# 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_Sd-23-DHTH
_database_code_depnum_ccdc_archive 'CCDC 1586508'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;
_audit_creation_date             2017-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_formula_moiety         'C22 H18 N4 O6'
_chemical_formula_sum            'C22 H18 N4 O6'
_chemical_formula_weight         434.40
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.8206(3)
_cell_length_b                   12.1575(5)
_cell_length_c                   12.4766(5)
_cell_angle_alpha                113.072(2)
_cell_angle_beta                 98.877(2)
_cell_angle_gamma                92.179(2)
_cell_volume                     934.89(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2543
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.92
_cell_measurement_temperature    100
_exptl_absorpt_coefficient_mu    0.964
_exptl_crystal_density_diffrn    1.5431
_exptl_crystal_F_000             452
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38'
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12993
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         3.92
_diffrn_ambient_temperature      100.0
_diffrn_measurement_device_type  Bruker
_diffrn_measured_fraction_theta_full 0.9500
_diffrn_measured_fraction_theta_max 0.9500
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2543
_reflns_number_total             3417
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3539
_refine_diff_density_min         -0.3290
_refine_diff_density_rms         0.0988
_refine_ls_d_res_high            0.8302
_refine_ls_d_res_low             11.2825
_refine_ls_goodness_of_fit_ref   1.0591
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.0591
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0820P)²+0.2813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1385
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3a), C2(H2a), C3(H3b), C4(H4a), C5(H5), C7(H7), C13(H13),
 C14(H14), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O6(H6)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O 0.03554(17) 1.07649(12) 0.28303(12) 0.0209(3) Uani 1.000000 .
H1 H 0.0601(5) 1.0266(14) 0.3133(18) 0.0314(5) Uiso 1.000000 GR
O2 O 0.32620(18) 0.90730(12) 0.43268(11) 0.0201(3) Uani 1.000000 .
O3 O 0.61674(17) 0.83522(12) 0.53315(11) 0.0189(3) Uani 1.000000 .
H3 H 0.5616(2) 0.8806(13) 0.5043(18) 0.0283(5) Uiso 1.000000 GR
O4 O 0.74780(17) 0.70323(12) 0.64638(12) 0.0193(3) Uani 1.000000 .
H4 H 0.7981(6) 0.7698(9) 0.6519(18) 0.0290(5) Uiso 1.000000 GR
O5 O 0.35024(19) 0.45527(13) 0.68704(12) 0.0237(3) Uani 1.000000 .
O6 O 0.65721(18) 0.30631(13) 0.86245(12) 0.0243(3) Uani 1.000000 .
H6 H 0.6326(2) 0.3513(16) 0.8265(18) 0.0365(5) Uiso 1.000000 GR
N1 N -0.0508(2) 0.90760(14) 0.35156(13) 0.0166(4) Uani 1.000000 .
N2 N 0.0070(2) 0.83021(14) 0.40388(13) 0.0164(3) Uani 1.000000 .
H2 H -0.0804(2) 0.77975(14) 0.41128(13) 0.0197(4) Uiso 1.000000 R
N3 N 0.6751(2) 0.52765(14) 0.71512(13) 0.0167(3) Uani 1.000000 .
H3a H 0.7619(2) 0.57649(14) 0.70501(13) 0.0200(4) Uiso 1.000000 R
N4 N 0.7368(2) 0.45472(14) 0.77104(13) 0.0171(3) Uani 1.000000 .
C1 C -0.1637(3) 1.06315(17) 0.23879(15) 0.0159(4) Uani 1.000000 .
C2 C -0.2301(3) 1.13573(17) 0.18155(15) 0.0187(4) Uani 1.000000 .
H2a H -0.1372(3) 1.18999(17) 0.17208(15) 0.0224(5) Uiso 1.000000 R
C3 C -0.4318(3) 1.12931(17) 0.13803(16) 0.0194(4) Uani 1.000000 .
H3b H -0.4764(3) 1.17872(17) 0.09815(16) 0.0232(5) Uiso 1.000000 R
C4 C -0.5691(3) 1.05117(17) 0.15233(16) 0.0192(4) Uani 1.000000 .
H4a H -0.7074(3) 1.04812(17) 0.12358(16) 0.0231(5) Uiso 1.000000 R
C5 C -0.5035(3) 0.97774(17) 0.20868(16) 0.0176(4) Uani 1.000000 .
H5 H -0.5978(3) 0.92420(17) 0.21812(16) 0.0211(5) Uiso 1.000000 R
C6 C -0.3003(3) 0.98123(16) 0.25195(15) 0.0152(4) Uani 1.000000 .
C7 C -0.2369(3) 0.90093(17) 0.30856(15) 0.0164(4) Uani 1.000000 .
H7 H -0.3314(3) 0.84455(17) 0.31367(15) 0.0197(5) Uiso 1.000000 R
C8 C 0.2056(3) 0.83557(16) 0.44349(15) 0.0152(4) Uani 1.000000 .
C9 C 0.2711(3) 0.75310(16) 0.50022(15) 0.0145(4) Uani 1.000000 .
C10 C 0.4762(3) 0.76069(16) 0.54303(15) 0.0147(4) Uani 1.000000 .
C11 C 0.5484(3) 0.68869(16) 0.60256(15) 0.0151(4) Uani 1.000000 .
C12 C 0.4184(3) 0.60577(16) 0.61541(15) 0.0148(4) Uani 1.000000 .
C13 C 0.2135(3) 0.59861(17) 0.57117(15) 0.0162(4) Uani 1.000000 .
H13 H 0.1230(3) 0.54277(17) 0.58007(15) 0.0195(5) Uiso 1.000000 R
C14 C 0.1409(3) 0.67017(17) 0.51552(15) 0.0158(4) Uani 1.000000 .
H14 H 0.0016(3) 0.66361(17) 0.48712(15) 0.0190(5) Uiso 1.000000 R
C15 C 0.4759(3) 0.52284(17) 0.67546(15) 0.0162(4) Uani 1.000000 .
C16 C 0.9243(3) 0.45603(17) 0.80470(15) 0.0168(4) Uani 1.000000 .
H16 H 1.0177(3) 0.50458(17) 0.78829(15) 0.0202(5) Uiso 1.000000 R
C17 C 0.9935(3) 0.38266(17) 0.86827(15) 0.0162(4) Uani 1.000000 .
C18 C 1.1983(3) 0.38318(17) 0.90610(16) 0.0190(4) Uani 1.000000 .
H18 H 1.2918(3) 0.43036(17) 0.88817(16) 0.0228(5) Uiso 1.000000 R
C19 C 1.2666(3) 0.31611(18) 0.96918(16) 0.0208(4) Uani 1.000000 .
H19 H 1.4057(3) 0.31742(18) 0.99451(16) 0.0249(5) Uiso 1.000000 R
C20 C 1.1293(3) 0.24678(18) 0.99502(16) 0.0221(4) Uani 1.000000 .
H20 H 1.1754(3) 0.20057(18) 1.03817(16) 0.0265(5) Uiso 1.000000 R
C21 C 0.9266(3) 0.24437(18) 0.95864(16) 0.0211(4) Uani 1.000000 .
H21 H 0.8345(3) 0.19660(18) 0.97681(16) 0.0253(5) Uiso 1.000000 R
C22 C 0.8572(3) 0.31164(17) 0.89554(16) 0.0174(4) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C1 1.364(2) . ?
O2 C8 1.236(2) . ?
O3 H3 0.8400 . ?
O3 C10 1.347(2) . ?
O4 H4 0.8400 . ?
O4 C11 1.363(2) . ?
O5 C15 1.228(2) . ?
O6 H6 0.8400 . ?
O6 C22 1.354(2) . ?
N1 N2 1.3773(19) . ?
N1 C7 1.286(2) . ?
N2 H2 0.8800 . ?
N2 C8 1.358(2) . ?
N3 H3a 0.8800 . ?
N3 N4 1.3685(19) . ?
N3 C15 1.363(2) . ?
N4 C16 1.280(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.412(2) . ?
C2 H2a 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3b 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4a 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(2) . ?
C6 C7 1.455(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.483(2) . ?
C9 C10 1.404(2) . ?
C9 C14 1.406(2) . ?
C10 C11 1.411(2) . ?
C11 C12 1.389(3) . ?
C12 C13 1.407(2) . ?
C12 C15 1.504(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(2) . ?
C14 H14 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.455(2) . ?
C17 C18 1.403(2) . ?
C17 C22 1.412(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C10 O3 H3 109.5 . . ?
C11 O4 H4 109.5 . . ?
C22 O6 H6 109.5 . . ?
C7 N1 N2 118.13(15) . . ?
H2 N2 N1 121.63(9) . . ?
C8 N2 N1 116.75(15) . . ?
C8 N2 H2 121.63(9) . . ?
N4 N3 H3a 120.79(9) . . ?
C15 N3 H3a 120.79(9) . . ?
C15 N3 N4 118.43(15) . . ?
C16 N4 N3 118.53(15) . . ?
C2 C1 O1 117.30(16) . . ?
C6 C1 O1 122.36(15) . . ?
C6 C1 C2 120.32(16) . . ?
H2a C2 C1 119.95(11) . . ?
C3 C2 C1 120.09(17) . . ?
C3 C2 H2a 119.95(10) . . ?
H3b C3 C2 119.76(10) . . ?
C4 C3 C2 120.47(16) . . ?
C4 C3 H3b 119.76(10) . . ?
H4a C4 C3 120.15(10) . . ?
C5 C4 C3 119.70(16) . . ?
C5 C4 H4a 120.15(11) . . ?
H5 C5 C4 119.51(11) . . ?
C6 C5 C4 120.97(17) . . ?
C6 C5 H5 119.51(10) . . ?
C5 C6 C1 118.42(15) . . ?
C7 C6 C1 122.25(15) . . ?
C7 C6 C5 119.33(16) . . ?
C6 C7 N1 118.87(16) . . ?
H7 C7 N1 120.57(10) . . ?
H7 C7 C6 120.57(10) . . ?
N2 C8 O2 120.72(15) . . ?
C9 C8 O2 121.64(16) . . ?
C9 C8 N2 117.64(16) . . ?
C10 C9 C8 117.36(16) . . ?
C14 C9 C8 124.18(16) . . ?
C14 C9 C10 118.44(15) . . ?
C9 C10 O3 124.45(15) . . ?
C11 C10 O3 115.05(15) . . ?
C11 C10 C9 120.49(16) . . ?
C10 C11 O4 117.98(15) . . ?
C12 C11 O4 121.60(15) . . ?
C12 C11 C10 120.42(16) . . ?
C13 C12 C11 118.34(15) . . ?
C15 C12 C11 125.78(16) . . ?
C15 C12 C13 115.86(15) . . ?
H13 C13 C12 119.13(10) . . ?
C14 C13 C12 121.75(16) . . ?
C14 C13 H13 119.13(10) . . ?
C13 C14 C9 120.51(16) . . ?
H14 C14 C9 119.74(10) . . ?
H14 C14 C13 119.74(10) . . ?
N3 C15 O5 122.75(15) . . ?
C12 C15 O5 121.62(16) . . ?
C12 C15 N3 115.63(15) . . ?
H16 C16 N4 120.21(10) . . ?
C17 C16 N4 119.58(16) . . ?
C17 C16 H16 120.21(10) . . ?
C18 C17 C16 120.38(16) . . ?
C22 C17 C16 121.12(15) . . ?
C22 C17 C18 118.48(16) . . ?
H18 C18 C17 119.42(10) . . ?
C19 C18 C17 121.17(16) . . ?
C19 C18 H18 119.42(11) . . ?
H19 C19 C18 120.36(11) . . ?
C20 C19 C18 119.29(16) . . ?
C20 C19 H19 120.36(10) . . ?
H20 C20 C19 119.61(10) . . ?
C21 C20 C19 120.79(16) . . ?
C21 C20 H20 119.61(11) . . ?
H21 C21 C20 119.91(11) . . ?
C22 C21 C20 120.18(17) . . ?
C22 C21 H21 119.91(11) . . ?
C17 C22 O6 122.18(15) . . ?
C21 C22 O6 117.73(16) . . ?
C21 C22 C17 120.09(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
