# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_KEmimTCM2
_database_code_depnum_ccdc_archive 'CCDC 1869226'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Mochida'
;Kobe University
Japan
;
_audit_update_record             
;
2018-09-23 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C8 K N6, C6 H11 N2'
_chemical_formula_sum            'C14 H11 K N8'
_chemical_formula_iupac          ?
_chemical_formula_weight         330.41

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5703(8)
_cell_length_b                   9.7142(10)
_cell_length_c                   10.2374(10)
_cell_angle_alpha                83.6370(10)
_cell_angle_beta                 83.0040(10)
_cell_angle_gamma                81.1040(10)
_cell_volume                     832.09(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4355
_cell_measurement_theta_min      2.4193
_cell_measurement_theta_max      28.8191
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340

_exptl_absorpt_coefficient_mu    0.330
_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  0.90
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4019
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             2878
_reflns_number_gt                2810
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0883
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_number_reflns         2878
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.5340P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.380
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
K K 0.2009 0.2494 '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'

_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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
K K1 0.24939(3) 0.71505(3) 0.74492(3) 0.01943(12) Uani d . . . 1 . .
N N1 1.23162(16) 0.28428(13) 0.60163(13) 0.0232(3) Uani d . . . 1 . .
C C1 1.32429(19) 0.28471(17) 0.69483(17) 0.0255(4) Uani d . . . 1 . .
H H1 1.406017 0.341322 0.69115 0.031 Uiso calc U . R 1 . .
C C2 1.12767(19) 0.18990(16) 0.64378(16) 0.0226(3) Uani d . . . 1 . .
H H2 1.047452 0.168796 0.595931 0.027 Uiso calc U . R 1 . .
N N2 1.28503(16) 0.19314(14) 0.79486(14) 0.0247(3) Uani d . . . 1 . .
C C3 1.16024(18) 0.13278(16) 0.76527(16) 0.0230(3) Uani d . . . 1 . .
H H3 1.107569 0.064502 0.819574 0.028 Uiso calc U . R 1 . .
N N3 1.03710(16) 0.51531(15) 0.79206(16) 0.0314(3) Uani d . . . 1 . .
N N4 0.51544(16) 0.51949(15) 0.80777(14) 0.0269(3) Uani d . . . 1 . .
C C4 1.2368(3) 0.37161(19) 0.47534(18) 0.0395(5) Uani d . . . 1 . .
H H4A 1.223423 0.31583 0.404425 0.059 Uiso calc U . R 1 . .
H H4B 1.339319 0.406505 0.457193 0.059 Uiso calc U . R 1 . .
H H4C 1.150979 0.450897 0.479966 0.059 Uiso calc U . R 1 . .
C C5 1.3631(2) 0.1602(2) 0.91709(19) 0.0364(4) Uani d . . . 1 . .
H H5A 1.470671 0.187954 0.90143 0.044 Uiso calc U . R 1 . .
H H5B 1.374725 0.057916 0.941776 0.044 Uiso calc U . R 1 . .
N N5 0.80853(17) 0.15787(15) 1.00125(15) 0.0305(3) Uani d . . . 1 . .
N N6 -0.02061(16) 0.88876(15) 0.67143(15) 0.0290(3) Uani d . . . 1 . .
C C6 1.2712(3) 0.2333(3) 1.0266(2) 0.0559(6) Uani d . . . 1 . .
H H6A 1.255822 0.33433 1.001005 0.084 Uiso calc U . R 1 . .
H H6B 1.329117 0.213659 1.105018 0.084 Uiso calc U . R 1 . .
H H6C 1.167562 0.20063 1.046747 0.084 Uiso calc U . R 1 . .
C C7 0.78883(17) 0.39734(16) 0.86604(15) 0.0187(3) Uani d . . . 1 . .
N N7 -0.31010(17) 1.29002(14) 0.53706(14) 0.0269(3) Uani d . . . 1 . .
N N8 -0.53313(16) 0.90397(15) 0.67739(16) 0.0298(3) Uani d . . . 1 . .
C C8 0.63908(18) 0.46507(16) 0.83415(14) 0.0198(3) Uani d . . . 1 . .
C C9 0.80027(17) 0.26508(16) 0.93913(15) 0.0204(3) Uani d . . . 1 . .
C C10 0.92616(18) 0.46143(16) 0.82568(15) 0.0215(3) Uani d . . . 1 . .
C C11 -0.29037(17) 1.03317(15) 0.63232(15) 0.0187(3) Uani d . . . 1 . .
C C12 -0.14172(18) 0.95516(16) 0.65466(15) 0.0207(3) Uani d . . . 1 . .
C C13 -0.30083(17) 1.17419(16) 0.57958(15) 0.0195(3) Uani d . . . 1 . .
C C14 -0.42568(18) 0.96441(16) 0.65563(15) 0.0206(3) 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
K1 N6 . 2.7755(14) ?
K1 N8 1_655 2.7897(14) ?
K1 N4 . 2.8228(14) ?
K1 N3 1_455 2.8247(14) ?
K1 N7 2_576 2.8748(15) ?
K1 N5 2_667 2.9547(16) ?
K1 C9 2_667 3.2339(16) ?
K1 C13 2_576 3.3743(16) ?
N1 C1 . 1.314(2) ?
N1 C2 . 1.375(2) ?
N1 C4 . 1.465(2) ?
C1 N2 . 1.327(2) ?
C1 H1 . 0.95 ?
C2 C3 . 1.348(2) ?
C2 H2 . 0.95 ?
N2 C3 . 1.375(2) ?
N2 C5 . 1.471(2) ?
C3 H3 . 0.95 ?
N3 C10 . 1.154(2) ?
N4 C8 . 1.158(2) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 C6 . 1.474(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
N5 C9 . 1.156(2) ?
N6 C12 . 1.155(2) ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 C8 . 1.407(2) ?
C7 C9 . 1.409(2) ?
C7 C10 . 1.412(2) ?
N7 C13 . 1.155(2) ?
N8 C14 . 1.154(2) ?
C11 C12 . 1.408(2) ?
C11 C14 . 1.409(2) ?
C11 C13 . 1.409(2) ?

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
N6 K1 N8 . 1_655 98.35(4) ?
N6 K1 N4 . . 174.82(4) ?
N8 K1 N4 1_655 . 85.28(4) ?
N6 K1 N3 . 1_455 82.12(4) ?
N8 K1 N3 1_655 1_455 175.15(5) ?
N4 K1 N3 . 1_455 93.96(4) ?
N6 K1 N7 . 2_576 80.85(4) ?
N8 K1 N7 1_655 2_576 77.57(4) ?
N4 K1 N7 . 2_576 96.40(4) ?
N3 K1 N7 1_455 2_576 97.77(4) ?
N6 K1 N5 . 2_667 87.19(4) ?
N8 K1 N5 1_655 2_667 84.26(4) ?
N4 K1 N5 . 2_667 96.89(4) ?
N3 K1 N5 1_455 2_667 100.59(4) ?
N7 K1 N5 2_576 2_667 156.46(4) ?
N6 K1 C9 . 2_667 100.18(4) ?
N8 K1 C9 1_655 2_667 98.46(4) ?
N4 K1 C9 . 2_667 82.86(4) ?
N3 K1 C9 1_455 2_667 86.19(4) ?
N7 K1 C9 2_576 2_667 176.02(4) ?
N5 K1 C9 2_667 2_667 20.90(4) ?
N6 K1 C13 . 2_576 69.96(4) ?
N8 K1 C13 1_655 2_576 65.00(4) ?
N4 K1 C13 . 2_576 108.60(4) ?
N3 K1 C13 1_455 2_576 110.86(4) ?
N7 K1 C13 2_576 2_576 19.25(4) ?
N5 K1 C13 2_667 2_576 137.29(4) ?
C9 K1 C13 2_667 2_576 158.07(4) ?
C1 N1 C2 . . 108.42(13) ?
C1 N1 C4 . . 125.61(14) ?
C2 N1 C4 . . 125.96(15) ?
N1 C1 N2 . . 108.84(14) ?
N1 C1 H1 . . 125.6 ?
N2 C1 H1 . . 125.6 ?
C3 C2 N1 . . 107.60(14) ?
C3 C2 H2 . . 126.2 ?
N1 C2 H2 . . 126.2 ?
C1 N2 C3 . . 108.90(14) ?
C1 N2 C5 . . 125.68(15) ?
C3 N2 C5 . . 125.41(14) ?
C2 C3 N2 . . 106.23(14) ?
C2 C3 H3 . . 126.9 ?
N2 C3 H3 . . 126.9 ?
C10 N3 K1 . 1_655 162.64(13) ?
C8 N4 K1 . . 165.24(12) ?
N1 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N2 C5 C6 . . 111.41(16) ?
N2 C5 H5A . . 109.3 ?
C6 C5 H5A . . 109.3 ?
N2 C5 H5B . . 109.3 ?
C6 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
C9 N5 K1 . 2_667 93.29(11) ?
C12 N6 K1 . . 172.02(13) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 C9 . . 119.29(13) ?
C8 C7 C10 . . 120.37(13) ?
C9 C7 C10 . . 120.34(13) ?
C13 N7 K1 . 2_576 105.62(11) ?
C14 N8 K1 . 1_455 169.10(12) ?
N4 C8 C7 . . 179.30(17) ?
N5 C9 C7 . . 178.68(17) ?
N5 C9 K1 . 2_667 65.80(10) ?
C7 C9 K1 . 2_667 112.90(10) ?
N3 C10 C7 . . 179.11(17) ?
C12 C11 C14 . . 118.42(13) ?
C12 C11 C13 . . 120.31(13) ?
C14 C11 C13 . . 121.13(13) ?
N6 C12 C11 . . 178.43(17) ?
N7 C13 C11 . . 179.55(18) ?
N7 C13 K1 . 2_576 55.14(10) ?
C11 C13 K1 . 2_576 125.25(10) ?
N8 C14 C11 . . 177.39(16) ?



####################################################################### 
# 
# 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_KEmimTCM_293K
_database_code_depnum_ccdc_archive 'CCDC 2169840'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Mochida'
;Kobe University
Japan
;
_audit_update_record             
;
2022-05-02 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 K N8'
_chemical_formula_iupac          ?
_chemical_formula_weight         330.41

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6092(12)
_cell_length_b                   9.8641(14)
_cell_length_c                   10.4829(15)
_cell_angle_alpha                83.222(2)
_cell_angle_beta                 82.672(2)
_cell_angle_gamma                81.215(2)
_cell_volume                     868.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2439
_cell_measurement_theta_min      2.7305
_cell_measurement_theta_max      27.8913
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.107
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340

_exptl_absorpt_coefficient_mu    0.317
_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  0.89
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4433
_diffrn_reflns_av_R_equivalents  0.0100
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             3222
_reflns_number_gt                2731
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1349
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         3222
_refine_ls_number_parameters     230
_refine_ls_number_restraints     38
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0646P)²+0.3520P] 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         0.337
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
K K 0.2009 0.2494 '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'

_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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
K K1 0.75470(5) 0.27225(5) 0.25922(5) 0.05801(19) Uani d . . . 1.0 . .
N N1 -0.0288(3) 0.4668(3) 0.2076(3) 0.0961(8) Uani d . . . 1.0 . .
N N2 0.1934(3) 0.8148(2) 0.0014(2) 0.0837(7) Uani d . . . 1.0 . .
N N3 0.4872(2) 0.4670(3) 0.1973(2) 0.0812(6) Uani d . . . 1.0 . .
N N4 1.3094(3) -0.2878(2) 0.4623(2) 0.0805(6) Uani d . . . 1.0 . .
N N5 1.0292(3) 0.1029(3) 0.3252(3) 0.0974(8) Uani d . . . 1.0 . .
N N6 1.5380(3) 0.0845(3) 0.3206(3) 0.0867(7) Uani d . . . 1.0 . .
C C1 0.2174(2) 0.5815(2) 0.1362(2) 0.0548(5) Uani d . . . 1.0 . .
C C2 0.0817(3) 0.5185(2) 0.1756(3) 0.0643(6) Uani d . . . 1.0 . .
C C3 0.2047(2) 0.7099(2) 0.0624(2) 0.0577(5) Uani d . . . 1.0 . .
C C4 0.3655(3) 0.5180(2) 0.1699(2) 0.0586(5) Uani d . . . 1.0 . .
C C5 1.2939(2) -0.0379(2) 0.3650(2) 0.0525(5) Uani d . . . 1.0 . .
C C6 1.3028(2) -0.1753(2) 0.4187(2) 0.0557(5) Uani d . . . 1.0 . .
C C7 1.1478(3) 0.0392(2) 0.3422(2) 0.0637(6) Uani d . . . 1.0 . .
C C8 1.4294(3) 0.0279(2) 0.3414(2) 0.0583(5) Uani d . . . 1.0 . .
N N7 0.2344(2) 0.2856(2) 0.6124(2) 0.0671(5) Uani d . . . 1.0 . .
N N8 0.2613(4) 0.2039(3) 0.8072(3) 0.0994(8) Uani d . . . 1.0 . .
C C9 0.3094(3) 0.2921(3) 0.7112(3) 0.0828(8) Uani d . . . 1.0 . .
H H9 0.384776 0.34972 0.713679 0.099 Uiso calc U . R 1.0 . .
C C10 0.1498(4) 0.1420(3) 0.7698(3) 0.0829(8) Uani d . . . 1.0 . .
H H10 0.094511 0.076626 0.819453 0.1 Uiso calc U . R 1.0 . .
C C11 0.1324(3) 0.1919(3) 0.6471(3) 0.0753(7) Uani d . . . 1.0 . .
H H11 0.063447 0.167008 0.595398 0.09 Uiso calc U . R 1.0 . .
C C12 0.2545(5) 0.3662(4) 0.4882(3) 0.1163(13) Uani d . . . 1.0 . .
H H12A 0.291831 0.305537 0.422194 0.174 Uiso calc U . R 1.0 . .
H H12B 0.330128 0.427809 0.490285 0.174 Uiso calc U . R 1.0 . .
H H12C 0.155011 0.418482 0.469742 0.174 Uiso calc U . R 1.0 . .
C C13 0.3536(14) 0.1666(9) 0.9227(8) 0.145(3) Uani d U P D 0.696(14) A 1
H H13A 0.371242 0.067433 0.943627 0.174 Uiso calc U P R 0.696(14) A 1
H H13B 0.455284 0.199984 0.905184 0.174 Uiso calc U P R 0.696(14) A 1
C C14 0.2648(14) 0.2278(13) 1.0204(9) 0.187(5) Uani d U P D 0.696(14) A 1
H H14A 0.164527 0.194051 1.036116 0.281 Uiso calc U P R 0.696(14) A 1
H H14B 0.248354 0.325729 0.998078 0.281 Uiso calc U P R 0.696(14) A 1
H H14C 0.318024 0.2073 1.096956 0.281 Uiso calc U P R 0.696(14) A 1
C C13' 0.2448(17) 0.1867(18) 0.9484(18) 0.114(5) Uani d U P D 0.304(14) A 2
H H13C 0.163208 0.257432 0.980842 0.137 Uiso calc U P R 0.304(14) A 2
H H13D 0.211298 0.097787 0.978549 0.137 Uiso calc U P R 0.304(14) A 2
C C14' 0.388(2) 0.195(3) 0.999(2) 0.158(8) Uani d U P D 0.304(14) A 2
H H14D 0.467134 0.122316 0.970571 0.237 Uiso calc U P R 0.304(14) A 2
H H14E 0.370374 0.186385 1.091435 0.237 Uiso calc U P R 0.304(14) A 2
H H14F 0.421829 0.282604 0.968259 0.237 Uiso calc U P R 0.304(14) A 2


_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
K1 N5 . 2.792(2) ?
K1 N6 1_455 2.792(2) ?
K1 N1 1_655 2.836(2) ?
K1 N3 . 2.855(2) ?
K1 N4 2_756 2.919(3) ?
K1 N2 2_665 2.920(3) ?
K1 C3 2_665 3.332(2) ?
K1 C6 2_756 3.394(2) ?
N1 C2 . 1.142(3) ?
N2 C3 . 1.148(3) ?
N3 C4 . 1.146(3) ?
N4 C6 . 1.145(3) ?
N5 C7 . 1.137(3) ?
N6 C8 . 1.146(3) ?
C1 C3 . 1.400(3) ?
C1 C2 . 1.400(3) ?
C1 C4 . 1.401(3) ?
C5 C7 . 1.399(3) ?
C5 C6 . 1.400(3) ?
C5 C8 . 1.401(3) ?
N7 C9 . 1.301(4) ?
N7 C11 . 1.358(3) ?
N7 C12 . 1.448(4) ?
N8 C9 . 1.319(4) ?
N8 C10 . 1.334(4) ?
N8 C13' . 1.460(18) ?
N8 C13 . 1.511(10) ?
C9 H9 . 0.93 ?
C10 C11 . 1.340(4) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 C14 . 1.343(11) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C13' C14' . 1.415(17) ?
C13' H13C . 0.97 ?
C13' H13D . 0.97 ?
C14' H14D . 0.96 ?
C14' H14E . 0.96 ?
C14' H14F . 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
N5 K1 N6 . 1_455 99.69(7) ?
N5 K1 N1 . 1_655 80.50(7) ?
N6 K1 N1 1_455 1_655 177.54(8) ?
N5 K1 N3 . . 174.57(8) ?
N6 K1 N3 1_455 . 85.11(7) ?
N1 K1 N3 1_655 . 94.60(7) ?
N5 K1 N4 . 2_756 83.50(8) ?
N6 K1 N4 1_455 2_756 80.33(7) ?
N1 K1 N4 1_655 2_756 97.27(8) ?
N3 K1 N4 . 2_756 94.88(7) ?
N5 K1 N2 . 2_665 90.97(8) ?
N6 K1 N2 1_455 2_665 87.64(8) ?
N1 K1 N2 1_655 2_665 94.81(8) ?
N3 K1 N2 . 2_665 91.78(7) ?
N4 K1 N2 2_756 2_665 165.68(6) ?
N5 K1 C3 . 2_665 103.25(8) ?
N6 K1 C3 1_455 2_665 100.63(7) ?
N1 K1 C3 1_655 2_665 81.69(8) ?
N3 K1 C3 . 2_665 78.19(7) ?
N4 K1 C3 2_756 2_665 172.84(6) ?
N2 K1 C3 2_665 2_665 19.79(6) ?
N5 K1 C6 . 2_756 72.97(7) ?
N6 K1 C6 1_455 2_756 67.51(7) ?
N1 K1 C6 1_655 2_756 110.30(8) ?
N3 K1 C6 . 2_756 106.86(6) ?
N4 K1 C6 2_756 2_756 19.05(5) ?
N2 K1 C6 2_665 2_756 146.84(6) ?
C3 K1 C6 2_665 2_756 166.14(6) ?
C2 N1 K1 . 1_455 163.4(2) ?
C3 N2 K1 . 2_665 100.81(19) ?
C4 N3 K1 . . 164.2(2) ?
C6 N4 K1 . 2_756 104.59(18) ?
C7 N5 K1 . . 173.8(2) ?
C8 N6 K1 . 1_655 167.7(2) ?
C3 C1 C2 . . 119.49(19) ?
C3 C1 C4 . . 119.64(19) ?
C2 C1 C4 . . 120.9(2) ?
N1 C2 C1 . . 179.8(3) ?
N2 C3 C1 . . 179.4(3) ?
N2 C3 K1 . 2_665 59.40(17) ?
C1 C3 K1 . 2_665 120.24(16) ?
N3 C4 C1 . . 179.5(3) ?
C7 C5 C6 . . 120.58(18) ?
C7 C5 C8 . . 118.66(19) ?
C6 C5 C8 . . 120.62(19) ?
N4 C6 C5 . . 179.6(3) ?
N4 C6 K1 . 2_756 56.36(16) ?
C5 C6 K1 . 2_756 123.82(15) ?
N5 C7 C5 . . 179.0(3) ?
N6 C8 C5 . . 178.2(3) ?
C9 N7 C11 . . 108.0(2) ?
C9 N7 C12 . . 125.8(3) ?
C11 N7 C12 . . 126.2(3) ?
C9 N8 C10 . . 108.7(3) ?
C9 N8 C13' . . 139.1(7) ?
C10 N8 C13' . . 107.2(6) ?
C9 N8 C13 . . 120.0(5) ?
C10 N8 C13 . . 129.9(5) ?
N7 C9 N8 . . 109.0(3) ?
N7 C9 H9 . . 125.5 ?
N8 C9 H9 . . 125.5 ?
N8 C10 C11 . . 107.1(3) ?
N8 C10 H10 . . 126.5 ?
C11 C10 H10 . . 126.5 ?
C10 C11 N7 . . 107.2(2) ?
C10 C11 H11 . . 126.4 ?
N7 C11 H11 . . 126.4 ?
N7 C12 H12A . . 109.5 ?
N7 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N7 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 N8 . . 105.8(10) ?
C14 C13 H13A . . 110.6 ?
N8 C13 H13A . . 110.6 ?
C14 C13 H13B . . 110.6 ?
N8 C13 H13B . . 110.6 ?
H13A C13 H13B . . 108.7 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C14' C13' N8 . . 112.3(17) ?
C14' C13' H13C . . 109.1 ?
N8 C13' H13C . . 109.1 ?
C14' C13' H13D . . 109.1 ?
N8 C13' H13D . . 109.1 ?
H13C C13' H13D . . 107.9 ?
C13' C14' H14D . . 109.5 ?
C13' C14' H14E . . 109.5 ?
H14D C14' H14E . . 109.5 ?
C13' C14' H14F . . 109.5 ?
H14D C14' H14F . . 109.5 ?
H14E C14' H14F . . 109.5 ?



