) Uani 0.58(5) 1 d . . P A 1
Cl2A Cl 0.7540(16) 0.1239(13) 0.9985(11) 0.0182(6) Uani 0.58(5) 1 d . . P A 1
O11 O 0.0410(6) 0.4789(5) -0.0076(5) 0.0298(7) Uani 0.5 1 d D . P C -1
H11A H -0.030(10) 0.476(7) -0.081(5) 0.045 Uiso 0.5 1 d DR . P D -1
H11B H 0.096(9) 0.582(4) -0.008(7) 0.045 Uiso 0.5 1 d DR . P E -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
Sb1 0.01483(4) 0.01120(4) 0.00905(4) -0.00276(2) -0.00126(3) -0.00131(3)
Cl1B 0.0190(13) 0.0117(8) 0.0159(11) -0.0018(5) -0.0019(6) -0.0016(6)
Cl2B 0.0141(13) 0.034(4) 0.0158(14) -0.0095(18) -0.0053(8) -0.0012(18)
O1 0.0145(4) 0.0161(4) 0.0115(4) -0.0051(3) -0.0039(3) 0.0016(3)
O4 0.0164(4) 0.0152(4) 0.0122(4) -0.0054(3) -0.0028(3) 0.0024(3)
N2 0.0132(5) 0.0170(5) 0.0110(4) -0.0046(4) -0.0027(4) -0.0006(4)
C5B 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C10B 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C9B 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C8B 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C7B 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
N6B 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C3 0.0127(5) 0.0118(5) 0.0107(5) -0.0023(4) -0.0021(4) -0.0017(4)
N6A 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C5A 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C7A 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C8A 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C9A 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
C10A 0.0117(3) 0.0131(2) 0.0125(3) -0.0034(2) -0.0024(2) 0.0004(2)
Cl1A 0.035(2) 0.0122(7) 0.0273(11) 0.0013(6) -0.0069(11) -0.0054(11)
Cl2A 0.0152(7) 0.0222(10) 0.0183(11) -0.0047(7) -0.0055(6) 0.0020(5)
O11 0.036(2) 0.0254(19) 0.0306(14) -0.0046(13) -0.0117(18) -0.0060(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
Sb1 Cl1B 2.462(8) . ?
Sb1 Cl2B 2.701(14) . ?
Sb1 O1 2.0306(10) . ?
Sb1 O4 2.1119(11) . ?
Sb1 Cl1A 2.499(7) . ?
Sb1 Cl2A 2.631(9) . ?
Cl2B Sb1 2.931(17) 2_657 ?
O1 N2 1.3928(16) . ?
O4 C3 1.3093(17) . ?
N2 C3 1.2951(18) . ?
C5B C10B 1.3900 . ?
C5B N6B 1.3900 . ?
C5B C3 1.472(3) . ?
C10B H10B 0.9500 . ?
C10B C9B 1.3900 . ?
C9B H9B 0.9500 . ?
C9B C8B 1.3900 . ?
C8B H8B 0.9500 . ?
C8B C7B 1.3900 . ?
C7B H7B 0.9500 . ?
C7B N6B 1.3900 . ?
C3 C5A 1.471(3) . ?
N6A C5A 1.359(3) . ?
N6A C7A 1.344(3) . ?
C5A C10A 1.368(3) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.390(3) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.384(3) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.385(3) . ?
C10A H10A 0.9500 . ?
O11 H11A 0.896(10) . ?
O11 H11B 0.896(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
Cl1B Sb1 Cl2B 93.2(4) . . ?
O1 Sb1 Cl1B 91.37(18) . . ?
O1 Sb1 Cl2B 74.5(3) . . ?
O1 Sb1 O4 76.58(4) . . ?
O1 Sb1 Cl1A 87.9(3) . . ?
O1 Sb1 Cl2A 76.3(2) . . ?
O4 Sb1 Cl1B 88.57(17) . . ?
O4 Sb1 Cl2B 151.1(3) . . ?
O4 Sb1 Cl1A 90.33(18) . . ?
O4 Sb1 Cl2A 152.8(2) . . ?
Cl1A Sb1 Cl2A 87.7(4) . . ?
Sb1 Cl2B Sb1 95.2(4) . 2_657 ?
N2 O1 Sb1 116.34(8) . . ?
C3 O4 Sb1 110.52(9) . . ?
C3 N2 O1 112.04(11) . . ?
C10B C5B N6B 120.0 . . ?
C10B C5B C3 125.5(3) . . ?
N6B C5B C3 114.5(3) . . ?
C5B C10B H10B 120.0 . . ?
C5B C10B C9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C9B C8B C7B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
N6B C7B C8B 120.0 . . ?
N6B C7B H7B 120.0 . . ?
C7B N6B C5B 120.0 . . ?
O4 C3 C5B 117.5(2) . . ?
O4 C3 C5A 117.05(16) . . ?
N2 C3 O4 124.48(12) . . ?
N2 C3 C5B 118.0(2) . . ?
N2 C3 C5A 118.48(16) . . ?
C7A N6A C5A 121.91(17) . . ?
N6A C5A C3 117.7(2) . . ?
N6A C5A C10A 119.45(18) . . ?
C10A C5A C3 122.9(2) . . ?
N6A C7A H7A 120.0 . . ?
N6A C7A C8A 120.06(18) . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A H8A 120.7 . . ?
C9A C8A C7A 118.62(18) . . ?
C9A C8A H8A 120.7 . . ?
C8A C9A H9A 120.0 . . ?
C8A C9A C10A 120.00(18) . . ?
C10A C9A H9A 120.0 . . ?
C5A C10A C9A 119.88(18) . . ?
C5A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
H11A O11 H11B 113.5(17) . . ?
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
C10B H10B O1 0.95 2.28 3.032(4) 135 2_656
C10B H10B N2 0.95 2.16 3.079(4) 163 2_656
C8B H8B Cl1B 0.95 2.70 3.446(9) 136 2_566
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
Sb1 O1 N2 C3 1.78(15) . . . . ?
Sb1 O4 C3 N2 -1.21(17) . . . . ?
Sb1 O4 C3 C5B 178.5(3) . . . . ?
Sb1 O4 C3 C5A 178.76(17) . . . . ?
O1 N2 C3 O4 -0.3(2) . . . . ?
O1 N2 C3 C5B 180.0(3) . . . . ?
O1 N2 C3 C5A 179.73(18) . . . . ?
O4 C3 C5A N6A 179.58(17) . . . . ?
O4 C3 C5A C10A -1.1(3) . . . . ?
N2 C3 C5A N6A -0.5(3) . . . . ?
N2 C3 C5A C10A 178.89(19) . . . . ?
C5B C10B C9B C8B 0.0 . . . . ?
C10B C5B N6B C7B 0.0 . . . . ?
C10B C5B C3 O4 176.4(2) . . . . ?
C10B C5B C3 N2 -3.8(5) . . . . ?
C10B C9B C8B C7B 0.0 . . . . ?
C9B C8B C7B N6B 0.0 . . . . ?
C8B C7B N6B C5B 0.0 . . . . ?
N6B C5B C10B C9B 0.0 . . . . ?
N6B C5B C3 O4 -3.4(4) . . . . ?
N6B C5B C3 N2 176.3(2) . . . . ?
C3 C5B C10B C9B -179.8(5) . . . . ?
C3 C5B N6B C7B 179.8(5) . . . . ?
C3 C5A C10A C9A 177.8(3) . . . . ?
N6A C5A C10A C9A -2.9(3) . . . . ?
N6A C7A C8A C9A -1.5(3) . . . . ?
C5A N6A C7A C8A 0.2(3) . . . . ?
C7A N6A C5A C3 -178.7(2) . . . . ?
C7A N6A C5A C10A 2.0(3) . . . . ?
C7A C8A C9A C10A 0.5(3) . . . . ?
C8A C9A C10A C5A 1.7(3) . . . . ?
_shelx_res_file
;
tcd830.res created by SHELXL-2014/7
TITL tcd830_a.res in P-1
REM Old TITL TCD830 in P1
REM SHELXT solution in P-1
REM R1 0.099, Rweak 0.016, Alpha 0.044, Orientation as input
REM Formula found by SHELXT: C14 N5 O2 Cl4 As2
CELL 0.71073 6.4349 7.7809 9.6588 81.476 81.597 86.714
ZERR 1 0.0002 0.0002 0.0003 0.001 0.001 0.001
LATT 1
SFAC C H Cl N O Sb
UNIT 12 10 4 4 5 2
EQIV $1 1-X,-Y,2-Z
EQIV $2 1-X,-Y,1-Z
EQIV $3 -X,1-Y,1-Z
DFIX 0.89 0.01 O11 H11b O11 H11a
DFIX 1.5 0.01 H11b H11a
EADP C5B C10B C9B C8B C7B N6B N6A C5A C7A C8A C9A C10A
L.S. 10
PLAN 20
SIZE 0.04 0.3 0.34
TEMP -173(2)
HTAB C10B O1_$2
HTAB C10B N2_$2
HTAB C8B Cl1B_$3
BIND Cl2B Sb1_$1
BOND $H
list 4
CONF
WPDB -2
fmap 2
acta
OMIT 0 1 0
REM
REM
REM
WGHT 0.014800 0.372200
FVAR 0.47332 0.70635 0.58333
SB1 6 0.399763 0.244014 0.908381 11.00000 0.01483 0.01120 =
0.00905 -0.00276 -0.00126 -0.00131
PART 2
CL1B 3 0.563139 0.517947 0.796312 -31.00000 0.01900 0.01172 =
0.01585 -0.00180 -0.00190 -0.00160
CL2B 3 0.759616 0.105700 0.998043 -31.00000 0.01413 0.03364 =
0.01576 -0.00949 -0.00530 -0.00121
PART 0
O1 5 0.546508 0.116630 0.750375 11.00000 0.01453 0.01609 =
0.01153 -0.00507 -0.00389 0.00161
O4 5 0.189372 0.282538 0.757089 11.00000 0.01643 0.01520 =
0.01221 -0.00535 -0.00277 0.00242
N2 4 0.439014 0.115599 0.635381 11.00000 0.01324 0.01702 =
0.01104 -0.00458 -0.00273 -0.00065
PART 2
AFIX 66
C5B 1 0.130637 0.212952 0.534504 -21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
C10B 1 0.186482 0.144508 0.408677 -21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 43
H10B 2 0.318690 0.085081 0.391038 -21.00000 -1.20000
AFIX 65
C9B 1 0.048888 0.163016 0.308658 -21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 43
H9B 2 0.087057 0.116238 0.222661 -21.00000 -1.20000
AFIX 65
C8B 1 -0.144552 0.249968 0.334466 -21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 43
H8B 2 -0.238591 0.262617 0.266107 -21.00000 -1.20000
AFIX 65
C7B 1 -0.200399 0.318413 0.460293 -21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 43
H7B 2 -0.332607 0.377840 0.477930 -21.00000 -1.20000
AFIX 65
N6B 4 -0.062807 0.299906 0.560312 -21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 0
PART 0
C3 1 0.261439 0.202881 0.648632 11.00000 0.01265 0.01182 =
0.01071 -0.00229 -0.00208 -0.00166
PART 1
N6A 4 0.203380 0.133370 0.421362 21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
C5A 1 0.129839 0.214486 0.534995 21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
C7A 1 0.096162 0.139709 0.311169 21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 43
H7A 2 0.151406 0.081268 0.233370 21.00000 -1.20000
AFIX 0
C8A 1 -0.095478 0.231689 0.310929 21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 43
H8A 2 -0.170848 0.239214 0.232561 21.00000 -1.20000
AFIX 0
C9A 1 -0.174230 0.312104 0.427264 21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 43
H9A 2 -0.305488 0.374824 0.429626 21.00000 -1.20000
AFIX 0
C10A 1 -0.061675 0.301119 0.540195 21.00000 0.01168 0.01315 =
0.01248 -0.00341 -0.00241 0.00035
AFIX 43
H10A 2 -0.117329 0.353639 0.621133 21.00000 -1.20000
AFIX 0
CL1A 3 0.590157 0.508860 0.789294 31.00000 0.03476 0.01216 =
0.02733 0.00125 -0.00691 -0.00538
CL2A 3 0.753997 0.123871 0.998452 31.00000 0.01523 0.02217 =
0.01830 -0.00473 -0.00546 0.00202
PART 0
PART -1
O11 5 0.041026 0.478938 -0.007636 10.50000 0.03623 0.02540 =
0.03064 -0.00464 -0.01166 -0.00599
H11A 2 -0.029691 0.476207 -0.080591 10.50000 -1.50000
H11B 2 0.096443 0.582045 -0.007722 10.50000 -1.50000
HKLF 4
REM tcd830_a.res in P-1
REM R1 = 0.0206 for 4339 Fo > 4sig(Fo) and 0.0237 for all 4643 data
REM 129 parameters refined using 3 restraints
END
WGHT 0.0148 0.3722
REM Highest difference peak 0.736, deepest hole -0.932, 1-sigma level 0.126
Q1 1 0.0012 0.2132 0.3075 11.00000 0.05 0.65
Q2 1 -0.1318 0.3146 0.4728 11.00000 0.05 0.61
Q3 1 0.3412 0.1474 0.6443 11.00000 0.05 0.61
Q4 1 -0.1439 0.2961 0.3762 11.00000 0.05 0.57
Q5 1 0.2168 0.2121 0.5947 11.00000 0.05 0.52
Q6 1 0.1782 0.1746 0.4790 11.00000 0.05 0.47
Q7 1 -0.1358 0.1961 0.3364 11.00000 0.05 0.47
Q8 1 0.3762 0.2036 0.1372 11.00000 0.05 0.44
Q9 1 0.0528 0.2421 0.5355 11.00000 0.05 0.44
Q10 1 0.4104 0.0691 0.8095 11.00000 0.05 0.44
Q11 1 0.4225 0.1571 0.9986 11.00000 0.05 0.43
Q12 1 0.2302 0.2561 0.7037 11.00000 0.05 0.42
Q13 1 0.1150 0.1522 0.3787 11.00000 0.05 0.42
Q14 1 0.5071 0.3468 1.0224 11.00000 0.05 0.40
Q15 1 0.0499 0.1059 0.3251 11.00000 0.05 0.40
Q16 1 0.3917 0.6339 0.9017 11.00000 0.05 0.40
Q17 1 0.4896 0.0457 0.5860 11.00000 0.05 0.39
Q18 1 -0.4335 0.3187 0.2607 11.00000 0.05 0.38
Q19 1 0.0996 0.5176 -0.2571 11.00000 0.05 0.37
Q20 1 0.2609 0.5427 -0.0959 11.00000 0.05 0.37
;
_shelx_res_checksum 96546
_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_tcd832
_database_code_depnum_ccdc_archive 'CCDC 1821080'
_audit_update_record
;
2018-01-31 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date 2017-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H12 Cl N2 O4 Sb'
_chemical_formula_sum 'C14 H12 Cl N2 O4 Sb'
_chemical_formula_weight 429.46
_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'
Sb Sb -0.5866 1.5461 '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 10.9598(4)
_cell_length_b 4.9157(2)
_cell_length_c 27.3577(11)
_cell_angle_alpha 90
_cell_angle_beta 96.0053(16)
_cell_angle_gamma 90
_cell_volume 1465.81(10)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9933
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 33.18
_cell_measurement_theta_min 2.99
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 2.084
_exptl_absorpt_correction_T_max 0.7465
_exptl_absorpt_correction_T_min 0.5659
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1191 before and 0.0415 after correction. The Ratio of minimum to maximum transmission is 0.7558. The \l/2 correction factor is 0.00150.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.946
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 840
_exptl_crystal_size_max 0.5
_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 0.0243
_diffrn_reflns_av_unetI/netI 0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 42
_diffrn_reflns_limit_l_min -38
_diffrn_reflns_number 50221
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 33.195
_diffrn_reflns_theta_min 2.995
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'Bruker D8 Quest ECO'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type 'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device 'three-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Quest ECO'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'standard sealed x-ray tube'
_diffrn_source_target Mo
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5355
_reflns_number_total 5612
_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 v8.37A (Bruker, 2015)'
_computing_data_collection 'APEX 3 (Bruker, 2016) '
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.656
_refine_diff_density_min -0.866
_refine_diff_density_rms 0.095
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.214
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 205
_refine_ls_number_reflns 5612
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0214
_refine_ls_R_factor_gt 0.0196
_refine_ls_restrained_S_all 1.215
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0139P)^2^+1.5049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0445
_refine_ls_wR_factor_ref 0.0450
_refine_special_details
'Donor H atoms located and refined with Uiso = 1.2x Ueq.'
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H,H) groups
2. Restrained distances
N12-H12 = N2-H2
1 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
C19(H19), C20(H20)
;
_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
Sb1 Sb 0.48954(2) -0.02551(2) 0.42271(2) 0.00854(3) Uani 1 1 d . . . . .
Cl1 Cl 0.70162(3) 0.14228(7) 0.44828(2) 0.01405(6) Uani 1 1 d . . . . .
O1 O 0.46850(9) 0.2935(2) 0.37479(4) 0.01283(18) Uani 1 1 d . . . . .
O4 O 0.58874(10) -0.1283(2) 0.34376(4) 0.01197(17) Uani 1 1 d . . . . .
O11 O 0.45164(9) 0.2484(2) 0.47690(4) 0.01109(17) Uani 1 1 d . . . . .
O14 O 0.28556(9) 0.0527(2) 0.41261(4) 0.01264(17) Uani 1 1 d . . . . .
N2 N 0.54921(11) 0.3180(2) 0.33968(4) 0.01120(19) Uani 1 1 d D . . . .
N12 N 0.33797(10) 0.3702(2) 0.46890(4) 0.01066(19) Uani 1 1 d D . . . .
C3 C 0.60370(12) 0.0999(3) 0.32400(5) 0.0095(2) Uani 1 1 d . . . . .
C5 C 0.67940(12) 0.1371(3) 0.28278(5) 0.0105(2) Uani 1 1 d . . . . .
C6 C 0.65138(13) 0.3409(3) 0.24755(5) 0.0133(2) Uani 1 1 d . . . . .
H6 H 0.5843 0.4600 0.2505 0.016 Uiso 1 1 calc R . . . .
C7 C 0.72153(15) 0.3695(3) 0.20829(5) 0.0175(3) Uani 1 1 d . . . . .
H7 H 0.7023 0.5075 0.1844 0.021 Uiso 1 1 calc R . . . .
C8 C 0.81963(16) 0.1956(3) 0.20423(6) 0.0196(3) Uani 1 1 d . . . . .
H8 H 0.8675 0.2147 0.1774 0.024 Uiso 1 1 calc R . . . .
C9 C 0.84840(15) -0.0071(3) 0.23919(6) 0.0194(3) Uani 1 1 d . . . . .
H9 H 0.9162 -0.1242 0.2364 0.023 Uiso 1 1 calc R . . . .
C10 C 0.77776(14) -0.0378(3) 0.27823(5) 0.0147(2) Uani 1 1 d . . . . .
H10 H 0.7965 -0.1777 0.3018 0.018 Uiso 1 1 calc R . . . .
C13 C 0.25531(12) 0.2625(3) 0.43600(5) 0.0107(2) Uani 1 1 d . . . . .
C15 C 0.13253(12) 0.3872(3) 0.42521(5) 0.0114(2) Uani 1 1 d . . . . .
C16 C 0.05687(14) 0.2877(3) 0.38519(6) 0.0181(3) Uani 1 1 d . . . . .
H16 H 0.0842 0.1424 0.3662 0.022 Uiso 1 1 calc R . . . .
C17 C -0.05869(15) 0.4006(4) 0.37300(6) 0.0218(3) Uani 1 1 d . . . . .
H17 H -0.1097 0.3332 0.3455 0.026 Uiso 1 1 calc R . . . .
H2 H 0.569(2) 0.507(2) 0.3325(9) 0.026 Uiso 1 1 d DR . . . .
H12 H 0.328(2) 0.520(4) 0.4920(7) 0.026 Uiso 1 1 d DR . . . .
C18 C -0.09974(13) 0.6106(3) 0.40077(6) 0.0167(3) Uani 1 1 d . . . . .
H18 H -0.1791 0.6860 0.3926 0.020 Uiso 1 1 calc R . . . .
C19 C -0.02455(15) 0.7102(4) 0.44053(6) 0.0210(3) Uani 1 1 d . . . . .
H19 H -0.0524 0.8551 0.4595 0.025 Uiso 1 1 calc R . . . .
C20 C 0.09141(14) 0.5999(4) 0.45297(6) 0.0197(3) Uani 1 1 d . . . . .
H20 H 0.1425 0.6693 0.4803 0.024 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
Sb1 0.01081(4) 0.00763(4) 0.00740(4) -0.00094(3) 0.00208(3) -0.00041(3)
Cl1 0.01067(12) 0.01768(14) 0.01394(13) -0.00453(11) 0.00194(10) -0.00113(11)
O1 0.0162(4) 0.0115(4) 0.0119(4) 0.0024(3) 0.0068(3) 0.0035(3)
O4 0.0180(5) 0.0080(4) 0.0104(4) 0.0008(3) 0.0035(3) -0.0001(3)
O11 0.0097(4) 0.0135(4) 0.0098(4) -0.0025(3) 0.0002(3) 0.0033(3)
O14 0.0122(4) 0.0130(4) 0.0130(4) -0.0038(3) 0.0024(3) -0.0008(3)
N2 0.0151(5) 0.0086(4) 0.0106(5) 0.0009(4) 0.0045(4) 0.0008(4)
N12 0.0100(4) 0.0116(5) 0.0102(5) -0.0018(4) 0.0007(4) 0.0023(4)
C3 0.0126(5) 0.0091(5) 0.0067(5) -0.0003(4) -0.0004(4) -0.0004(4)
C5 0.0126(5) 0.0105(5) 0.0083(5) -0.0019(4) 0.0012(4) -0.0018(4)
C6 0.0154(6) 0.0147(6) 0.0097(5) 0.0016(4) 0.0003(4) 0.0002(5)
C7 0.0232(7) 0.0186(6) 0.0109(6) 0.0034(5) 0.0034(5) -0.0017(5)
C8 0.0254(7) 0.0195(7) 0.0157(6) -0.0006(5) 0.0098(5) -0.0033(6)
C9 0.0211(7) 0.0174(7) 0.0213(7) -0.0008(5) 0.0100(5) 0.0022(5)
C10 0.0178(6) 0.0128(6) 0.0141(6) 0.0003(5) 0.0041(5) 0.0017(5)
C13 0.0121(5) 0.0121(5) 0.0082(5) -0.0001(4) 0.0025(4) -0.0010(4)
C15 0.0102(5) 0.0127(5) 0.0113(5) 0.0009(4) 0.0017(4) 0.0000(4)
C16 0.0158(6) 0.0207(7) 0.0170(6) -0.0062(5) -0.0020(5) 0.0012(5)
C17 0.0158(6) 0.0267(8) 0.0212(7) -0.0063(6) -0.0058(5) 0.0020(6)
C18 0.0122(6) 0.0204(7) 0.0174(6) 0.0028(5) 0.0003(5) 0.0009(5)
C19 0.0156(6) 0.0248(7) 0.0218(7) -0.0063(6) -0.0010(5) 0.0067(6)
C20 0.0142(6) 0.0245(7) 0.0193(7) -0.0087(6) -0.0036(5) 0.0055(5)
_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
Sb1 Cl1 2.4964(3) . ?
Sb1 O1 2.0416(10) . ?
Sb1 O4 2.5679(10) . ?
Sb1 O11 2.0766(10) . ?
Sb1 O14 2.2568(10) . ?
O1 N2 1.3774(15) . ?
O4 C3 1.2633(16) . ?
O11 N12 1.3789(15) . ?
O14 C13 1.2754(16) . ?
N2 C3 1.3201(17) . ?
N2 H2 0.978(9) . ?
N12 C13 1.3193(17) . ?
N12 H12 0.986(9) . ?
C3 C5 1.4797(18) . ?
C5 C6 1.4017(19) . ?
C5 C10 1.3946(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(2) . ?
C10 H10 0.9500 . ?
C13 C15 1.4800(19) . ?
C15 C16 1.391(2) . ?
C15 C20 1.395(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(2) . ?
C20 H20 0.9500 . ?
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
Cl1 Sb1 O4 80.62(2) . . ?
O1 Sb1 Cl1 88.02(3) . . ?
O1 Sb1 O4 68.92(4) . . ?
O1 Sb1 O11 86.72(4) . . ?
O1 Sb1 O14 75.32(4) . . ?
O11 Sb1 Cl1 80.54(3) . . ?
O11 Sb1 O4 149.54(4) . . ?
O11 Sb1 O14 72.98(4) . . ?
O14 Sb1 Cl1 149.25(3) . . ?
O14 Sb1 O4 115.57(4) . . ?
N2 O1 Sb1 118.50(8) . . ?
C3 O4 Sb1 105.69(8) . . ?
N12 O11 Sb1 114.40(7) . . ?
C13 O14 Sb1 112.49(9) . . ?
O1 N2 H2 113.2(15) . . ?
C3 N2 O1 120.06(11) . . ?
C3 N2 H2 126.1(15) . . ?
O11 N12 H12 112.6(15) . . ?
C13 N12 O11 118.59(11) . . ?
C13 N12 H12 128.5(15) . . ?
O4 C3 N2 119.91(12) . . ?
O4 C3 C5 122.96(12) . . ?
N2 C3 C5 117.12(12) . . ?
C6 C5 C3 120.83(12) . . ?
C10 C5 C3 119.48(12) . . ?
C10 C5 C6 119.67(12) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.25(13) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.66(14) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.48(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.99(14) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 119.95(14) . . ?
C9 C10 H10 120.0 . . ?
O14 C13 N12 118.08(12) . . ?
O14 C13 C15 120.89(12) . . ?
N12 C13 C15 120.99(12) . . ?
C16 C15 C13 117.77(13) . . ?
C16 C15 C20 119.48(13) . . ?
C20 C15 C13 122.74(13) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.08(14) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.38(14) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.62(14) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.55(15) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.87(14) . . ?
C19 C20 H20 120.1 . . ?
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
C7 H7 O14 0.95 2.68 3.4210(18) 135.2 2_655
N2 H2 O4 0.978(9) 1.829(13) 2.7568(15) 157(2) 1_565
N12 H12 Cl1 0.986(9) 2.373(10) 3.3573(12) 176(2) 3_666
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
Sb1 O1 N2 C3 26.83(16) . . . . ?
Sb1 O4 C3 N2 -12.89(14) . . . . ?
Sb1 O4 C3 C5 168.00(10) . . . . ?
Sb1 O11 N12 C13 15.48(15) . . . . ?
Sb1 O14 C13 N12 -12.48(15) . . . . ?
Sb1 O14 C13 C15 165.31(9) . . . . ?
O1 N2 C3 O4 -5.16(19) . . . . ?
O1 N2 C3 C5 174.00(11) . . . . ?
O4 C3 C5 C6 149.53(13) . . . . ?
O4 C3 C5 C10 -28.67(19) . . . . ?
O11 N12 C13 O14 -1.09(18) . . . . ?
O11 N12 C13 C15 -178.88(11) . . . . ?
O14 C13 C15 C16 -7.1(2) . . . . ?
O14 C13 C15 C20 173.67(14) . . . . ?
N2 C3 C5 C6 -29.60(18) . . . . ?
N2 C3 C5 C10 152.20(13) . . . . ?
N12 C13 C15 C16 170.58(14) . . . . ?
N12 C13 C15 C20 -8.6(2) . . . . ?
C3 C5 C6 C7 -178.43(13) . . . . ?
C3 C5 C10 C9 179.04(14) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C5 C10 C9 0.8(2) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C5 -1.0(2) . . . . ?
C10 C5 C6 C7 -0.2(2) . . . . ?
C13 C15 C16 C17 -179.01(15) . . . . ?
C13 C15 C20 C19 179.26(15) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C15 C20 C19 0.1(2) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C20 C15 C16 C17 0.2(2) . . . . ?
_shelx_res_file
;
tcd832.res created by SHELXL-2014/7
TITL TCD832 in P2(1)/c
CELL 0.71073 10.9598 4.9157 27.3577 90 96.0053 90
ZERR 4 0.0004 0.0002 0.0011 0 0.0016 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O Sb
UNIT 56 48 4 8 16 4
EQIV $1 1-X,-Y,1-Z
EQIV $2 +X,1+Y,+Z
EQIV $3 1-X,1-Y,1-Z
EQIV $4 1-X,0.5+Y,0.5-Z
DFIX 1 0.01 N12 H12 N2 H2
L.S. 4
PLAN 20
TEMP -173(2)
RTAB SbO1 Sb1 O11_$1
HTAB N2 O4_$2
HTAB N12 Cl1_$3
HTAB C7 O14_$4
BOND $H
list 4
CONF
WPDB -2
fmap 2
acta
OMIT -1 0 2
OMIT 1 0 2
REM
REM
REM
WGHT 0.013900 1.504900
FVAR 0.13026
SB1 6 0.489541 -0.025511 0.422709 11.00000 0.01081 0.00763 =
0.00740 -0.00094 0.00208 -0.00041
CL1 3 0.701622 0.142283 0.448282 11.00000 0.01067 0.01768 =
0.01394 -0.00453 0.00194 -0.00113
O1 5 0.468500 0.293508 0.374785 11.00000 0.01621 0.01149 =
0.01191 0.00244 0.00682 0.00353
O4 5 0.588738 -0.128279 0.343755 11.00000 0.01801 0.00797 =
0.01035 0.00082 0.00349 -0.00011
O11 5 0.451645 0.248413 0.476896 11.00000 0.00971 0.01354 =
0.00985 -0.00252 0.00017 0.00326
O14 5 0.285558 0.052727 0.412607 11.00000 0.01219 0.01301 =
0.01296 -0.00381 0.00237 -0.00077
N2 4 0.549214 0.317958 0.339676 11.00000 0.01506 0.00864 =
0.01057 0.00093 0.00447 0.00076
N12 4 0.337966 0.370179 0.468896 11.00000 0.01004 0.01164 =
0.01023 -0.00185 0.00073 0.00230
C3 1 0.603704 0.099927 0.324004 11.00000 0.01257 0.00906 =
0.00666 -0.00026 -0.00036 -0.00039
C5 1 0.679404 0.137146 0.282782 11.00000 0.01255 0.01055 =
0.00829 -0.00187 0.00123 -0.00180
C6 1 0.651384 0.340929 0.247555 11.00000 0.01543 0.01471 =
0.00966 0.00157 0.00026 0.00016
AFIX 43
H6 2 0.584258 0.459977 0.250488 11.00000 -1.20000
AFIX 0
C7 1 0.721528 0.369539 0.208295 11.00000 0.02322 0.01864 =
0.01095 0.00344 0.00339 -0.00172
AFIX 43
H7 2 0.702330 0.507484 0.184404 11.00000 -1.20000
AFIX 0
C8 1 0.819629 0.195555 0.204232 11.00000 0.02535 0.01947 =
0.01566 -0.00062 0.00981 -0.00325
AFIX 43
H8 2 0.867538 0.214665 0.177435 11.00000 -1.20000
AFIX 0
C9 1 0.848403 -0.007089 0.239185 11.00000 0.02109 0.01745 =
0.02132 -0.00078 0.01002 0.00224
AFIX 43
H9 2 0.916240 -0.124245 0.236351 11.00000 -1.20000
AFIX 0
C10 1 0.777759 -0.037761 0.278226 11.00000 0.01780 0.01279 =
0.01410 0.00033 0.00408 0.00171
AFIX 43
H10 2 0.796510 -0.177737 0.301759 11.00000 -1.20000
AFIX 0
C13 1 0.255309 0.262461 0.435997 11.00000 0.01207 0.01208 =
0.00825 -0.00013 0.00255 -0.00104
C15 1 0.132535 0.387177 0.425207 11.00000 0.01025 0.01273 =
0.01127 0.00091 0.00170 -0.00005
C16 1 0.056868 0.287659 0.385193 11.00000 0.01582 0.02073 =
0.01698 -0.00623 -0.00201 0.00119
AFIX 43
H16 2 0.084151 0.142404 0.366175 11.00000 -1.20000
AFIX 0
C17 1 -0.058688 0.400572 0.372997 11.00000 0.01575 0.02672 =
0.02120 -0.00628 -0.00577 0.00204
AFIX 43
H17 2 -0.109745 0.333186 0.345451 11.00000 -1.20000
AFIX 0
H2 2 0.568863 0.506865 0.332472 11.00000 -1.20000
H12 2 0.327734 0.520188 0.492032 11.00000 -1.20000
C18 1 -0.099736 0.610644 0.400774 11.00000 0.01223 0.02039 =
0.01736 0.00277 0.00033 0.00094
AFIX 43
H18 2 -0.179068 0.685951 0.392577 11.00000 -1.20000
AFIX 0
C19 1 -0.024550 0.710207 0.440529 11.00000 0.01565 0.02480 =
0.02179 -0.00632 -0.00102 0.00667
AFIX 43
H19 2 -0.052354 0.855135 0.459488 11.00000 -1.20000
AFIX 0
C20 1 0.091405 0.599894 0.452972 11.00000 0.01419 0.02446 =
0.01931 -0.00866 -0.00361 0.00554
AFIX 43
H20 2 0.142495 0.669305 0.480332 11.00000 -1.20000
AFIX 0
HKLF 4
REM TCD832 in P2(1)/c
REM R1 = 0.0196 for 5355 Fo > 4sig(Fo) and 0.0214 for all 5612 data
REM 205 parameters refined using 2 restraints
END
WGHT 0.0139 1.5049
REM Highest difference peak 0.656, deepest hole -0.866, 1-sigma level 0.095
Q1 1 0.4948 -0.1607 0.4238 11.00000 0.05 0.66
Q2 1 0.5293 0.4232 0.2298 11.00000 0.05 0.61
Q3 1 0.5765 0.2138 0.3318 11.00000 0.05 0.54
Q4 1 0.2933 0.3107 0.4557 11.00000 0.05 0.52
Q5 1 0.8185 -0.0136 0.2614 11.00000 0.05 0.48
Q6 1 0.7600 0.2642 0.2046 11.00000 0.05 0.48
Q7 1 0.1920 0.3531 0.4281 11.00000 0.05 0.45
Q8 1 0.0354 0.6693 0.4475 11.00000 0.05 0.43
Q9 1 0.8403 0.1056 0.2216 11.00000 0.05 0.42
Q10 1 -0.0824 0.5179 0.3848 11.00000 0.05 0.42
Q11 1 0.6384 0.1329 0.3029 11.00000 0.05 0.42
Q12 1 0.0003 0.3426 0.3807 11.00000 0.05 0.40
Q13 1 0.6887 0.3595 0.2275 11.00000 0.05 0.40
Q14 1 0.5558 0.4787 0.3894 11.00000 0.05 0.40
Q15 1 -0.0560 0.6680 0.4220 11.00000 0.05 0.39
Q16 1 0.2718 -0.1974 0.3978 11.00000 0.05 0.38
Q17 1 0.1017 0.3422 0.4017 11.00000 0.05 0.37
Q18 1 0.7018 0.2864 0.4478 11.00000 0.05 0.36
Q19 1 0.7401 0.0754 0.2820 11.00000 0.05 0.35
Q20 1 0.5771 0.4222 0.3374 11.00000 0.05 0.34
;
_shelx_res_checksum 72744
_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen holder'
_olex2_submission_original_sample_id DBG22
_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_tcd453
_database_code_depnum_ccdc_archive 'CCDC 1821081'
_audit_update_record
;
2018-01-31 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date 2016-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety
'C14 H15 N4 O4 Sb, 0.5(C2 H6 O), 2(H2 O), 2(Cl)'
_chemical_formula_sum 'C15 H22 Cl2 N4 O6.50 Sb'
_chemical_formula_weight 555.01
_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'
Sb Sb -0.5866 1.5461 '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 9.1379(3)
_cell_length_b 10.1593(4)
_cell_length_c 11.1638(4)
_cell_angle_alpha 82.915(2)
_cell_angle_beta 84.2630(10)
_cell_angle_gamma 86.2730(10)
_cell_volume 1021.87(6)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9748
_cell_measurement_temperature 100
_cell_measurement_theta_max 31.63
_cell_measurement_theta_min 2.77
_shelx_estimated_absorpt_T_max 0.839
_shelx_estimated_absorpt_T_min 0.603
_exptl_absorpt_coefficient_mu 1.654
_exptl_absorpt_correction_T_max 0.7462
_exptl_absorpt_correction_T_min 0.6549
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0548 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.8776.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.804
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 554
_exptl_crystal_recrystallization_method 'from saturated EtOH solution'
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.11
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0275
_diffrn_reflns_av_unetI/netI 0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 34395
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full 26.000
_diffrn_reflns_theta_max 31.670
_diffrn_reflns_theta_min 2.574
_diffrn_ambient_temperature 99.92
_diffrn_detector 'Bruker PHOTON 50 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type 'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Bruker D8 QUEST ECO'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'sealed X-ray tube'
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 6272
_reflns_number_total 6864
_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 'APEX 3 (Bruker, 2015) '
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'XP (Bruker, 2008-2014)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.476
_refine_diff_density_min -0.590
_refine_diff_density_rms 0.092
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.083
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 310
_refine_ls_number_reflns 6864
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0259
_refine_ls_R_factor_gt 0.0208
_refine_ls_restrained_S_all 1.083
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0156P)^2^+0.5893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0419
_refine_ls_wR_factor_ref 0.0434
_refine_special_details
'EtOH molecule disordered over inversion and modelled as a complete molecule half occupied.'
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4S) = Uanis(C5S)
3. Others
Fixed Sof: C4S(0.5) H4SA(0.5) H4SB(0.5) C5S(0.5) H5SA(0.5) H5SB(0.5)
H5SC(0.5) O3S(0.5) H3S(0.5)
4.a Secondary CH2 refined with riding coordinates:
C4S(H4SA,H4SB)
4.b Me refined with riding coordinates:
C5S(H5SA,H5SB,H5SC)
4.c Aromatic/amide H refined with riding coordinates:
C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17)
4.d Idealised tetrahedral OH refined as rotating group:
O3S(H3S)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.96296(14) 0.83660(13) 0.62708(12) 0.0092(2) Uani 1 1 d . . . . .
C3 C 1.08899(14) 0.90620(14) 0.62405(12) 0.0111(2) Uani 1 1 d . . . . .
H3 H 1.1819 0.8683 0.5958 0.013 Uiso 1 1 calc R . . . .
C4 C 1.07897(15) 1.03155(14) 0.66247(13) 0.0141(3) Uani 1 1 d . . . . .
H4 H 1.1653 1.0793 0.6607 0.017 Uiso 1 1 calc R . . . .
C5 C 0.94308(16) 1.08750(14) 0.70359(14) 0.0146(3) Uani 1 1 d . . . . .
H5 H 0.9364 1.1738 0.7288 0.018 Uiso 1 1 calc R . . . .
C6 C 0.81760(15) 1.01704(14) 0.70772(13) 0.0134(3) Uani 1 1 d . . . . .
H6 H 0.7253 1.0547 0.7375 0.016 Uiso 1 1 calc R . . . .
C7 C 0.82515(14) 0.89116(13) 0.66859(12) 0.0100(2) Uani 1 1 d . . . . .
C8 C 0.68996(14) 0.81859(13) 0.66861(12) 0.0098(2) Uani 1 1 d . . . . .
C13 C -0.04489(14) 0.61235(13) 0.88837(12) 0.0099(2) Uani 1 1 d . . . . .
C14 C -0.18451(15) 0.63759(15) 0.94788(13) 0.0130(3) Uani 1 1 d . . . . .
H14 H -0.2651 0.5895 0.9325 0.016 Uiso 1 1 calc R . . . .
C15 C -0.20666(16) 0.73136(16) 1.02855(14) 0.0175(3) Uani 1 1 d . . . . .
H15 H -0.3018 0.7458 1.0691 0.021 Uiso 1 1 calc R . . . .
C16 C -0.09125(17) 0.80496(17) 1.05113(14) 0.0186(3) Uani 1 1 d . . . . .
H16 H -0.1081 0.8718 1.1041 0.022 Uiso 1 1 calc R . . . .
C17 C 0.04851(15) 0.77974(15) 0.99555(13) 0.0141(3) Uani 1 1 d . . . . .
H17 H 0.1281 0.8284 1.0119 0.017 Uiso 1 1 calc R . . . .
C18 C 0.07336(14) 0.68279(14) 0.91530(12) 0.0101(2) Uani 1 1 d . . . . .
C19 C 0.22274(14) 0.65725(13) 0.85823(12) 0.0089(2) Uani 1 1 d . . . . .
N1 N 0.97912(13) 0.70520(12) 0.58604(11) 0.0097(2) Uani 1 1 d . . . . .
H1A H 0.910(2) 0.694(2) 0.5348(19) 0.023(5) Uiso 1 1 d . . . . .
H1B H 1.072(2) 0.691(2) 0.5520(18) 0.022(5) Uiso 1 1 d . . . . .
H1C H 0.967(2) 0.642(2) 0.647(2) 0.031(6) Uiso 1 1 d . . . . .
N10 N 0.56560(13) 0.88486(13) 0.64782(12) 0.0133(2) Uani 1 1 d . . . . .
H10 H 0.549(2) 0.967(2) 0.647(2) 0.030(6) Uiso 1 1 d . . . . .
N12 N -0.03009(13) 0.52357(12) 0.80056(11) 0.0107(2) Uani 1 1 d . . . . .
H12A H 0.055(2) 0.4841(19) 0.7902(18) 0.018(5) Uiso 1 1 d . . . . .
H12B H -0.103(2) 0.473(2) 0.8059(18) 0.020(5) Uiso 1 1 d . . . . .
N21 N 0.33687(12) 0.65604(12) 0.92047(11) 0.0105(2) Uani 1 1 d . . . . .
H21 H 0.336(2) 0.6607(19) 0.9955(18) 0.019(5) Uiso 1 1 d . . . . .
O9 O 0.69317(10) 0.69149(10) 0.68445(9) 0.01095(18) Uani 1 1 d . . . . .
O11 O 0.44155(10) 0.81538(10) 0.64605(10) 0.0144(2) Uani 1 1 d . . . . .
O20 O 0.24551(10) 0.63331(10) 0.74704(9) 0.01085(18) Uani 1 1 d . . . . .
O22 O 0.47574(10) 0.63280(11) 0.86449(9) 0.01303(19) Uani 1 1 d . . . . .
Sb1 Sb 0.47627(2) 0.61324(2) 0.68464(2) 0.00880(3) Uani 1 1 d . . . . .
C4S C 0.479(3) 0.933(3) 0.971(3) 0.030(2) Uani 0.5 1 d . . P A -1
H4SA H 0.5580 0.8931 0.9165 0.035 Uiso 0.5 1 calc R . P A -1
H4SB H 0.4505 0.8634 1.0376 0.035 Uiso 0.5 1 calc R . P A -1
C5S C 0.539(3) 1.046(3) 1.022(3) 0.030(2) Uani 0.5 1 d . . P A -1
H5SA H 0.6241 1.0125 1.0670 0.044 Uiso 0.5 1 calc R . P A -1
H5SB H 0.5706 1.1138 0.9565 0.044 Uiso 0.5 1 calc R . P A -1
H5SC H 0.4629 1.0841 1.0778 0.044 Uiso 0.5 1 calc R . P A -1
O3S O 0.3572(3) 0.9711(3) 0.9051(3) 0.0283(6) Uani 0.5 1 d . . P A -1
H3S H 0.3824 1.0256 0.8448 0.042 Uiso 0.5 1 calc GR . P A -1
O1S O 0.26416(12) 0.63720(11) 0.48785(10) 0.0154(2) Uani 1 1 d . . . . .
H1SA H 0.257(2) 0.551(2) 0.510(2) 0.034(6) Uiso 1 1 d . . . . .
H1SB H 0.280(3) 0.645(3) 0.417(2) 0.045(7) Uiso 1 1 d . . . . .
O2S O 0.47334(14) 1.14372(12) 0.68394(13) 0.0249(3) Uani 1 1 d . . . . .
H2SA H 0.407(3) 1.192(3) 0.647(2) 0.044(7) Uiso 1 1 d . . . . .
H2SB H 0.525(3) 1.197(3) 0.712(2) 0.052(8) Uiso 1 1 d . . . . .
Cl1 Cl 0.77349(4) 0.64726(3) 0.39126(3) 0.01647(7) Uani 1 1 d . . . . .
Cl2 Cl 0.65658(4) 0.35274(3) 0.79466(3) 0.01290(6) Uani 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
C2 0.0098(5) 0.0091(6) 0.0084(6) 0.0003(4) -0.0011(4) -0.0008(5)
C3 0.0083(5) 0.0124(6) 0.0124(6) 0.0009(5) -0.0021(5) -0.0014(5)
C4 0.0119(6) 0.0127(6) 0.0180(7) 0.0006(5) -0.0043(5) -0.0040(5)
C5 0.0153(6) 0.0110(6) 0.0188(7) -0.0029(5) -0.0050(5) -0.0016(5)
C6 0.0115(6) 0.0124(6) 0.0165(7) -0.0038(5) -0.0016(5) 0.0013(5)
C7 0.0087(5) 0.0101(6) 0.0115(6) -0.0007(5) -0.0020(5) -0.0017(5)
C8 0.0090(5) 0.0109(6) 0.0096(6) -0.0017(5) -0.0006(4) -0.0009(5)
C13 0.0103(5) 0.0107(6) 0.0081(6) 0.0015(5) -0.0022(4) -0.0001(5)
C14 0.0091(5) 0.0169(7) 0.0124(6) 0.0013(5) -0.0017(5) -0.0011(5)
C15 0.0110(6) 0.0254(8) 0.0152(7) -0.0029(6) -0.0005(5) 0.0049(6)
C16 0.0163(7) 0.0240(8) 0.0170(7) -0.0102(6) -0.0034(5) 0.0054(6)
C17 0.0117(6) 0.0165(7) 0.0153(7) -0.0055(5) -0.0035(5) 0.0013(5)
C18 0.0089(5) 0.0118(6) 0.0094(6) 0.0003(5) -0.0012(4) -0.0002(5)
C19 0.0091(5) 0.0066(5) 0.0110(6) -0.0004(4) -0.0013(4) -0.0014(4)
N1 0.0090(5) 0.0091(5) 0.0110(5) -0.0012(4) -0.0010(4) -0.0004(4)
N10 0.0088(5) 0.0099(6) 0.0219(6) -0.0025(5) -0.0027(4) -0.0026(4)
N12 0.0085(5) 0.0106(5) 0.0132(5) -0.0019(4) -0.0014(4) -0.0019(4)
N21 0.0074(5) 0.0158(6) 0.0086(5) -0.0024(4) -0.0002(4) -0.0007(4)
O9 0.0080(4) 0.0098(4) 0.0149(5) -0.0012(4) -0.0002(3) -0.0010(3)
O11 0.0064(4) 0.0111(5) 0.0267(6) -0.0024(4) -0.0042(4) -0.0022(4)
O20 0.0084(4) 0.0152(5) 0.0097(4) -0.0037(4) -0.0006(3) -0.0025(4)
O22 0.0064(4) 0.0217(5) 0.0117(5) -0.0058(4) -0.0002(3) 0.0000(4)
Sb1 0.00714(4) 0.00972(4) 0.00989(4) -0.00273(3) -0.00032(3) -0.00074(3)
C4S 0.039(6) 0.022(7) 0.029(3) 0.001(4) -0.010(3) -0.009(4)
C5S 0.039(6) 0.022(7) 0.029(3) 0.001(4) -0.010(3) -0.009(4)
O3S 0.0248(12) 0.0271(14) 0.0336(15) -0.0020(11) -0.0061(11) -0.0034(10)
O1S 0.0184(5) 0.0147(5) 0.0119(5) -0.0013(4) 0.0028(4) 0.0006(4)
O2S 0.0211(6) 0.0125(5) 0.0437(8) -0.0059(5) -0.0146(5) 0.0015(5)
Cl1 0.02097(16) 0.01118(15) 0.01872(17) -0.00208(12) -0.00857(13) -0.00106(13)
Cl2 0.01514(14) 0.01356(15) 0.01052(14) -0.00208(11) -0.00248(11) -0.00163(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
C2 C3 1.3855(18) . ?
C2 C7 1.4013(18) . ?
C2 N1 1.4579(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3846(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3969(19) . ?
C7 C8 1.4792(18) . ?
C8 N10 1.3089(18) . ?
C8 O9 1.2803(16) . ?
C13 C14 1.4017(19) . ?
C13 C18 1.4102(18) . ?
C13 N12 1.4031(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.4044(19) . ?
C18 C19 1.4688(18) . ?
C19 N21 1.3083(17) . ?
C19 O20 1.2883(16) . ?
N1 H1A 0.92(2) . ?
N1 H1B 0.91(2) . ?
N1 H1C 0.88(2) . ?
N10 H10 0.83(2) . ?
N10 O11 1.3768(14) . ?
N12 H12A 0.85(2) . ?
N12 H12B 0.86(2) . ?
N21 H21 0.84(2) . ?
N21 O22 1.3767(14) . ?
O9 Sb1 2.1826(9) . ?
O11 Sb1 2.0562(10) . ?
O20 Sb1 2.1584(9) . ?
O22 Sb1 2.0413(10) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
C4S C5S 1.504(4) . ?
C4S O3S 1.40(3) . ?
C5S H5SA 0.9800 . ?
C5S H5SB 0.9800 . ?
C5S H5SC 0.9800 . ?
O3S H3S 0.8400 . ?
O1S H1SA 0.88(2) . ?
O1S H1SB 0.79(3) . ?
O2S H2SA 0.86(3) . ?
O2S H2SB 0.85(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C7 120.82(12) . . ?
C3 C2 N1 117.71(12) . . ?
C7 C2 N1 121.48(11) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.73(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.27(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.83(13) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.79(13) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C8 120.87(12) . . ?
C6 C7 C2 118.56(12) . . ?
C6 C7 C8 120.56(12) . . ?
N10 C8 C7 119.64(12) . . ?
O9 C8 C7 121.16(12) . . ?
O9 C8 N10 119.15(12) . . ?
C14 C13 C18 118.24(13) . . ?
C14 C13 N12 118.85(12) . . ?
N12 C13 C18 122.83(12) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.97(13) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.77(13) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.35(14) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.51(13) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C19 120.44(12) . . ?
C17 C18 C13 120.09(12) . . ?
C17 C18 C19 119.46(12) . . ?
N21 C19 C18 120.41(12) . . ?
O20 C19 C18 121.51(12) . . ?
O20 C19 N21 118.07(12) . . ?
C2 N1 H1A 112.0(13) . . ?
C2 N1 H1B 109.9(13) . . ?
C2 N1 H1C 111.3(14) . . ?
H1A N1 H1B 112.1(18) . . ?
H1A N1 H1C 105.8(18) . . ?
H1B N1 H1C 105.6(19) . . ?
C8 N10 H10 126.5(15) . . ?
C8 N10 O11 118.76(12) . . ?
O11 N10 H10 113.9(15) . . ?
C13 N12 H12A 115.5(13) . . ?
C13 N12 H12B 112.9(13) . . ?
H12A N12 H12B 114.9(18) . . ?
C19 N21 H21 126.9(13) . . ?
C19 N21 O22 119.20(11) . . ?
O22 N21 H21 113.6(13) . . ?
C8 O9 Sb1 112.75(8) . . ?
N10 O11 Sb1 113.66(8) . . ?
C19 O20 Sb1 113.14(8) . . ?
N21 O22 Sb1 113.27(7) . . ?
O11 Sb1 O9 75.49(4) . . ?
O11 Sb1 O20 80.45(4) . . ?
O20 Sb1 O9 145.77(4) . . ?
O22 Sb1 O9 80.13(4) . . ?
O22 Sb1 O11 90.35(4) . . ?
O22 Sb1 O20 76.00(4) . . ?
H4SA C4S H4SB 107.7 . . ?
C5S C4S H4SA 108.9 . . ?
C5S C4S H4SB 108.9 . . ?
O3S C4S H4SA 108.9 . . ?
O3S C4S H4SB 108.9 . . ?
O3S C4S C5S 113.5(11) . . ?
C4S C5S H5SA 109.5 . . ?
C4S C5S H5SB 109.5 . . ?
C4S C5S H5SC 109.5 . . ?
H5SA C5S H5SB 109.5 . . ?
H5SA C5S H5SC 109.5 . . ?
H5SB C5S H5SC 109.5 . . ?
C4S O3S H3S 109.5 . . ?
H1SA O1S H1SB 105(2) . . ?
H2SA O2S H2SB 106(2) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O11 0.95 2.50 3.3176(16) 144 1_655
C14 H14 O22 0.95 2.55 3.3342(16) 140 1_455
N1 H1A Cl1 0.92(2) 2.24(2) 3.1436(12) 169.8(18) .
N1 H1B O1S 0.91(2) 1.90(2) 2.8010(16) 172.9(19) 1_655
N1 H1C N12 0.88(2) 1.97(2) 2.8350(17) 167(2) 1_655
N10 H10 O2S 0.83(2) 1.96(2) 2.7740(18) 165(2) .
N12 H12A O20 0.85(2) 2.359(19) 2.8004(15) 112.6(15) .
N12 H12A Cl1 0.85(2) 2.85(2) 3.5326(13) 138.7(16) 2_666
N12 H12B Cl2 0.86(2) 2.61(2) 3.4534(12) 169.8(18) 1_455
N21 H21 Cl2 0.84(2) 2.34(2) 3.1770(12) 173.2(18) 2_667
C4S H4SB Cl2 0.99 2.86 3.84(3) 171 2_667
C5S H5SB Cl2 0.98 2.94 3.91(3) 169 1_565
O3S H3S O2S 0.84 2.16 2.991(3) 171 .
O1S H1SA Cl1 0.88(2) 2.20(2) 3.0603(12) 166(2) 2_666
O1S H1SB Cl2 0.79(3) 2.37(3) 3.1551(12) 174(3) 2_666
O2S H2SA Cl1 0.86(3) 2.28(3) 3.1012(13) 161(2) 2_676
O2S H2SB Cl2 0.85(3) 2.38(3) 3.2193(13) 177(3) 1_565
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
C2 C3 C4 C5 -0.2(2) . . . . ?
C2 C7 C8 N10 -146.00(14) . . . . ?
C2 C7 C8 O9 31.55(19) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?
C3 C2 C7 C8 178.25(12) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C2 1.2(2) . . . . ?
C5 C6 C7 C8 -177.54(13) . . . . ?
C6 C7 C8 N10 32.7(2) . . . . ?
C6 C7 C8 O9 -149.79(14) . . . . ?
C7 C2 C3 C4 0.0(2) . . . . ?
C7 C8 N10 O11 178.84(12) . . . . ?
C7 C8 O9 Sb1 178.48(10) . . . . ?
C8 N10 O11 Sb1 2.36(16) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C13 C18 C19 N21 -141.18(13) . . . . ?
C13 C18 C19 O20 37.64(19) . . . . ?
C14 C13 C18 C17 -2.9(2) . . . . ?
C14 C13 C18 C19 178.16(12) . . . . ?
C14 C15 C16 C17 -2.6(2) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C16 C17 C18 C13 1.5(2) . . . . ?
C16 C17 C18 C19 -179.55(14) . . . . ?
C17 C18 C19 N21 39.90(19) . . . . ?
C17 C18 C19 O20 -141.28(14) . . . . ?
C18 C13 C14 C15 1.6(2) . . . . ?
C18 C19 N21 O22 -179.53(12) . . . . ?
C18 C19 O20 Sb1 175.98(10) . . . . ?
C19 N21 O22 Sb1 3.05(15) . . . . ?
N1 C2 C3 C4 -179.87(12) . . . . ?
N1 C2 C7 C6 179.39(12) . . . . ?
N1 C2 C7 C8 -1.9(2) . . . . ?
N10 C8 O9 Sb1 -3.96(16) . . . . ?
N12 C13 C14 C15 -175.26(13) . . . . ?
N12 C13 C18 C17 173.81(13) . . . . ?
N12 C13 C18 C19 -5.1(2) . . . . ?
N21 C19 O20 Sb1 -5.17(15) . . . . ?
O9 C8 N10 O11 1.2(2) . . . . ?
O20 C19 N21 O22 1.61(19) . . . . ?
_shelx_res_file
;
tcd453.res created by SHELXL-2014/7
TITL TCD453_a.res in P-1
CELL 0.71073 9.1379 10.1593 11.1638 82.915 84.263 86.273
ZERR 2 0.0003 0.0004 0.0004 0.002 0.001 0.001
LATT 1
SFAC C H Cl N O Sb
UNIT 30 44 4 8 13 2
EQIV $1 1+X,+Y,+Z
EQIV $2 1-X,1-Y,1-Z
EQIV $3 -1+X,+Y,+Z
EQIV $4 1-X,1-Y,2-Z
EQIV $5 1-X,2-Y,1-Z
EQIV $6 +X,1+Y,+Z
EADP C4S C5S
L.S. 10
PLAN 20
SIZE 0.11 0.17 0.34
TEMP -173.23
HTAB N1 Cl1
HTAB N1 O1S_$1
HTAB N1 N12_$1
HTAB C3 O11_$1
HTAB N10 O2S
HTAB N12 O20
HTAB N12 Cl1_$2
HTAB N12 Cl2_$3
HTAB C14 O22_$3
HTAB N21 Cl2_$4
HTAB O1S Cl1_$2
HTAB O1S Cl2_$2
HTAB O2S Cl1_$5
HTAB O2S Cl2_$6
HTAB O3S O2S
HTAB C4S Cl2_$4
HTAB C5S Cl2_$6
BOND $H
MORE -1
CONF
HTAB
WPDB -3
fmap 2
acta 52
OMIT 0 -1 1
REM
REM
REM
WGHT 0.015600 0.589300
FVAR 0.18454
C2 1 0.962957 0.836595 0.627081 11.00000 0.00984 0.00906 =
0.00842 0.00034 -0.00114 -0.00081
C3 1 1.088990 0.906199 0.624051 11.00000 0.00831 0.01244 =
0.01244 0.00088 -0.00208 -0.00141
AFIX 43
H3 2 1.181881 0.868268 0.595787 11.00000 -1.20000
AFIX 0
C4 1 1.078974 1.031548 0.662474 11.00000 0.01189 0.01273 =
0.01799 0.00058 -0.00434 -0.00403
AFIX 43
H4 2 1.165292 1.079336 0.660687 11.00000 -1.20000
AFIX 0
C5 1 0.943077 1.087502 0.703590 11.00000 0.01530 0.01095 =
0.01878 -0.00295 -0.00495 -0.00160
AFIX 43
H5 2 0.936362 1.173838 0.728770 11.00000 -1.20000
AFIX 0
C6 1 0.817602 1.017036 0.707723 11.00000 0.01152 0.01242 =
0.01647 -0.00383 -0.00157 0.00125
AFIX 43
H6 2 0.725280 1.054746 0.737528 11.00000 -1.20000
AFIX 0
C7 1 0.825148 0.891157 0.668591 11.00000 0.00872 0.01010 =
0.01151 -0.00073 -0.00201 -0.00166
C8 1 0.689958 0.818592 0.668607 11.00000 0.00898 0.01092 =
0.00961 -0.00174 -0.00057 -0.00087
C13 1 -0.044892 0.612355 0.888368 11.00000 0.01034 0.01074 =
0.00809 0.00151 -0.00221 -0.00014
C14 1 -0.184506 0.637586 0.947885 11.00000 0.00911 0.01689 =
0.01236 0.00130 -0.00172 -0.00112
AFIX 43
H14 2 -0.265080 0.589517 0.932542 11.00000 -1.20000
AFIX 0
C15 1 -0.206657 0.731363 1.028555 11.00000 0.01100 0.02541 =
0.01520 -0.00288 -0.00048 0.00491
AFIX 43
H15 2 -0.301766 0.745756 1.069071 11.00000 -1.20000
AFIX 0
C16 1 -0.091254 0.804956 1.051126 11.00000 0.01634 0.02401 =
0.01704 -0.01016 -0.00339 0.00544
AFIX 43
H16 2 -0.108131 0.871824 1.104115 11.00000 -1.20000
AFIX 0
C17 1 0.048505 0.779739 0.995550 11.00000 0.01175 0.01651 =
0.01530 -0.00555 -0.00353 0.00134
AFIX 43
H17 2 0.128131 0.828407 1.011860 11.00000 -1.20000
AFIX 0
C18 1 0.073362 0.682792 0.915297 11.00000 0.00890 0.01178 =
0.00937 0.00032 -0.00121 -0.00017
C19 1 0.222742 0.657248 0.858234 11.00000 0.00906 0.00657 =
0.01097 -0.00039 -0.00135 -0.00137
N1 4 0.979120 0.705200 0.586042 11.00000 0.00898 0.00910 =
0.01096 -0.00117 -0.00101 -0.00039
H1A 2 0.909803 0.693688 0.534836 11.00000 0.02279
H1B 2 1.072143 0.690517 0.551957 11.00000 0.02228
H1C 2 0.966907 0.642458 0.647076 11.00000 0.03057
N10 4 0.565599 0.884862 0.647824 11.00000 0.00882 0.00985 =
0.02187 -0.00254 -0.00267 -0.00260
H10 2 0.548711 0.966507 0.647072 11.00000 0.02973
N12 4 -0.030087 0.523566 0.800560 11.00000 0.00855 0.01065 =
0.01321 -0.00187 -0.00137 -0.00193
H12A 2 0.054669 0.484090 0.790151 11.00000 0.01827
H12B 2 -0.102611 0.473338 0.805910 11.00000 0.02004
N21 4 0.336873 0.656038 0.920471 11.00000 0.00738 0.01579 =
0.00857 -0.00242 -0.00018 -0.00073
H21 2 0.335653 0.660697 0.995515 11.00000 0.01863
O9 5 0.693170 0.691491 0.684451 11.00000 0.00796 0.00979 =
0.01492 -0.00116 -0.00024 -0.00103
O11 5 0.441546 0.815382 0.646053 11.00000 0.00638 0.01109 =
0.02669 -0.00243 -0.00416 -0.00222
O20 5 0.245511 0.633311 0.747038 11.00000 0.00844 0.01519 =
0.00968 -0.00368 -0.00057 -0.00249
O22 5 0.475736 0.632800 0.864486 11.00000 0.00638 0.02171 =
0.01175 -0.00579 -0.00021 0.00002
SB1 6 0.476274 0.613243 0.684642 11.00000 0.00714 0.00972 =
0.00989 -0.00273 -0.00032 -0.00074
PART -1
C4S 1 0.479219 0.932729 0.970590 10.50000 0.03911 0.02201 =
0.02883 0.00149 -0.01022 -0.00917
AFIX 23
H4SA 2 0.557997 0.893065 0.916541 10.50000 -1.20000
H4SB 2 0.450450 0.863407 1.037642 10.50000 -1.20000
AFIX 0
C5S 1 0.539450 1.045600 1.022488 10.50000 0.03911 0.02201 =
0.02883 0.00149 -0.01022 -0.00917
AFIX 33
H5SA 2 0.624125 1.012457 1.066973 10.50000 -1.50000
H5SB 2 0.570550 1.113776 0.956547 10.50000 -1.50000
H5SC 2 0.462913 1.084093 1.077751 10.50000 -1.50000
AFIX 0
O3S 5 0.357152 0.971117 0.905066 10.50000 0.02479 0.02710 =
0.03362 -0.00205 -0.00615 -0.00343
AFIX 147
H3S 2 0.382354 1.025563 0.844787 10.50000 -1.50000
AFIX 0
PART 0
O1S 5 0.264162 0.637198 0.487847 11.00000 0.01842 0.01473 =
0.01187 -0.00126 0.00275 0.00064
H1SA 2 0.256676 0.551300 0.509768 11.00000 0.03431
H1SB 2 0.279552 0.644834 0.416563 11.00000 0.04465
O2S 5 0.473335 1.143722 0.683944 11.00000 0.02114 0.01246 =
0.04375 -0.00590 -0.01465 0.00146
H2SA 2 0.407299 1.192312 0.647225 11.00000 0.04442
H2SB 2 0.524634 1.196587 0.712438 11.00000 0.05240
CL1 3 0.773490 0.647258 0.391259 11.00000 0.02097 0.01118 =
0.01872 -0.00208 -0.00857 -0.00106
CL2 3 0.656582 0.352736 0.794656 11.00000 0.01514 0.01356 =
0.01052 -0.00208 -0.00248 -0.00163
HKLF 4
REM TCD453_a.res in P-1
REM R1 = 0.0208 for 6272 Fo > 4sig(Fo) and 0.0259 for all 6864 data
REM 310 parameters refined using 0 restraints
END
WGHT 0.0156 0.5893
REM Instructions for potential hydrogen bonds
HTAB C3 O11_$1
HTAB C14 O22_$3
HTAB N1 Cl1
HTAB N1 O1S_$1
HTAB N1 N12_$1
HTAB N10 O2S
HTAB N12 O20
HTAB N12 Cl1_$2
HTAB N12 Cl2_$3
HTAB N21 Cl2_$4
HTAB C4S Cl2_$4
HTAB C5S Cl2_$6
HTAB O3S O2S
HTAB O1S Cl1_$2
HTAB O1S Cl2_$2
HTAB O2S Cl1_$5
HTAB O2S Cl2_$6
REM Highest difference peak 0.476, deepest hole -0.590, 1-sigma level 0.092
Q1 1 0.8981 0.8598 0.6689 11.00000 0.05 0.48
Q2 1 -0.1156 0.6437 0.9013 11.00000 0.05 0.47
Q3 1 1.0291 0.8691 0.6392 11.00000 0.05 0.46
Q4 1 -0.1866 0.6967 0.9774 11.00000 0.05 0.46
Q5 1 0.0183 0.6440 0.9153 11.00000 0.05 0.45
Q6 1 -0.0263 0.7771 1.0282 11.00000 0.05 0.44
Q7 1 -0.1540 0.7769 1.0225 11.00000 0.05 0.44
Q8 1 0.8797 1.0529 0.6844 11.00000 0.05 0.43
Q9 1 0.7707 0.8409 0.6665 11.00000 0.05 0.43
Q10 1 0.1419 0.6534 0.8992 11.00000 0.05 0.40
Q11 1 1.0089 1.0536 0.6786 11.00000 0.05 0.40
Q12 1 0.0063 0.6577 0.8885 11.00000 0.05 0.39
Q13 1 0.8790 0.8730 0.6271 11.00000 0.05 0.39
Q14 1 -0.0381 0.8056 1.0028 11.00000 0.05 0.38
Q15 1 0.0453 0.7327 0.9520 11.00000 0.05 0.38
Q16 1 0.7076 0.6359 0.4470 11.00000 0.05 0.37
Q17 1 0.8232 0.9451 0.6966 11.00000 0.05 0.35
Q18 1 0.4186 0.7883 0.7241 11.00000 0.05 0.35
Q19 1 0.6347 0.8649 0.6230 11.00000 0.05 0.34
Q20 1 -0.0307 0.5610 0.8570 11.00000 0.05 0.34
;
_shelx_res_checksum 94514
_shelx_SHELXL_version_number 2014/7
_olex2_exptl_crystal_mounting_method 'Mitegen holder in oil'
_olex2_submission_original_sample_id DGSb-1
_olex2_submission_special_instructions 'No special instructions were received'