# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_tk02_06_25_2013_0m
_database_code_depnum_ccdc_archive 'CCDC 1487705'
_audit_update_record             
;
2016-10-20 deposited with the CCDC.
2016-10-21 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         ' C18 H15 N5 O, C2 H6 O'
_chemical_formula_sum            'C20 H21 N5 O2'
_chemical_formula_weight         363.42

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.8827(10)
_cell_length_b                   16.544(2)
_cell_length_c                   17.510(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1993.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    188(2)
_cell_measurement_reflns_used    1830
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      24.40

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      188(2)
_diffrn_radiation_wavelength     0.71073
_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            16132
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.693
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_full        25.045
_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             3535
_reflns_number_gt                2383
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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)+(0.1000P)²+0.1000P] 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       .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3535
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_restrained_S_all      0.862
_refine_ls_shift/su_max          0.000
_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
O1 O 0.6833(5) 0.64289(14) 0.04330(14) 0.0389(7) Uani 1 1 d . . . . .
O2 O 0.6721(7) 0.3083(3) 0.7932(2) 0.0802(12) Uani 1 1 d . . . . .
N1 N 0.6859(5) 0.31611(17) -0.04172(17) 0.0354(8) Uani 1 1 d . . . . .
H1 H 0.6830 0.3072 -0.0913 0.042 Uiso 1 1 calc R U . . .
N2 N 0.6864(6) 0.39039(18) -0.01578(19) 0.0356(8) Uani 1 1 d . . . . .
N3 N 0.6812(8) 0.8560(2) 0.0632(2) 0.0534(10) Uani 1 1 d . . . . .
N4 N 0.6509(7) 0.8091(2) -0.1789(2) 0.0565(11) Uani 1 1 d . . . . .
N5 N 0.6846(8) 0.6003(3) -0.2267(2) 0.0665(12) Uani 1 1 d . . . . .
C1 C 0.6916(9) 0.0481(2) 0.1646(3) 0.0579(13) Uani 1 1 d . . . . .
H1A H 0.7343 -0.0008 0.1378 0.087 Uiso 1 1 calc R U . . .
H1B H 0.5597 0.0400 0.1842 0.087 Uiso 1 1 calc R U . . .
H1C H 0.7800 0.0592 0.2072 0.087 Uiso 1 1 calc R U . . .
C2 C 0.6930(8) 0.1188(2) 0.1100(2) 0.0407(10) Uani 1 1 d . . . . .
C3 C 0.6791(7) 0.1077(2) 0.0316(2) 0.0424(10) Uani 1 1 d . . . . .
H3 H 0.6710 0.0544 0.0118 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6767(7) 0.1725(2) -0.0184(2) 0.0384(9) Uani 1 1 d . . . . .
H4 H 0.6659 0.1633 -0.0718 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7075(7) 0.1983(2) 0.1362(2) 0.0439(11) Uani 1 1 d . . . . .
H5 H 0.7187 0.2076 0.1895 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7061(7) 0.2636(2) 0.0877(2) 0.0407(11) Uani 1 1 d . . . . .
H6 H 0.7161 0.3170 0.1074 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6898(7) 0.2507(2) 0.0093(2) 0.0341(9) Uani 1 1 d . . . . .
C8 C 0.6856(6) 0.4499(2) -0.0652(2) 0.0368(9) Uani 1 1 d . . . . .
H8 H 0.6868 0.4398 -0.1186 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6830(7) 0.5297(2) -0.0364(2) 0.0345(9) Uani 1 1 d . . . . .
C10 C 0.6836(7) 0.5530(2) 0.0470(2) 0.0367(9) Uani 1 1 d . . . . .
C11 C 0.4978(7) 0.5291(3) 0.0890(3) 0.0455(12) Uani 1 1 d . . . . .
H11A H 0.4958 0.5548 0.1394 0.068 Uiso 1 1 calc R U . . .
H11B H 0.4937 0.4702 0.0950 0.068 Uiso 1 1 calc R U . . .
H11C H 0.3847 0.5469 0.0594 0.068 Uiso 1 1 calc R U . . .
C12 C 0.8664(6) 0.5293(3) 0.0902(3) 0.0462(12) Uani 1 1 d . . . . .
H12A H 0.9808 0.5488 0.0625 0.069 Uiso 1 1 calc R U . . .
H12B H 0.8727 0.4703 0.0947 0.069 Uiso 1 1 calc R U . . .
H12C H 0.8637 0.5534 0.1413 0.069 Uiso 1 1 calc R U . . .
C13 C 0.6810(7) 0.5994(2) -0.0797(2) 0.0337(9) Uani 1 1 d . . . . .
C14 C 0.6800(7) 0.6675(2) -0.0293(2) 0.0337(9) Uani 1 1 d . . . . .
C15 C 0.6775(7) 0.7489(2) -0.0441(2) 0.0348(9) Uani 1 1 d . . . . .
C16 C 0.6794(7) 0.8068(2) 0.0168(2) 0.0374(9) Uani 1 1 d . . . . .
C17 C 0.6638(7) 0.7808(2) -0.1191(2) 0.0391(10) Uani 1 1 d . . . . .
C18 C 0.6807(8) 0.6013(2) -0.1612(3) 0.0428(10) Uani 1 1 d . . . . .
C20 C 0.8222(11) 0.1807(5) 0.7613(3) 0.100(2) Uani 1 1 d . . . . .
H20C H 0.9093 0.1546 0.7245 0.150 Uiso 1 1 calc R U . . .
H20B H 0.8776 0.1764 0.8127 0.150 Uiso 1 1 calc R U . . .
H20A H 0.6951 0.1540 0.7601 0.150 Uiso 1 1 calc R U . . .
C19 C 0.7984(10) 0.2686(5) 0.7405(3) 0.090(2) Uani 1 1 d . . . . .
H19B H 0.9270 0.2954 0.7409 0.108 Uiso 1 1 calc R U . . .
H19A H 0.7443 0.2729 0.6883 0.108 Uiso 1 1 calc R U . . .
H2 H 0.542(12) 0.306(5) 0.776(4) 0.13(3) 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
O1 C14 1.336(4) . ?
O1 C10 1.489(4) . ?
O2 C19 1.427(7) . ?
O2 H2 0.95(8) . ?
N1 N2 1.310(4) . ?
N1 C7 1.404(5) . ?
N1 H1 0.8800 . ?
N2 C8 1.312(5) . ?
N3 C16 1.150(5) . ?
N4 C17 1.151(5) . ?
N5 C18 1.148(5) . ?
C1 C2 1.511(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.388(6) . ?
C2 C5 1.396(6) . ?
C3 C4 1.383(5) . ?
C3 H3 0.9500 . ?
C4 C7 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(5) . ?
C6 H6 0.9500 . ?
C8 C9 1.413(5) . ?
C8 H8 0.9500 . ?
C9 C13 1.380(5) . ?
C9 C10 1.510(5) . ?
C10 C12 1.520(6) . ?
C10 C11 1.527(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.427(6) . ?
C13 C14 1.432(5) . ?
C14 C15 1.372(5) . ?
C15 C17 1.417(6) . ?
C15 C16 1.434(6) . ?
C20 C19 1.507(10) . ?
C20 H20C 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20A 0.9800 . ?
C19 H19B 0.9900 . ?
C19 H19A 0.9900 . ?

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
C14 O1 C10 110.3(3) . . ?
C19 O2 H2 111(4) . . ?
N2 N1 C7 120.1(3) . . ?
N2 N1 H1 119.9 . . ?
C7 N1 H1 119.9 . . ?
N1 N2 C8 118.4(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C5 117.0(4) . . ?
C3 C2 C1 121.6(4) . . ?
C5 C2 C1 121.4(4) . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C7 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
C7 C4 H4 119.9 . . ?
C6 C5 C2 122.5(4) . . ?
C6 C5 H5 118.8 . . ?
C2 C5 H5 118.8 . . ?
C5 C6 C7 119.2(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C4 C7 C6 119.6(4) . . ?
C4 C7 N1 119.7(3) . . ?
C6 C7 N1 120.7(3) . . ?
N2 C8 C9 117.8(3) . . ?
N2 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C13 C9 C8 125.7(3) . . ?
C13 C9 C10 108.6(3) . . ?
C8 C9 C10 125.7(3) . . ?
O1 C10 C9 102.3(3) . . ?
O1 C10 C12 106.3(3) . . ?
C9 C10 C12 114.7(4) . . ?
O1 C10 C11 106.1(4) . . ?
C9 C10 C11 113.4(4) . . ?
C12 C10 C11 112.8(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C18 124.6(3) . . ?
C9 C13 C14 108.6(3) . . ?
C18 C13 C14 126.7(4) . . ?
O1 C14 C15 118.7(3) . . ?
O1 C14 C13 110.3(3) . . ?
C15 C14 C13 131.0(3) . . ?
C14 C15 C17 122.8(3) . . ?
C14 C15 C16 121.0(3) . . ?
C17 C15 C16 116.2(3) . . ?
N3 C16 C15 176.9(4) . . ?
N4 C17 C15 177.6(4) . . ?
N5 C18 C13 177.4(5) . . ?
C19 C20 H20C 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
O2 C19 C20 110.8(6) . . ?
O2 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
O2 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
H19B C19 H19A 108.1 . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.037

