# 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. 
# 
#######################################################################

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 λ/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       'ω and φ 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 > 2σ(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/[σ²(Fo²)+(0.0148P)²+0.3722P] where P=(Fo²+2Fc²)/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


_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) . . . . ?

_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 λ/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       'ω and φ 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 > 2σ(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/[σ²(Fo²)+(0.0139P)²+1.5049P] where P=(Fo²+2Fc²)/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 . . . .


_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) . . . . ?

_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 λ/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       'ω and φ 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 > 2σ(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/[σ²(Fo²)+(0.0156P)²+0.5893P] where P=(Fo²+2Fc²)/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 . . . . .


_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_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'
