# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_TK287b
_database_code_depnum_ccdc_archive 'CCDC 2049506'
loop_
_audit_author_name
_audit_author_address
'Gerald Draeger'
;Leibniz University Hannover, Institute of organic Chemistry
Germany
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            tk287
_chemical_formula_moiety         'C18 H19 N9 O2'
_chemical_formula_sum            'C18 H19 N9 O2'
_chemical_formula_iupac          'C18 H19 N9 O2'
_chemical_formula_weight         393.42
_chemical_absolute_configuration rm

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.7974(12)
_cell_length_b                   13.920(2)
_cell_length_c                   9.9497(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.655(6)
_cell_angle_gamma                90
_cell_volume                     941.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6041
_cell_measurement_theta_min      2.5133
_cell_measurement_theta_max      27.3247
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'φ and ω scan'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            21262
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         27.80
_diffrn_reflns_theta_full        27.80
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             4350
_reflns_number_gt                3248
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1413
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_restrained_S_all      0.866
_refine_ls_number_reflns         4350
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1197 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O001 0.5429(4) 0.22695(19) 0.3113(3) 0.0538(7) Uani d . . . 1 . .
N N1 0.8431(4) 0.2987(2) 0.4374(3) 0.0457(8) Uani d . . . 1 . .
O O002 0.3184(5) 0.8966(2) -0.0794(3) 0.0643(8) Uani d . . . 1 . .
N N2 0.2272(5) 0.1723(3) 0.1796(4) 0.0583(9) Uani d . . . 1 . .
N N4 0.1301(4) 0.5106(2) 0.5043(4) 0.0464(8) Uani d . . . 1 . .
N N3 0.1996(6) 0.2579(3) 0.1534(4) 0.0614(10) Uani d . . . 1 . .
N N005 0.7421(4) 0.3706(2) 0.4600(3) 0.0505(8) Uani d . . . 1 . .
N N006 0.1455(4) 0.5455(2) 0.3914(3) 0.0448(7) Uani d . . . 1 . .
C C009 0.1894(5) 0.6066(3) 0.1059(4) 0.0401(8) Uani d . . . 1 . .
H H00A 0.157837 0.55087 0.050885 0.048 Uiso calc U . R 1 . .
H H00B 0.073675 0.622769 0.156071 0.048 Uiso calc U . R 1 . .
C C00A 0.3838(6) 0.8645(3) 0.0254(4) 0.0472(9) Uani d . . . 1 . .
C C00B 0.3597(4) 0.5810(2) 0.2055(3) 0.0326(7) Uani d . . . 1 . .
H H00C 0.466272 0.555149 0.152028 0.039 Uiso calc U . R 1 . .
C C00C 0.5647(4) 0.3874(3) 0.3851(3) 0.0345(7) Uani d . . . 1 . .
C C00D 0.4448(4) 0.6681(2) 0.2834(3) 0.0339(7) Uani d . . . 1 . .
H H00D 0.344529 0.691504 0.34416 0.041 Uiso calc U . R 1 . .
C C00E 0.2879(5) 0.3294(2) 0.2345(3) 0.0402(8) Uani d . . . 1 . .
C C00F 0.4895(4) 0.7473(2) 0.1850(3) 0.0357(7) Uani d . . . 1 . .
H H00F 0.583671 0.720349 0.122456 0.043 Uiso calc U . R 1 . .
C C00G 0.4730(5) 0.3078(3) 0.3101(4) 0.0376(7) Uani d . . . 1 . .
C C00H 0.3071(5) 0.7770(2) 0.0988(4) 0.0385(7) Uani d . . . 1 . .
C C00I 0.2403(5) 0.6911(3) 0.0144(4) 0.0444(9) Uani d . . . 1 . .
H H00E 0.344292 0.672312 -0.044998 0.053 Uiso calc U . R 1 . .
H H00G 0.125676 0.708538 -0.040648 0.053 Uiso calc U . R 1 . .
C C00J 0.3015(4) 0.5001(2) 0.3069(3) 0.0342(7) Uani d . . . 1 . .
C C00K 0.4852(4) 0.4756(3) 0.3900(3) 0.0340(7) Uani d . . . 1 . .
C C00L 0.2087(5) 0.4164(2) 0.2360(4) 0.0404(8) Uani d . . . 1 . .
H H00L 0.08895 0.425834 0.19033 0.049 Uiso calc U . R 1 . .
N N00M 0.9577(5) 0.2411(3) 0.4351(4) 0.0691(11) Uani d . . . 1 . .
C C00N 0.5794(5) 0.5575(3) 0.4648(4) 0.0422(8) Uani d . . . 1 . .
H H00H 0.699616 0.535739 0.510072 0.051 Uiso calc U . R 1 . .
H H00I 0.491257 0.580824 0.532472 0.051 Uiso calc U . R 1 . .
N N00O 0.1039(5) 0.4863(4) 0.6101(4) 0.0741(12) Uani d . . . 1 . .
C C00P 0.6264(5) 0.6385(3) 0.3682(4) 0.0415(8) Uani d . . . 1 . .
H H00J 0.729389 0.617834 0.309295 0.05 Uiso calc U . R 1 . .
H H00K 0.674857 0.693516 0.419002 0.05 Uiso calc U . R 1 . .
C C00Q 0.5549(6) 0.9066(3) 0.1095(5) 0.0555(10) Uani d . . . 1 . .
H H00M 0.674803 0.905973 0.058976 0.067 Uiso calc U . R 1 . .
H H00N 0.526495 0.972238 0.135097 0.067 Uiso calc U . R 1 . .
C C00R 0.5768(5) 0.8429(3) 0.2335(4) 0.0475(9) Uani d . . . 1 . .
H H00O 0.504145 0.868786 0.307807 0.057 Uiso calc U . R 1 . .
H H00P 0.714021 0.835788 0.261304 0.057 Uiso calc U . R 1 . .
C C00S 0.1375(5) 0.8171(3) 0.1823(4) 0.0492(9) Uani d . . . 1 . .
H H00Q 0.02933 0.834733 0.123209 0.074 Uiso calc U . R 1 . .
H H00R 0.182551 0.872671 0.231397 0.074 Uiso calc U . R 1 . .
H H00S 0.09537 0.768917 0.244146 0.074 Uiso calc U . R 1 . .
N N00T 0.2278(8) 0.0926(3) 0.1862(7) 0.0926(16) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O001 C00G . 1.222(4) ?
N1 N00M . 1.118(5) ?
N1 N005 . 1.239(4) ?
O002 C00A . 1.208(5) ?
N2 N00T . 1.111(6) ?
N2 N3 . 1.233(5) ?
N4 N00O . 1.125(5) ?
N4 N006 . 1.232(5) ?
N3 C00E . 1.405(5) ?
N005 C00C . 1.418(4) ?
N006 C00J . 1.510(4) ?
C009 C00I . 1.533(5) ?
C009 C00B . 1.543(4) ?
C009 H00A . 0.97 ?
C009 H00B . 0.97 ?
C00A C00H . 1.521(5) ?
C00A C00Q . 1.529(6) ?
C00B C00D . 1.542(4) ?
C00B C00J . 1.571(5) ?
C00B H00C . 0.98 ?
C00C C00K . 1.343(5) ?
C00C C00G . 1.464(5) ?
C00D C00F . 1.512(5) ?
C00D C00P . 1.531(4) ?
C00D H00D . 0.98 ?
C00E C00L . 1.326(5) ?
C00E C00G . 1.478(5) ?
C00F C00R . 1.530(5) ?
C00F C00H . 1.543(4) ?
C00F H00F . 0.98 ?
C00H C00I . 1.523(5) ?
C00H C00S . 1.545(5) ?
C00I H00E . 0.97 ?
C00I H00G . 0.97 ?
C00J C00L . 1.492(5) ?
C00J C00K . 1.516(4) ?
C00K C00N . 1.495(5) ?
C00L H00L . 0.93 ?
C00N C00P . 1.521(5) ?
C00N H00H . 0.97 ?
C00N H00I . 0.97 ?
C00P H00J . 0.97 ?
C00P H00K . 0.97 ?
C00Q C00R . 1.523(6) ?
C00Q H00M . 0.97 ?
C00Q H00N . 0.97 ?
C00R H00O . 0.97 ?
C00R H00P . 0.97 ?
C00S H00Q . 0.96 ?
C00S H00R . 0.96 ?
C00S H00S . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N00M N1 N005 . . 166.7(4) ?
N00T N2 N3 . . 167.8(5) ?
N00O N4 N006 . . 173.0(4) ?
N2 N3 C00E . . 120.2(3) ?
N1 N005 C00C . . 120.3(3) ?
N4 N006 C00J . . 115.0(3) ?
C00I C009 C00B . . 112.4(3) ?
C00I C009 H00A . . 109.1 ?
C00B C009 H00A . . 109.1 ?
C00I C009 H00B . . 109.1 ?
C00B C009 H00B . . 109.1 ?
H00A C009 H00B . . 107.9 ?
O002 C00A C00H . . 126.0(4) ?
O002 C00A C00Q . . 125.9(4) ?
C00H C00A C00Q . . 108.1(3) ?
C00D C00B C009 . . 113.9(3) ?
C00D C00B C00J . . 109.8(3) ?
C009 C00B C00J . . 112.3(2) ?
C00D C00B H00C . . 106.8 ?
C009 C00B H00C . . 106.8 ?
C00J C00B H00C . . 106.8 ?
C00K C00C N005 . . 117.9(3) ?
C00K C00C C00G . . 123.0(3) ?
N005 C00C C00G . . 119.1(3) ?
C00F C00D C00P . . 112.3(3) ?
C00F C00D C00B . . 109.1(3) ?
C00P C00D C00B . . 110.5(3) ?
C00F C00D H00D . . 108.3 ?
C00P C00D H00D . . 108.3 ?
C00B C00D H00D . . 108.3 ?
C00L C00E N3 . . 119.1(3) ?
C00L C00E C00G . . 121.3(3) ?
N3 C00E C00G . . 119.5(3) ?
C00D C00F C00R . . 120.9(3) ?
C00D C00F C00H . . 112.5(2) ?
C00R C00F C00H . . 103.9(3) ?
C00D C00F H00F . . 106.2 ?
C00R C00F H00F . . 106.2 ?
C00H C00F H00F . . 106.2 ?
O001 C00G C00C . . 122.2(3) ?
O001 C00G C00E . . 121.1(3) ?
C00C C00G C00E . . 116.7(3) ?
C00A C00H C00I . . 117.8(3) ?
C00A C00H C00F . . 101.5(3) ?
C00I C00H C00F . . 108.5(3) ?
C00A C00H C00S . . 103.9(3) ?
C00I C00H C00S . . 111.4(3) ?
C00F C00H C00S . . 113.4(3) ?
C00H C00I C009 . . 110.1(3) ?
C00H C00I H00E . . 109.6 ?
C009 C00I H00E . . 109.6 ?
C00H C00I H00G . . 109.6 ?
C009 C00I H00G . . 109.6 ?
H00E C00I H00G . . 108.2 ?
C00L C00J N006 . . 107.2(3) ?
C00L C00J C00K . . 114.4(3) ?
N006 C00J C00K . . 111.8(3) ?
C00L C00J C00B . . 111.5(3) ?
N006 C00J C00B . . 104.6(2) ?
C00K C00J C00B . . 107.0(2) ?
C00C C00K C00N . . 123.2(3) ?
C00C C00K C00J . . 120.8(3) ?
C00N C00K C00J . . 115.7(3) ?
C00E C00L C00J . . 123.5(3) ?
C00E C00L H00L . . 118.2 ?
C00J C00L H00L . . 118.2 ?
C00K C00N C00P . . 110.2(3) ?
C00K C00N H00H . . 109.6 ?
C00P C00N H00H . . 109.6 ?
C00K C00N H00I . . 109.6 ?
C00P C00N H00I . . 109.6 ?
H00H C00N H00I . . 108.1 ?
C00N C00P C00D . . 111.6(3) ?
C00N C00P H00J . . 109.3 ?
C00D C00P H00J . . 109.3 ?
C00N C00P H00K . . 109.3 ?
C00D C00P H00K . . 109.3 ?
H00J C00P H00K . . 108.0 ?
C00R C00Q C00A . . 106.0(3) ?
C00R C00Q H00M . . 110.5 ?
C00A C00Q H00M . . 110.5 ?
C00R C00Q H00N . . 110.5 ?
C00A C00Q H00N . . 110.5 ?
H00M C00Q H00N . . 108.7 ?
C00Q C00R C00F . . 102.8(3) ?
C00Q C00R H00O . . 111.2 ?
C00F C00R H00O . . 111.2 ?
C00Q C00R H00P . . 111.2 ?
C00F C00R H00P . . 111.2 ?
H00O C00R H00P . . 109.1 ?
C00H C00S H00Q . . 109.5 ?
C00H C00S H00R . . 109.5 ?
H00Q C00S H00R . . 109.5 ?
C00H C00S H00S . . 109.5 ?
H00Q C00S H00S . . 109.5 ?
H00R C00S H00S . . 109.5 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, petrol ether'
