# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H3L
_database_code_depnum_ccdc_archive 'CCDC 1059270'
_audit_update_record             
;
2015-08-09 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H15 N3 O2), H2 O, 2(C3 H7 N1 O1)'
_chemical_formula_sum            'C46 H46 N8 O7'
_chemical_formula_weight         822.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.236(3)
_cell_length_b                   17.580(3)
_cell_length_c                   14.370(3)
_cell_angle_alpha                90
_cell_angle_beta                 126.193(4)
_cell_angle_gamma                90
_cell_volume                     3921.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.03

_exptl_crystal_description       block
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             1736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37965
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.851
_diffrn_reflns_theta_max         26.097
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3884
_reflns_number_gt                2934
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1092P)²+13.9674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3884
_refine_ls_number_parameters     243
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.2453
_refine_ls_wR_factor_gt          0.2331
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.629 0.250 -0.121 419 182 '1 dmf molecule '
2 0.129 0.750 -0.121 419 182 '1 dmf molecule '
_platon_squeeze_details          
;
 During the refinement of the structure, electron density peaks
 were located and were believed to be two highly disordered dimethylformamide
 molecules (by counting the number of electrons suppressed). All the
 attempts made to model these solvent molecules were not successful and
 they were removed using the SQUEEZE routine from PLATON (Spek, 2003).
 The reported final sum formula contains all atoms that are most possibly
 present in the crystal and thus contribute to the scattering.
;

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
C1 C 0.6677(2) 0.1662(2) 0.6920(3) 0.0378(8) Uani 1 1 d . . . . .
C2 C 0.7399(3) 0.1713(2) 0.8055(4) 0.0509(10) Uani 1 1 d . . . . .
H2 H 0.7441 0.2103 0.8524 0.061 Uiso 1 1 calc R U . . .
C3 C 0.8036(3) 0.1202(3) 0.8479(4) 0.0519(11) Uani 1 1 d . . . . .
H3 H 0.8518 0.1259 0.9238 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8017(2) 0.0600(3) 0.7860(3) 0.0477(10) Uani 1 1 d . . . . .
H4 H 0.8476 0.0260 0.8188 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7288(3) 0.0509(2) 0.6716(4) 0.0466(10) Uani 1 1 d . . . . .
H5 H 0.7243 0.0103 0.6268 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6618(2) 0.1065(2) 0.6263(3) 0.0385(9) Uani 1 1 d . . . . .
C7 C 0.5778(2) 0.09726(18) 0.5108(3) 0.0340(8) Uani 1 1 d . . . . .
C8 C 0.4463(2) 0.1282(2) 0.3652(3) 0.0369(9) Uani 1 1 d . . . . .
C9 C 0.3669(3) 0.1648(2) 0.2887(4) 0.0452(10) Uani 1 1 d . . . . .
H9 H 0.3550 0.2130 0.3026 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3061(2) 0.1220(2) 0.1882(3) 0.0440(9) Uani 1 1 d . . . . .
H10 H 0.2517 0.1420 0.1337 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3275(3) 0.0510(2) 0.1713(3) 0.0424(9) Uani 1 1 d . . . . .
H11 H 0.2872 0.0255 0.1031 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4040(3) 0.0164(2) 0.2485(3) 0.0456(10) Uani 1 1 d . . . . .
H12 H 0.4158 -0.0323 0.2360 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4627(2) 0.0567(2) 0.3455(3) 0.0388(8) Uani 1 1 d . . . . .
C14 C 0.5369(2) 0.22722(17) 0.5242(3) 0.0252(7) Uani 1 1 d . . . . .
H14 H 0.4836 0.2457 0.5106 0.030 Uiso 1 1 calc R U . . .
C15 C 0.56444(19) 0.28455(17) 0.4709(3) 0.0248(7) Uani 1 1 d . . . . .
C16 C 0.54867(18) 0.36033(17) 0.4775(2) 0.0225(6) Uani 1 1 d D . . . .
C17 C 0.56658(19) 0.41626(18) 0.4261(2) 0.0259(7) Uani 1 1 d D . . . .
C18 C 0.6051(2) 0.39591(19) 0.3731(3) 0.0310(7) Uani 1 1 d . . . . .
H18 H 0.6185 0.4330 0.3399 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6235(2) 0.3209(2) 0.3700(3) 0.0400(9) Uani 1 1 d . . . . .
H19 H 0.6506 0.3076 0.3360 0.048 Uiso 1 1 calc R U . . .
C20 C 0.6021(2) 0.26460(19) 0.4171(3) 0.0347(8) Uani 1 1 d . . . . .
H20 H 0.6131 0.2138 0.4124 0.042 Uiso 1 1 calc R U . . .
N1 N 0.6002(2) 0.21693(18) 0.6470(3) 0.0412(8) Uani 1 1 d D . . . .
N2 N 0.5479(2) 0.03796(17) 0.4407(3) 0.0400(7) Uani 1 1 d . . . . .
N3 N 0.5202(2) 0.15239(16) 0.4715(3) 0.0367(7) Uani 1 1 d . . . . .
O1 O 0.51487(16) 0.37899(12) 0.5358(2) 0.0324(6) Uani 1 1 d D . . . .
O2 O 0.54416(17) 0.48971(13) 0.4308(2) 0.0345(6) Uani 1 1 d D . . . .
O1W O 0.0000 0.0757(2) 0.2500 0.0534(10) Uani 1 2 d DS T P . .
H1N H 0.608(3) 0.251(2) 0.697(4) 0.080 Uiso 1 1 d D U . . .
H1O H 0.495(3) 0.4231(16) 0.523(4) 0.080 Uiso 1 1 d D U . . .
H1W H 0.050(2) 0.103(3) 0.292(4) 0.080 Uiso 1 1 d D U . . .
H2O H 0.535(3) 0.515(2) 0.374(3) 0.080 Uiso 1 1 d D U . . .


_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
C1 C6 1.371(6) . ?
C1 N1 1.381(5) . ?
C1 C2 1.386(6) . ?
C2 C3 1.342(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.432(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.492(5) . ?
C7 N3 1.321(5) . ?
C7 N2 1.322(4) . ?
C8 C13 1.367(5) . ?
C8 N3 1.404(4) . ?
C8 C9 1.404(6) . ?
C9 C10 1.423(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(5) . ?
C12 H12 0.9300 . ?
C13 N2 1.421(5) . ?
C14 N1 1.446(4) . ?
C14 N3 1.456(4) . ?
C14 C15 1.536(4) . ?
C14 H14 0.9800 . ?
C15 C20 1.381(4) . ?
C15 C16 1.382(4) . ?
C16 O1 1.369(4) . ?
C16 C17 1.390(4) . ?
C17 O2 1.376(4) . ?
C17 C18 1.387(4) . ?
C18 C19 1.372(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 H1N 0.88(2) . ?
O1 H1O 0.838(19) . ?
O2 H2O 0.854(19) . ?
O1W H1W 0.915(19) . ?

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
C6 C1 N1 120.0(3) . . ?
C6 C1 C2 118.6(4) . . ?
N1 C1 C2 121.4(4) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 123.8(4) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 117.6(4) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 121.6(3) . . ?
C1 C6 C7 116.4(3) . . ?
C5 C6 C7 121.6(4) . . ?
N3 C7 N2 112.0(3) . . ?
N3 C7 C6 118.7(3) . . ?
N2 C7 C6 129.2(3) . . ?
C13 C8 N3 107.1(3) . . ?
C13 C8 C9 122.5(3) . . ?
N3 C8 C9 130.4(4) . . ?
C8 C9 C10 114.5(3) . . ?
C8 C9 H9 122.8 . . ?
C10 C9 H9 122.8 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 123.6(4) . . ?
C12 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C11 C12 C13 116.6(4) . . ?
C11 C12 H12 121.7 . . ?
C13 C12 H12 121.7 . . ?
C12 C13 C8 122.4(4) . . ?
C12 C13 N2 130.7(4) . . ?
C8 C13 N2 106.8(3) . . ?
N1 C14 N3 106.9(3) . . ?
N1 C14 C15 113.7(3) . . ?
N3 C14 C15 111.7(2) . . ?
N1 C14 H14 108.2 . . ?
N3 C14 H14 108.2 . . ?
C15 C14 H14 108.2 . . ?
C20 C15 C16 119.5(3) . . ?
C20 C15 C14 124.1(3) . . ?
C16 C15 C14 116.4(3) . . ?
O1 C16 C15 118.4(3) . . ?
O1 C16 C17 120.8(3) . . ?
C15 C16 C17 120.8(3) . . ?
O2 C17 C18 123.6(3) . . ?
O2 C17 C16 117.1(3) . . ?
C18 C17 C16 119.3(3) . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.7(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.7(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C1 N1 C14 122.2(3) . . ?
C1 N1 H1N 113(4) . . ?
C14 N1 H1N 122(4) . . ?
C7 N2 C13 106.7(3) . . ?
C7 N3 C8 107.3(3) . . ?
C7 N3 C14 124.6(3) . . ?
C8 N3 C14 127.6(3) . . ?
C16 O1 H1O 114(3) . . ?
C17 O2 H2O 110(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2 0.838(19) 1.99(3) 2.737(3) 149(4) 5_666
O2 H2O O1W 0.854(19) 1.827(19) 2.674(3) 171(5) 3
O1 H1O O2 0.838(19) 1.99(3) 2.737(3) 149(4) 5_666
O2 H2O O1W 0.854(19) 1.827(19) 2.674(3) 171(5) 3

_refine_diff_density_max         0.911
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.073

