# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_L1
_database_code_depnum_ccdc_archive 'CCDC 1472401'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-06-01 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         ?
_chemical_formula_sum            'C23 H16 N4 O'
_chemical_formula_weight         364.40

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.933(4)
_cell_length_b                   7.4965(13)
_cell_length_c                   15.999(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.670(7)
_cell_angle_gamma                90
_cell_volume                     1747.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4118
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      24.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'TWINABS (Bruker, 2012/1)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3087
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.610
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3087
_reflns_number_gt                2123
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          'Refined as a 2-component twin., Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0632P)²+0.4823P] 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         3087
_refine_ls_number_parameters     266
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2761(2) 0.0304(4) 0.4177(2) 0.0401(8) Uani 1 1 d . . . . .
C2 C 0.2339(2) 0.0619(4) 0.5355(2) 0.0358(8) Uani 1 1 d . . . . .
C3 C 0.2257(2) 0.0523(4) 0.6231(2) 0.0368(8) Uani 1 1 d . . . . .
C4 C 0.2939(3) -0.0168(5) 0.6889(2) 0.0471(9) Uani 1 1 d . . . . .
H4 H 0.3497 -0.0536 0.6780 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2781(3) -0.0301(5) 0.7699(2) 0.0512(10) Uani 1 1 d . . . . .
H5 H 0.3228 -0.0745 0.8149 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1935(3) 0.0244(5) 0.7828(2) 0.0536(10) Uani 1 1 d . . . . .
H6 H 0.1829 0.0132 0.8377 0.064 Uiso 1 1 calc R U . . .
C7 C 0.1426(2) 0.1077(5) 0.6424(2) 0.0357(8) Uani 1 1 d . . . . .
C8 C 0.0689(2) 0.1792(4) 0.5754(2) 0.0371(8) Uani 1 1 d . . . . .
C9 C -0.0766(3) 0.2955(5) 0.5373(2) 0.0503(10) Uani 1 1 d . . . . .
H9 H -0.1298 0.3336 0.5532 0.060 Uiso 1 1 calc R U . . .
C10 C -0.0749(3) 0.3030(5) 0.4505(2) 0.0475(9) Uani 1 1 d . . . . .
H10 H -0.1252 0.3444 0.4100 0.057 Uiso 1 1 calc R U . . .
C11 C 0.0033(2) 0.2472(5) 0.4269(2) 0.0422(8) Uani 1 1 d . . . . .
H11 H 0.0075 0.2520 0.3698 0.051 Uiso 1 1 calc R U . . .
C12 C 0.0765(2) 0.1831(4) 0.4889(2) 0.0346(7) Uani 1 1 d . . . . .
C13 C 0.1612(2) 0.1177(4) 0.4728(2) 0.0346(8) Uani 1 1 d . . . . .
C14 C 0.3303(3) -0.0114(4) 0.3546(2) 0.0402(8) Uani 1 1 d . . . . .
C15 C 0.4178(2) -0.0896(5) 0.3827(2) 0.0473(9) Uani 1 1 d . . . . .
H15 H 0.4403 -0.1102 0.4408 0.057 Uiso 1 1 calc R U . . .
C16 C 0.4695(3) -0.1351(5) 0.3257(2) 0.0493(9) Uani 1 1 d . . . . .
H16 H 0.5264 -0.1884 0.3456 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4389(2) -0.1036(5) 0.2378(2) 0.0437(9) Uani 1 1 d . . . . .
C18 C 0.4913(3) -0.1512(5) 0.1776(2) 0.0516(10) Uani 1 1 d . . . . .
H18 H 0.5485 -0.2043 0.1962 0.062 Uiso 1 1 calc R U . . .
C19 C 0.4588(3) -0.1202(5) 0.0930(3) 0.0612(11) Uani 1 1 d . . . . .
H19 H 0.4941 -0.1529 0.0543 0.073 Uiso 1 1 calc R U . . .
C20 C 0.3725(3) -0.0391(6) 0.0624(3) 0.0618(12) Uani 1 1 d . . . . .
H20 H 0.3516 -0.0168 0.0042 0.074 Uiso 1 1 calc R U . . .
C21 C 0.3200(3) 0.0063(5) 0.1192(2) 0.0518(10) Uani 1 1 d . . . . .
H21 H 0.2629 0.0586 0.0991 0.062 Uiso 1 1 calc R U . . .
C22 C 0.3514(2) -0.0251(4) 0.2084(2) 0.0409(8) Uani 1 1 d . . . . .
C23 C 0.2982(2) 0.0199(4) 0.2682(2) 0.0397(8) Uani 1 1 d . . . . .
H23 H 0.2407 0.0713 0.2490 0.048 Uiso 1 1 calc R U . . .
N1 N 0.3063(2) 0.0083(4) 0.50120(17) 0.0413(7) Uani 1 1 d . . . . .
N2 N 0.1884(2) 0.0953(4) 0.39673(19) 0.0402(7) Uani 1 1 d D . . . .
N3 N 0.1262(2) 0.0916(4) 0.72217(17) 0.0438(7) Uani 1 1 d . . . . .
N4 N -0.00862(19) 0.2387(4) 0.59840(18) 0.0440(7) Uani 1 1 d . . . . .
O1 O 0.05401(19) 0.0272(4) 0.24988(17) 0.0552(7) Uani 1 1 d D . . . .
H1A H 0.031(3) 0.112(6) 0.214(3) 0.14(3) Uiso 1 1 d D . . . .
H1B H 0.006(3) -0.022(7) 0.263(4) 0.13(2) Uiso 1 1 d D . . . .
H2 H 0.151(2) 0.094(6) 0.3484(16) 0.060(13) Uiso 1 1 d 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
C1 N1 1.324(4) . ?
C1 N2 1.368(4) . ?
C1 C14 1.460(5) . ?
C2 C13 1.372(5) . ?
C2 N1 1.376(4) . ?
C2 C3 1.435(4) . ?
C3 C4 1.394(5) . ?
C3 C7 1.406(5) . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9300 . ?
C6 N3 1.332(5) . ?
C6 H6 0.9300 . ?
C7 N3 1.355(4) . ?
C7 C8 1.459(5) . ?
C8 N4 1.364(4) . ?
C8 C12 1.414(4) . ?
C9 N4 1.316(4) . ?
C9 C10 1.396(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.432(4) . ?
C13 N2 1.375(4) . ?
C14 C23 1.381(5) . ?
C14 C15 1.412(5) . ?
C15 C16 1.362(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.400(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.414(5) . ?
C17 C22 1.416(5) . ?
C18 C19 1.354(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.412(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.421(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.410(5) . ?
C23 H23 0.9300 . ?
N2 H2 0.850(19) . ?
O1 H1A 0.87(2) . ?
O1 H1B 0.87(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
N1 C1 N2 112.9(3) . . ?
N1 C1 C14 123.5(3) . . ?
N2 C1 C14 123.6(3) . . ?
C13 C2 N1 111.2(3) . . ?
C13 C2 C3 120.4(3) . . ?
N1 C2 C3 128.2(3) . . ?
C4 C3 C7 118.5(3) . . ?
C4 C3 C2 123.5(3) . . ?
C7 C3 C2 118.0(3) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 118.1(4) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
N3 C6 C5 124.7(3) . . ?
N3 C6 H6 117.6 . . ?
C5 C6 H6 117.6 . . ?
N3 C7 C3 122.0(3) . . ?
N3 C7 C8 117.5(3) . . ?
C3 C7 C8 120.4(3) . . ?
N4 C8 C12 120.8(3) . . ?
N4 C8 C7 118.0(3) . . ?
C12 C8 C7 121.2(3) . . ?
N4 C9 C10 125.0(3) . . ?
N4 C9 H9 117.5 . . ?
C10 C9 H9 117.5 . . ?
C11 C10 C9 117.7(4) . . ?
C11 C10 H10 121.2 . . ?
C9 C10 H10 121.2 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C8 119.1(3) . . ?
C11 C12 C13 125.2(3) . . ?
C8 C12 C13 115.6(3) . . ?
C2 C13 N2 105.7(3) . . ?
C2 C13 C12 124.1(3) . . ?
N2 C13 C12 130.2(3) . . ?
C23 C14 C15 118.9(3) . . ?
C23 C14 C1 122.2(3) . . ?
C15 C14 C1 118.9(3) . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 122.3(3) . . ?
C16 C17 C22 118.5(3) . . ?
C18 C17 C22 119.2(3) . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.4(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 119.3(4) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 121.1(4) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C17 119.3(3) . . ?
C23 C22 C21 122.1(3) . . ?
C17 C22 C21 118.6(3) . . ?
C14 C23 C22 121.0(3) . . ?
C14 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C1 N1 C2 104.0(3) . . ?
C1 N2 C13 106.2(3) . . ?
C1 N2 H2 129(3) . . ?
C13 N2 H2 123(3) . . ?
C6 N3 C7 117.1(3) . . ?
C9 N4 C8 117.9(3) . . ?
H1A O1 H1B 105(3) . . ?

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
C13 C2 C3 C4 174.5(3) . . . . ?
N1 C2 C3 C4 -0.1(6) . . . . ?
C13 C2 C3 C7 -2.3(5) . . . . ?
N1 C2 C3 C7 -176.9(3) . . . . ?
C7 C3 C4 C5 0.5(5) . . . . ?
C2 C3 C4 C5 -176.3(3) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 N3 -1.0(6) . . . . ?
C4 C3 C7 N3 -1.7(5) . . . . ?
C2 C3 C7 N3 175.3(3) . . . . ?
C4 C3 C7 C8 -179.4(3) . . . . ?
C2 C3 C7 C8 -2.4(5) . . . . ?
N3 C7 C8 N4 5.3(5) . . . . ?
C3 C7 C8 N4 -177.0(3) . . . . ?
N3 C7 C8 C12 -173.4(3) . . . . ?
C3 C7 C8 C12 4.4(5) . . . . ?
N4 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 C8 -0.8(5) . . . . ?
C10 C11 C12 C13 178.8(3) . . . . ?
N4 C8 C12 C11 -0.6(5) . . . . ?
C7 C8 C12 C11 177.9(3) . . . . ?
N4 C8 C12 C13 179.8(3) . . . . ?
C7 C8 C12 C13 -1.6(5) . . . . ?
N1 C2 C13 N2 1.1(4) . . . . ?
C3 C2 C13 N2 -174.4(3) . . . . ?
N1 C2 C13 C12 -179.3(3) . . . . ?
C3 C2 C13 C12 5.3(5) . . . . ?
C11 C12 C13 C2 177.2(3) . . . . ?
C8 C12 C13 C2 -3.2(5) . . . . ?
C11 C12 C13 N2 -3.2(6) . . . . ?
C8 C12 C13 N2 176.4(3) . . . . ?
N1 C1 C14 C23 -177.3(3) . . . . ?
N2 C1 C14 C23 3.1(5) . . . . ?
N1 C1 C14 C15 3.9(5) . . . . ?
N2 C1 C14 C15 -175.6(3) . . . . ?
C23 C14 C15 C16 -0.6(5) . . . . ?
C1 C14 C15 C16 178.2(3) . . . . ?
C14 C15 C16 C17 1.1(6) . . . . ?
C15 C16 C17 C18 -179.5(4) . . . . ?
C15 C16 C17 C22 -1.0(5) . . . . ?
C16 C17 C18 C19 179.3(4) . . . . ?
C22 C17 C18 C19 0.8(5) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C18 C19 C20 C21 -1.1(6) . . . . ?
C19 C20 C21 C22 0.7(6) . . . . ?
C16 C17 C22 C23 0.4(5) . . . . ?
C18 C17 C22 C23 179.0(3) . . . . ?
C16 C17 C22 C21 -179.7(3) . . . . ?
C18 C17 C22 C21 -1.2(5) . . . . ?
C20 C21 C22 C23 -179.7(4) . . . . ?
C20 C21 C22 C17 0.5(5) . . . . ?
C15 C14 C23 C22 0.0(5) . . . . ?
C1 C14 C23 C22 -178.7(3) . . . . ?
C17 C22 C23 C14 0.1(5) . . . . ?
C21 C22 C23 C14 -179.8(3) . . . . ?
N2 C1 N1 C2 0.1(4) . . . . ?
C14 C1 N1 C2 -179.5(3) . . . . ?
C13 C2 N1 C1 -0.7(4) . . . . ?
C3 C2 N1 C1 174.3(3) . . . . ?
N1 C1 N2 C13 0.6(4) . . . . ?
C14 C1 N2 C13 -179.8(3) . . . . ?
C2 C13 N2 C1 -1.0(4) . . . . ?
C12 C13 N2 C1 179.4(3) . . . . ?
C5 C6 N3 C7 -0.1(6) . . . . ?
C3 C7 N3 C6 1.5(5) . . . . ?
C8 C7 N3 C6 179.2(3) . . . . ?
C10 C9 N4 C8 -1.3(6) . . . . ?
C12 C8 N4 C9 1.7(5) . . . . ?
C7 C8 N4 C9 -177.0(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 H1A N3 0.87(2) 2.62(5) 3.120(4) 117(4) 4_565
O1 H1A N4 0.87(2) 2.13(3) 2.972(4) 161(6) 4_565
O1 H1B N3 0.87(2) 2.11(3) 2.961(4) 166(5) 3_556
O1 H1B N4 0.87(2) 2.74(4) 3.324(4) 126(4) 3_556
N2 H2 O1 0.850(19) 1.96(2) 2.782(4) 164(4) .

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Water/Methanol'
####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 1525513'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.
2017-06-01 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         'C23 H14 N4 O, 0.5 (C3 H7 N O), (H2 O)'

_chemical_formula_sum            'C24.50 H19.50 N4.50 O2.50'
_chemical_formula_weight         416.94

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8555(11)
_cell_length_b                   26.216(4)
_cell_length_c                   10.0748(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.799(7)
_cell_angle_gamma                90
_cell_volume                     2060.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1037
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      20.57

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9830
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.553
_diffrn_reflns_theta_max         23.307
_diffrn_reflns_theta_full        23.307
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2974
_reflns_number_gt                1678
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0082(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2974
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C23 C -0.0604(5) 0.06051(14) 0.6450(4) 0.0418(10) Uani 1 1 d . . . . .
C1 C 0.5640(5) 0.12909(14) 0.3789(4) 0.0495(11) Uani 1 1 d . . . . .
H1 H 0.5652 0.0991 0.4284 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6918(6) 0.13923(16) 0.3027(4) 0.0624(13) Uani 1 1 d . . . . .
H2 H 0.7842 0.1171 0.3026 0.075 Uiso 1 1 calc R U . . .
C3 C 0.6825(5) 0.18313(16) 0.2250(4) 0.0627(13) Uani 1 1 d . . . . .
H3 H 0.7688 0.1889 0.1710 0.075 Uiso 1 1 calc R U . . .
C4 C 0.4340(4) 0.20839(13) 0.3028(3) 0.0371(9) Uani 1 1 d . . . . .
C5 C 0.2991(5) 0.24680(13) 0.3017(3) 0.0362(9) Uani 1 1 d . . . . .
C6 C 0.1805(5) 0.32132(15) 0.2161(4) 0.0517(11) Uani 1 1 d . . . . .
H6 H 0.1812 0.3485 0.1567 0.062 Uiso 1 1 calc R U . . .
C7 C 0.0541(5) 0.32052(15) 0.3001(4) 0.0535(12) Uani 1 1 d . . . . .
H7 H -0.0258 0.3468 0.2979 0.064 Uiso 1 1 calc R U . . .
C8 C 0.0479(5) 0.28108(14) 0.3857(4) 0.0483(11) Uani 1 1 d . . . . .
H8 H -0.0376 0.2795 0.4421 0.058 Uiso 1 1 calc R U . . .
C9 C 0.1719(4) 0.24244(13) 0.3887(3) 0.0355(9) Uani 1 1 d . . . . .
C10 C 0.1754(4) 0.19758(13) 0.4693(3) 0.0349(9) Uani 1 1 d . . . . .
C11 C 0.1223(5) 0.13360(13) 0.5989(3) 0.0367(9) Uani 1 1 d . . . . .
C12 C 0.2934(5) 0.15932(12) 0.4628(3) 0.0356(9) Uani 1 1 d . . . . .
C13 C 0.4300(5) 0.16455(13) 0.3817(3) 0.0375(10) Uani 1 1 d . . . . .
C14 C 0.0360(5) 0.10223(13) 0.6923(3) 0.0367(9) Uani 1 1 d . . . . .
C15 C 0.0503(5) 0.11422(14) 0.8310(4) 0.0394(10) Uani 1 1 d . . . . .
C16 C 0.1336(5) 0.15872(15) 0.8845(4) 0.0493(11) Uani 1 1 d . . . . .
H16 H 0.1813 0.1813 0.8281 0.059 Uiso 1 1 calc R U . . .
C17 C 0.1447(5) 0.16883(17) 1.0181(4) 0.0602(12) Uani 1 1 d . . . . .
H17 H 0.1982 0.1986 1.0513 0.072 Uiso 1 1 calc R U . . .
C18 C 0.0774(6) 0.13529(19) 1.1056(4) 0.0635(13) Uani 1 1 d . . . . .
H18 H 0.0903 0.1420 1.1969 0.076 Uiso 1 1 calc R U . . .
C19 C -0.0065(5) 0.09299(18) 1.0577(4) 0.0584(12) Uani 1 1 d . . . . .
H19 H -0.0536 0.0711 1.1160 0.070 Uiso 1 1 calc R U . . .
C20 C -0.0234(5) 0.08180(14) 0.9200(4) 0.0454(10) Uani 1 1 d . . . . .
C21 C -0.1136(5) 0.03842(15) 0.8658(4) 0.0563(12) Uani 1 1 d . . . . .
H21 H -0.1615 0.0162 0.9232 0.068 Uiso 1 1 calc R U . . .
C22 C -0.1326(5) 0.02817(15) 0.7330(4) 0.0548(12) Uani 1 1 d . . . . .
H22 H -0.1938 -0.0005 0.7005 0.066 Uiso 1 1 calc R U . . .
N1 N 0.5583(4) 0.21726(12) 0.2233(3) 0.0529(10) Uani 1 1 d . . . . .
N2 N 0.3008(4) 0.28614(11) 0.2142(3) 0.0417(8) Uani 1 1 d . . . . .
N3 N 0.0682(4) 0.18057(11) 0.5573(3) 0.0389(8) Uani 1 1 d . . . . .
N4 N 0.2592(4) 0.11889(10) 0.5437(3) 0.0401(8) Uani 1 1 d . . . . .
O1 O -0.0802(3) 0.05220(9) 0.5110(2) 0.0527(8) Uani 1 1 d . . . . .
H1A H -0.1566 0.0312 0.4921 0.079 Uiso 1 1 calc R U . . .
O2 O 0.3443(3) 0.01334(9) 0.5558(3) 0.0611(9) Uani 1 1 d . . . . .
H2A H 0.3207 0.0449 0.5481 0.092 Uiso 1 1 d R U . . .
H2B H 0.4288 0.0056 0.5142 0.092 Uiso 0.5 1 d R U P . .
H2C H 0.3777 0.0101 0.6388 0.092 Uiso 0.5 1 d R U P . .
N5 N 0.5000 0.0000 1.0000 0.099(3) Uani 1 2 d S . P . .
O3 O 0.4027(18) -0.0146(6) 0.8103(10) 0.148(5) Uani 0.5 1 d . . P A -1
C24 C 0.423(3) 0.0148(10) 0.888(3) 0.128(8) Uani 0.5 1 d . . P A -1
H24 H 0.3866 0.0483 0.8731 0.153 Uiso 0.5 1 calc R U P A -1
C26 C 0.512(2) 0.0417(9) 1.100(3) 0.138(6) Uani 0.5 1 d . . P A -1
H26A H 0.5699 0.0296 1.1832 0.207 Uiso 0.5 1 calc R U P A -1
H26B H 0.5741 0.0698 1.0685 0.207 Uiso 0.5 1 calc R U P A -1
H26C H 0.3983 0.0528 1.1133 0.207 Uiso 0.5 1 calc R U P A -1
C25 C 0.547(3) -0.0477(8) 1.051(3) 0.171(11) Uani 0.5 1 d . . P A .
H25A H 0.6039 -0.0441 1.1405 0.256 Uiso 0.5 1 calc R U P . .
H25B H 0.4466 -0.0685 1.0528 0.256 Uiso 0.5 1 calc R U P . .
H25C H 0.6233 -0.0636 0.9960 0.256 Uiso 0.5 1 calc R U P . .
H3A H -0.012(4) 0.1974(12) 0.591(3) 0.030(10) Uiso 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
C23 O1 1.358(4) . ?
C23 C14 1.382(5) . ?
C23 C22 1.395(5) . ?
C1 C2 1.360(5) . ?
C1 C13 1.407(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(5) . ?
C2 H2 0.9300 . ?
C3 N1 1.322(5) . ?
C3 H3 0.9300 . ?
C4 N1 1.355(4) . ?
C4 C13 1.400(5) . ?
C4 C5 1.461(5) . ?
C5 N2 1.358(4) . ?
C5 C9 1.409(4) . ?
C6 N2 1.322(4) . ?
C6 C7 1.380(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.351(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.428(4) . ?
C10 N3 1.368(4) . ?
C10 C12 1.373(4) . ?
C11 N4 1.325(4) . ?
C11 N3 1.353(4) . ?
C11 C14 1.474(5) . ?
C12 N4 1.383(4) . ?
C12 C13 1.430(4) . ?
C14 C15 1.424(5) . ?
C15 C20 1.409(5) . ?
C15 C16 1.413(5) . ?
C16 C17 1.365(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.393(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.350(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.408(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.415(5) . ?
C21 C22 1.356(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N3 H3A 0.87(3) . ?
O1 H1A 0.8200 . ?
O2 H2A 0.8499 . ?
O2 H2B 0.8500 . ?
O2 H2C 0.8500 . ?
N5 C24 1.28(4) . ?
N5 C25 1.387(17) 3_657 ?
N5 C25 1.387(17) . ?
N5 C26 1.48(2) . ?
O3 C24 1.09(2) . ?
C24 H24 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
O1 C23 C14 117.6(3) . . ?
O1 C23 C22 121.8(4) . . ?
C14 C23 C22 120.6(4) . . ?
C2 C1 C13 119.1(4) . . ?
C2 C1 H1 120.5 . . ?
C13 C1 H1 120.5 . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
N1 C3 C2 123.9(3) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
N1 C4 C13 122.9(3) . . ?
N1 C4 C5 116.8(3) . . ?
C13 C4 C5 120.3(3) . . ?
N2 C5 C9 121.8(3) . . ?
N2 C5 C4 117.8(3) . . ?
C9 C5 C4 120.4(3) . . ?
N2 C6 C7 124.5(4) . . ?
N2 C6 H6 117.8 . . ?
C7 C6 H6 117.8 . . ?
C8 C7 C6 119.1(4) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C5 118.0(3) . . ?
C8 C9 C10 125.0(3) . . ?
C5 C9 C10 116.9(3) . . ?
N3 C10 C12 105.3(3) . . ?
N3 C10 C9 131.7(3) . . ?
C12 C10 C9 122.9(3) . . ?
N4 C11 N3 112.1(3) . . ?
N4 C11 C14 124.3(3) . . ?
N3 C11 C14 123.6(3) . . ?
C10 C12 N4 110.6(3) . . ?
C10 C12 C13 120.9(3) . . ?
N4 C12 C13 128.5(3) . . ?
C4 C13 C1 117.6(3) . . ?
C4 C13 C12 118.2(3) . . ?
C1 C13 C12 124.2(3) . . ?
C23 C14 C15 119.3(3) . . ?
C23 C14 C11 119.8(3) . . ?
C15 C14 C11 121.0(3) . . ?
C20 C15 C16 117.5(3) . . ?
C20 C15 C14 120.1(3) . . ?
C16 C15 C14 122.4(3) . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 121.1(4) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.6(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.2(4) . . ?
C19 C20 C21 122.1(4) . . ?
C15 C20 C21 117.7(4) . . ?
C22 C21 C20 122.1(4) . . ?
C22 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C3 N1 C4 117.3(3) . . ?
C6 N2 C5 117.3(3) . . ?
C11 N3 C10 107.6(3) . . ?
C11 N3 H3A 124(2) . . ?
C10 N3 H3A 128(2) . . ?
C11 N4 C12 104.4(3) . . ?
C23 O1 H1A 109.5 . . ?
H2A O2 H2B 111.2 . . ?
H2A O2 H2C 103.0 . . ?
H2B O2 H2C 107.0 . . ?
C24 N5 C25 47.1(12) . 3_657 ?
C24 N5 C25 132.9(12) . . ?
C25 N5 C25 180.0(8) 3_657 . ?
C24 N5 C26 111.2(11) . . ?
C25 N5 C26 65.2(13) 3_657 . ?
C25 N5 C26 114.8(13) . . ?
O3 C24 N5 116(3) . . ?
O3 C24 H24 122.2 . . ?
N5 C24 H24 122.2 . . ?
N5 C26 H26A 109.5 . . ?
N5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N5 C25 H25A 109.5 . . ?
N5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C13 C1 C2 C3 -2.9(6) . . . . ?
C1 C2 C3 N1 2.3(7) . . . . ?
N1 C4 C5 N2 5.0(5) . . . . ?
C13 C4 C5 N2 -174.0(3) . . . . ?
N1 C4 C5 C9 -175.3(3) . . . . ?
C13 C4 C5 C9 5.6(5) . . . . ?
N2 C6 C7 C8 -1.2(7) . . . . ?
C6 C7 C8 C9 1.1(6) . . . . ?
C7 C8 C9 C5 0.3(6) . . . . ?
C7 C8 C9 C10 -176.8(4) . . . . ?
N2 C5 C9 C8 -1.9(5) . . . . ?
C4 C5 C9 C8 178.4(3) . . . . ?
N2 C5 C9 C10 175.5(3) . . . . ?
C4 C5 C9 C10 -4.2(5) . . . . ?
C8 C9 C10 N3 0.8(6) . . . . ?
C5 C9 C10 N3 -176.4(4) . . . . ?
C8 C9 C10 C12 175.9(4) . . . . ?
C5 C9 C10 C12 -1.2(5) . . . . ?
N3 C10 C12 N4 0.8(4) . . . . ?
C9 C10 C12 N4 -175.4(3) . . . . ?
N3 C10 C12 C13 -178.4(3) . . . . ?
C9 C10 C12 C13 5.4(6) . . . . ?
N1 C4 C13 C1 1.3(5) . . . . ?
C5 C4 C13 C1 -179.7(3) . . . . ?
N1 C4 C13 C12 179.5(3) . . . . ?
C5 C4 C13 C12 -1.6(5) . . . . ?
C2 C1 C13 C4 1.2(6) . . . . ?
C2 C1 C13 C12 -176.8(4) . . . . ?
C10 C12 C13 C4 -3.8(5) . . . . ?
N4 C12 C13 C4 177.1(3) . . . . ?
C10 C12 C13 C1 174.2(4) . . . . ?
N4 C12 C13 C1 -4.9(6) . . . . ?
O1 C23 C14 C15 175.9(3) . . . . ?
C22 C23 C14 C15 -4.8(5) . . . . ?
O1 C23 C14 C11 -4.2(5) . . . . ?
C22 C23 C14 C11 175.2(3) . . . . ?
N4 C11 C14 C23 -72.5(5) . . . . ?
N3 C11 C14 C23 106.0(4) . . . . ?
N4 C11 C14 C15 107.5(4) . . . . ?
N3 C11 C14 C15 -74.0(5) . . . . ?
C23 C14 C15 C20 4.3(5) . . . . ?
C11 C14 C15 C20 -175.6(3) . . . . ?
C23 C14 C15 C16 -174.2(3) . . . . ?
C11 C14 C15 C16 5.8(5) . . . . ?
C20 C15 C16 C17 1.5(6) . . . . ?
C14 C15 C16 C17 -180.0(4) . . . . ?
C15 C16 C17 C18 1.2(7) . . . . ?
C16 C17 C18 C19 -2.7(7) . . . . ?
C17 C18 C19 C20 1.5(7) . . . . ?
C18 C19 C20 C15 1.2(6) . . . . ?
C18 C19 C20 C21 -178.6(4) . . . . ?
C16 C15 C20 C19 -2.7(5) . . . . ?
C14 C15 C20 C19 178.7(4) . . . . ?
C16 C15 C20 C21 177.2(3) . . . . ?
C14 C15 C20 C21 -1.4(5) . . . . ?
C19 C20 C21 C22 178.7(4) . . . . ?
C15 C20 C21 C22 -1.1(6) . . . . ?
C20 C21 C22 C23 0.7(6) . . . . ?
O1 C23 C22 C21 -178.4(4) . . . . ?
C14 C23 C22 C21 2.3(6) . . . . ?
C2 C3 N1 C4 0.2(7) . . . . ?
C13 C4 N1 C3 -2.0(6) . . . . ?
C5 C4 N1 C3 179.0(4) . . . . ?
C7 C6 N2 C5 -0.3(6) . . . . ?
C9 C5 N2 C6 1.8(5) . . . . ?
C4 C5 N2 C6 -178.5(3) . . . . ?
N4 C11 N3 C10 0.3(4) . . . . ?
C14 C11 N3 C10 -178.4(3) . . . . ?
C12 C10 N3 C11 -0.7(4) . . . . ?
C9 C10 N3 C11 175.1(4) . . . . ?
N3 C11 N4 C12 0.3(4) . . . . ?
C14 C11 N4 C12 178.9(3) . . . . ?
C10 C12 N4 C11 -0.7(4) . . . . ?
C13 C12 N4 C11 178.5(4) . . . . ?
C25 N5 C24 O3 171(3) 3_657 . . . ?
C25 N5 C24 O3 -9(3) . . . . ?
C26 N5 C24 O3 -176.6(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.82 1.90 2.716(4) 175.8 3_556
O2 H2A N4 0.85 2.00 2.846(4) 175.6 .
O2 H2B O2 0.85 2.05 2.896(5) 170.6 3_656
O2 H2C O3 0.85 1.83 2.654(11) 161.4 .
C25 H25A O3 0.96 1.62 2.15(3) 110.7 3_657
N3 H3A N1 0.87(3) 2.63(3) 3.163(4) 121(2) 4_566
N3 H3A N2 0.87(3) 2.08(3) 2.909(4) 159(3) 4_566

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF/Water'
_exptl_crystal_preparation       ', Luminescent'
