# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_161031b-62_a
_database_code_depnum_ccdc_archive 'CCDC 1566725'
loop_
_audit_author_name
_audit_author_address
'Zhiqiang Guo'
;Shanxi University
China
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-04-08 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            'C13 H21 K N2 O'
_chemical_formula_weight         260.42

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   12.2184(8)
_cell_length_b                   7.5854(5)
_cell_length_c                   15.6270(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1448.33(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3384
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      26.42

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.355
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   sadabs
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10514
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_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             1385
_reflns_number_gt                1031
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0673P)²+3.8045P] 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         1385
_refine_ls_number_parameters     103
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.057
_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
K1 K 0.5000 0.5000 0.5000 0.0310(4) Uani 1 2 d S . P . .
O1 O 0.3397(3) 0.2500 0.5462(2) 0.0414(10) Uani 1 2 d S T P . .
N2 N 0.5724(3) 0.2500 0.3722(2) 0.0281(10) Uani 1 2 d S T P . .
N1 N 0.6579(3) 0.2500 0.5476(3) 0.0330(10) Uani 1 2 d S T P . .
C5 C 0.6755(4) 0.2500 0.3897(3) 0.0273(11) Uani 1 2 d S T P . .
C6 C 0.5350(4) 0.2500 0.2822(3) 0.0357(13) Uani 1 2 d S T P . .
C4 C 0.7201(4) 0.2500 0.4743(3) 0.0276(11) Uani 1 2 d S T P . .
C1 C 0.7311(4) 0.2500 0.6123(3) 0.0382(13) Uani 1 2 d S T P . .
H1 H 0.7113 0.2500 0.6711 0.046 Uiso 1 2 calc R U P . .
C3 C 0.8320(4) 0.2500 0.4950(4) 0.0403(14) Uani 1 2 d S T P . .
H3 H 0.8916 0.2500 0.4560 0.048 Uiso 1 2 calc R U P . .
C13 C 0.2536(4) 0.2500 0.4834(4) 0.0452(15) Uani 1 2 d S T P . .
H13A H 0.2591 0.1440 0.4466 0.054 Uiso 0.5 1 calc R U P . .
H13B H 0.2591 0.3560 0.4466 0.054 Uiso 0.5 1 calc R U P . .
C2 C 0.8382(4) 0.2500 0.5834(4) 0.0449(15) Uani 1 2 d S T P . .
H2 H 0.9027 0.2500 0.6174 0.054 Uiso 1 2 calc R U P . .
C12 C 0.1461(5) 0.2500 0.5315(5) 0.0544(15) Uani 1 2 d S TU P . .
H12A H 0.1026 0.3562 0.5175 0.065 Uiso 0.5 1 calc R U P . .
H12B H 0.1026 0.1438 0.5175 0.065 Uiso 0.5 1 calc R U P . .
C7 C 0.4619(4) 0.0865(7) 0.2720(3) 0.0618(14) Uani 1 1 d . . . . .
H7A H 0.4348 0.0803 0.2131 0.093 Uiso 1 1 calc R U . . .
H7B H 0.5046 -0.0196 0.2849 0.093 Uiso 1 1 calc R U . . .
H7C H 0.3999 0.0947 0.3115 0.093 Uiso 1 1 calc R U . . .
C8 C 0.6225(6) 0.2500 0.2148(4) 0.082(3) Uani 1 2 d S T P . .
H8A H 0.5886 0.2500 0.1580 0.122 Uiso 1 2 calc R U P . .
H8B H 0.6681 0.3555 0.2212 0.122 Uiso 0.5 1 calc R U P . .
H8C H 0.6681 0.1445 0.2212 0.122 Uiso 0.5 1 calc R U P . .
C10 C 0.2914(6) 0.2500 0.6292(4) 0.069(2) Uani 1 2 d S TU P . .
H10A H 0.3152 0.1442 0.6613 0.082 Uiso 0.5 1 calc R U P . .
H10B H 0.3152 0.3558 0.6613 0.082 Uiso 0.5 1 calc R U P . .
C11 C 0.1778(6) 0.2500 0.6206(5) 0.0774(18) Uani 1 2 d S TU P . .
H11A H 0.1472 0.3556 0.6492 0.093 Uiso 0.5 1 calc R U P . .
H11B H 0.1472 0.1444 0.6492 0.093 Uiso 0.5 1 calc R U P . .
H5 H 0.737(4) 0.2500 0.345(4) 0.042(16) Uiso 1 2 d S . P . .


_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
K1 N1 2.806(3) 5_666 ?
K1 N1 2.806(3) . ?
K1 O1 2.821(3) 5_666 ?
K1 O1 2.821(3) . ?
K1 N2 2.893(3) 5_666 ?
K1 N2 2.893(3) . ?
K1 C4 3.315(4) 5_666 ?
K1 C5 3.342(4) 5_666 ?
K1 K1 3.7927(3) 3_646 ?
K1 K1 3.7927(3) 3_656 ?
O1 C10 1.424(7) . ?
O1 C13 1.439(6) . ?
O1 K1 2.821(3) 3_646 ?
N2 C5 1.288(6) . ?
N2 C6 1.479(6) . ?
N2 K1 2.893(3) 3_646 ?
N1 C1 1.350(6) . ?
N1 C4 1.375(6) . ?
N1 K1 2.806(3) 3_646 ?
C5 C4 1.430(7) . ?
C5 K1 3.342(4) 3_646 ?
C5 H5 1.03(6) . ?
C6 C8 1.501(8) . ?
C6 C7 1.536(6) 7_565 ?
C6 C7 1.536(6) . ?
C4 C3 1.405(7) . ?
C4 K1 3.315(4) 3_646 ?
C1 C2 1.384(8) . ?
C1 H1 0.9500 . ?
C3 C2 1.384(8) . ?
C3 H3 0.9500 . ?
C13 C12 1.514(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C2 H2 0.9500 . ?
C12 C11 1.445(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 C11 1.395(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 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
N1 K1 N1 180.0 5_666 . ?
N1 K1 O1 87.44(8) 5_666 5_666 ?
N1 K1 O1 92.56(8) . 5_666 ?
N1 K1 O1 92.56(8) 5_666 . ?
N1 K1 O1 87.44(8) . . ?
O1 K1 O1 180.0 5_666 . ?
N1 K1 N2 61.93(11) 5_666 5_666 ?
N1 K1 N2 118.07(11) . 5_666 ?
O1 K1 N2 87.06(8) 5_666 5_666 ?
O1 K1 N2 92.94(8) . 5_666 ?
N1 K1 N2 118.07(11) 5_666 . ?
N1 K1 N2 61.93(11) . . ?
O1 K1 N2 92.94(8) 5_666 . ?
O1 K1 N2 87.06(8) . . ?
N2 K1 N2 180.0 5_666 . ?
N1 K1 C4 24.16(12) 5_666 5_666 ?
N1 K1 C4 155.84(12) . 5_666 ?
O1 K1 C4 102.12(7) 5_666 5_666 ?
O1 K1 C4 77.88(7) . 5_666 ?
N2 K1 C4 45.02(11) 5_666 5_666 ?
N2 K1 C4 134.98(11) . 5_666 ?
N1 K1 C5 46.52(11) 5_666 5_666 ?
N1 K1 C5 133.48(11) . 5_666 ?
O1 K1 C5 101.32(7) 5_666 5_666 ?
O1 K1 C5 78.68(7) . 5_666 ?
N2 K1 C5 22.40(11) 5_666 5_666 ?
N2 K1 C5 157.60(11) . 5_666 ?
C4 K1 C5 24.81(12) 5_666 5_666 ?
N1 K1 K1 132.53(6) 5_666 3_646 ?
N1 K1 K1 47.47(5) . 3_646 ?
O1 K1 K1 132.25(5) 5_666 3_646 ?
O1 K1 K1 47.75(5) . 3_646 ?
N2 K1 K1 130.96(5) 5_666 3_646 ?
N2 K1 K1 49.04(5) . 3_646 ?
C4 K1 K1 124.89(5) 5_666 3_646 ?
C5 K1 K1 124.58(5) 5_666 3_646 ?
N1 K1 K1 47.47(6) 5_666 3_656 ?
N1 K1 K1 132.53(5) . 3_656 ?
O1 K1 K1 47.75(5) 5_666 3_656 ?
O1 K1 K1 132.25(5) . 3_656 ?
N2 K1 K1 49.04(5) 5_666 3_656 ?
N2 K1 K1 130.96(5) . 3_656 ?
C4 K1 K1 55.11(5) 5_666 3_656 ?
C5 K1 K1 55.42(5) 5_666 3_656 ?
K1 K1 K1 180.0 3_646 3_656 ?
C10 O1 C13 108.6(4) . . ?
C10 O1 K1 121.4(2) . . ?
C13 O1 K1 109.4(2) . . ?
C10 O1 K1 121.4(2) . 3_646 ?
C13 O1 K1 109.4(2) . 3_646 ?
K1 O1 K1 84.49(9) . 3_646 ?
C5 N2 C6 120.3(4) . . ?
C5 N2 K1 98.8(2) . . ?
C6 N2 K1 124.18(19) . . ?
C5 N2 K1 98.8(2) . 3_646 ?
C6 N2 K1 124.18(19) . 3_646 ?
K1 N2 K1 81.91(10) . 3_646 ?
C1 N1 C4 104.9(4) . . ?
C1 N1 K1 130.85(17) . 3_646 ?
C4 N1 K1 99.2(2) . 3_646 ?
C1 N1 K1 130.85(17) . . ?
C4 N1 K1 99.2(2) . . ?
K1 N1 K1 85.05(11) 3_646 . ?
N2 C5 C4 124.7(4) . . ?
N2 C5 K1 58.84(19) . 3_646 ?
C4 C5 K1 76.6(2) . 3_646 ?
N2 C5 H5 124(3) . . ?
C4 C5 H5 111(3) . . ?
K1 C5 H5 145.2(4) 3_646 . ?
N2 C6 C8 116.5(5) . . ?
N2 C6 C7 106.2(3) . 7_565 ?
C8 C6 C7 110.0(3) . 7_565 ?
N2 C6 C7 106.2(3) . . ?
C8 C6 C7 110.0(3) . . ?
C7 C6 C7 107.7(5) 7_565 . ?
N1 C4 C3 110.3(5) . . ?
N1 C4 C5 124.0(4) . . ?
C3 C4 C5 125.7(5) . . ?
N1 C4 K1 56.66(18) . 3_646 ?
C3 C4 K1 139.60(18) . 3_646 ?
C5 C4 K1 78.6(2) . 3_646 ?
N1 C1 C2 112.4(5) . . ?
N1 C1 H1 123.8 . . ?
C2 C1 H1 123.8 . . ?
C2 C3 C4 106.4(5) . . ?
C2 C3 H3 126.8 . . ?
C4 C3 H3 126.8 . . ?
O1 C13 C12 107.1(5) . . ?
O1 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
O1 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C1 C2 C3 105.9(5) . . ?
C1 C2 H2 127.0 . . ?
C3 C2 H2 127.0 . . ?
C11 C12 C13 104.3(5) . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C10 O1 108.9(6) . . ?
C11 C10 H10A 109.9 . . ?
O1 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
O1 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 C12 111.0(7) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?

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
C6 N2 C5 C4 180.000(1) . . . . ?
K1 N2 C5 C4 41.55(7) . . . . ?
K1 N2 C5 C4 -41.55(7) 3_646 . . . ?
C6 N2 C5 K1 -138.45(7) . . . 3_646 ?
K1 N2 C5 K1 83.09(15) . . . 3_646 ?
C5 N2 C6 C8 0.000(1) . . . . ?
K1 N2 C6 C8 127.60(19) . . . . ?
K1 N2 C6 C8 -127.60(19) 3_646 . . . ?
C5 N2 C6 C7 -122.8(3) . . . 7_565 ?
K1 N2 C6 C7 4.8(4) . . . 7_565 ?
K1 N2 C6 C7 109.6(3) 3_646 . . 7_565 ?
C5 N2 C6 C7 122.8(3) . . . . ?
K1 N2 C6 C7 -109.6(3) . . . . ?
K1 N2 C6 C7 -4.8(4) 3_646 . . . ?
C1 N1 C4 C3 0.000(1) . . . . ?
K1 N1 C4 C3 -136.79(8) 3_646 . . . ?
K1 N1 C4 C3 136.79(8) . . . . ?
C1 N1 C4 C5 180.000(1) . . . . ?
K1 N1 C4 C5 43.21(8) 3_646 . . . ?
K1 N1 C4 C5 -43.21(8) . . . . ?
C1 N1 C4 K1 136.79(8) . . . 3_646 ?
K1 N1 C4 K1 -86.42(16) . . . 3_646 ?
N2 C5 C4 N1 0.000(1) . . . . ?
K1 C5 C4 N1 -35.69(3) 3_646 . . . ?
N2 C5 C4 C3 180.000(1) . . . . ?
K1 C5 C4 C3 144.31(3) 3_646 . . . ?
N2 C5 C4 K1 35.69(3) . . . 3_646 ?
C4 N1 C1 C2 0.000(1) . . . . ?
K1 N1 C1 C2 116.7(3) 3_646 . . . ?
K1 N1 C1 C2 -116.7(3) . . . . ?
N1 C4 C3 C2 0.000(1) . . . . ?
C5 C4 C3 C2 180.000(1) . . . . ?
K1 C4 C3 C2 -62.0(4) 3_646 . . . ?
C10 O1 C13 C12 0.000(1) . . . . ?
K1 O1 C13 C12 -134.53(11) . . . . ?
K1 O1 C13 C12 134.53(11) 3_646 . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
C4 C3 C2 C1 0.000(1) . . . . ?
O1 C13 C12 C11 0.000(1) . . . . ?
C13 O1 C10 C11 0.000(1) . . . . ?
K1 O1 C10 C11 128.1(2) . . . . ?
K1 O1 C10 C11 -128.1(2) 3_646 . . . ?
O1 C10 C11 C12 0.000(1) . . . . ?
C13 C12 C11 C10 0.000(1) . . . . ?

_refine_diff_density_max         0.936
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1566726'
_audit_update_record             
;
2017-08-04 deposited with the CCDC.	2019-04-08 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            'C18 H30 K2 N4'
_chemical_formula_weight         380.66

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   17.8883(19)
_cell_length_b                   22.588(2)
_cell_length_c                   10.5492(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4262.6(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.451
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            26666
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.877
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3776
_reflns_number_gt                2991
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1003P)²+11.8417P] 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         3776
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.2036
_refine_ls_wR_factor_gt          0.1870
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
K1 K 0.54610(4) 0.43552(4) 0.36408(8) 0.0294(3) Uani 1 1 d . . . . .
K2 K 0.75188(5) 0.48915(5) 0.45443(10) 0.0463(3) Uani 1 1 d . . . . .
N1 N 0.60076(19) 0.51677(16) 0.5342(3) 0.0338(8) Uani 1 1 d . . . . .
N2 N 0.6218(2) 0.39064(17) 0.5953(4) 0.0378(9) Uani 1 1 d . . . . .
N3 N 0.68656(19) 0.46083(19) 0.2249(3) 0.0404(9) Uani 1 1 d . . . . .
N4 N 0.6719(2) 0.58759(18) 0.0893(4) 0.0398(9) Uani 1 1 d . . . . .
C1 C 0.6175(2) 0.5749(2) 0.5494(4) 0.0367(10) Uani 1 1 d . . . . .
H1 H 0.6246 0.6020 0.4817 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6231(2) 0.5895(2) 0.6771(5) 0.0420(11) Uani 1 1 d . . . . .
H2 H 0.6451 0.6267 0.7124 0.050 Uiso 1 1 calc R U . . .
C3 C 0.6110(2) 0.5368(2) 0.7438(5) 0.0406(11) Uani 1 1 d . . . . .
H3 H 0.6119 0.5318 0.8332 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5976(2) 0.4935(2) 0.6543(4) 0.0351(10) Uani 1 1 d . . . . .
C5 C 0.5769(3) 0.4302(2) 0.6747(5) 0.0432(11) Uani 1 1 d . . . . .
H5A H 0.5844 0.4199 0.7650 0.052 Uiso 1 1 calc R U . . .
H5B H 0.5233 0.4247 0.6546 0.052 Uiso 1 1 calc R U . . .
C6 C 0.6104(3) 0.3263(2) 0.6100(5) 0.0475(12) Uani 1 1 d . . . . .
C7 C 0.6685(4) 0.2974(3) 0.5279(7) 0.0723(18) Uani 1 1 d . . . . .
H7A H 0.6601 0.3084 0.4392 0.108 Uiso 1 1 calc R U . . .
H7B H 0.6651 0.2543 0.5367 0.108 Uiso 1 1 calc R U . . .
H7C H 0.7183 0.3107 0.5542 0.108 Uiso 1 1 calc R U . . .
C8 C 0.6217(5) 0.3057(3) 0.7464(6) 0.084(2) Uani 1 1 d . . . . .
H8A H 0.6706 0.3191 0.7768 0.126 Uiso 1 1 calc R U . . .
H8B H 0.6194 0.2624 0.7499 0.126 Uiso 1 1 calc R U . . .
H8C H 0.5824 0.3225 0.8002 0.126 Uiso 1 1 calc R U . . .
C9 C 0.5339(4) 0.3087(3) 0.5649(10) 0.108(3) Uani 1 1 d . . . . .
H9A H 0.4960 0.3278 0.6179 0.161 Uiso 1 1 calc R U . . .
H9B H 0.5285 0.2656 0.5708 0.161 Uiso 1 1 calc R U . . .
H9C H 0.5274 0.3211 0.4766 0.161 Uiso 1 1 calc R U . . .
C10 C 0.6807(3) 0.4034(2) 0.1882(5) 0.0504(13) Uani 1 1 d . . . . .
H10 H 0.7114 0.3724 0.2199 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6256(3) 0.3954(2) 0.1007(5) 0.0526(14) Uani 1 1 d . . . . .
H11 H 0.6114 0.3593 0.0613 0.063 Uiso 1 1 calc R U . . .
C12 C 0.5947(3) 0.4504(3) 0.0812(4) 0.0474(13) Uani 1 1 d . . . . .
H12 H 0.5548 0.4596 0.0252 0.057 Uiso 1 1 calc R U . . .
C13 C 0.6324(2) 0.48960(19) 0.1581(4) 0.0348(10) Uani 1 1 d . . . . .
C14 C 0.6189(4) 0.5536(2) 0.1667(6) 0.071(2) Uani 1 1 d . . . . .
H14A H 0.6233 0.5662 0.2562 0.086 Uiso 1 1 calc R U . . .
H14B H 0.5674 0.5622 0.1381 0.086 Uiso 1 1 calc R U . . .
C15 C 0.6536(3) 0.6505(2) 0.0710(5) 0.0406(11) Uani 1 1 d . . . . .
C16 C 0.5771(3) 0.6559(3) 0.0098(6) 0.0594(15) Uani 1 1 d . . . . .
H16A H 0.5734 0.6279 -0.0609 0.089 Uiso 1 1 calc R U . . .
H16B H 0.5702 0.6963 -0.0219 0.089 Uiso 1 1 calc R U . . .
H16C H 0.5384 0.6469 0.0726 0.089 Uiso 1 1 calc R U . . .
C17 C 0.7105(3) 0.6735(3) -0.0251(6) 0.0628(15) Uani 1 1 d . . . . .
H17A H 0.7605 0.6731 0.0129 0.094 Uiso 1 1 calc R U . . .
H17B H 0.6975 0.7140 -0.0495 0.094 Uiso 1 1 calc R U . . .
H17C H 0.7101 0.6481 -0.1004 0.094 Uiso 1 1 calc R U . . .
C18 C 0.6573(4) 0.6866(3) 0.1916(6) 0.0734(19) Uani 1 1 d . . . . .
H18A H 0.6234 0.6696 0.2548 0.110 Uiso 1 1 calc R U . . .
H18B H 0.6423 0.7275 0.1736 0.110 Uiso 1 1 calc R U . . .
H18C H 0.7085 0.6862 0.2245 0.110 Uiso 1 1 calc R U . . .
H4A H 0.711(2) 0.5891(17) 0.116(4) 0.009(10) Uiso 1 1 d . . . . .
H2A H 0.672(3) 0.400(2) 0.617(5) 0.053(15) 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
K1 N1 2.747(4) . ?
K1 C13 2.932(4) . ?
K1 N3 2.965(3) . ?
K1 N1 3.035(4) 5_666 ?
K1 C4 3.036(4) 5_666 ?
K1 C1 3.075(4) 5_666 ?
K1 C3 3.096(4) 5_666 ?
K1 C2 3.110(4) 5_666 ?
K1 C10 3.125(4) . ?
K1 C12 3.126(5) . ?
K1 C11 3.250(5) . ?
K1 C4 3.456(4) . ?
K2 N3 2.763(4) . ?
K2 N1 2.899(4) . ?
K2 N4 2.971(4) 8_756 ?
K2 C13 2.984(4) 8_756 ?
K2 N3 3.125(4) 8_756 ?
K2 C12 3.176(5) 8_756 ?
K2 C1 3.245(4) . ?
K2 C10 3.361(5) 8_756 ?
K2 C11 3.417(5) 8_756 ?
K2 C4 3.474(4) . ?
K2 C3 3.480(5) 8_755 ?
K2 C14 3.531(5) 8_756 ?
K2 H2A 3.02(5) . ?
N1 C1 1.356(6) . ?
N1 C4 1.373(5) . ?
N1 K1 3.036(4) 5_666 ?
N2 C5 1.465(6) . ?
N2 C6 1.476(6) . ?
N2 H2A 0.94(6) . ?
N3 C10 1.359(7) . ?
N3 C13 1.363(6) . ?
N3 K2 3.125(4) 8_755 ?
N4 C14 1.468(7) . ?
N4 C15 1.471(6) . ?
N4 K2 2.971(4) 8_755 ?
N4 H4A 0.76(4) . ?
C1 C2 1.391(6) . ?
C1 K1 3.075(4) 5_666 ?
C1 H1 0.9500 . ?
C2 C3 1.400(7) . ?
C2 K1 3.110(4) 5_666 ?
C2 H2 1.0000 . ?
C3 C4 1.380(6) . ?
C3 K1 3.096(4) 5_666 ?
C3 K2 3.480(5) 8_756 ?
C3 H3 0.9500 . ?
C4 C5 1.493(6) . ?
C4 K1 3.037(4) 5_666 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C9 1.502(8) . ?
C6 C7 1.503(8) . ?
C6 C8 1.526(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.362(8) . ?
C10 K2 3.361(5) 8_755 ?
C10 H10 0.9500 . ?
C11 C12 1.375(8) . ?
C11 K2 3.417(5) 8_755 ?
C11 H11 0.9500 . ?
C12 C13 1.378(7) . ?
C12 K2 3.176(5) 8_755 ?
C12 H12 0.9500 . ?
C13 C14 1.467(7) . ?
C13 K2 2.984(4) 8_755 ?
C14 K2 3.531(5) 8_755 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C18 1.512(7) . ?
C15 C16 1.518(7) . ?
C15 C17 1.528(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 K1 C13 91.06(12) . . ?
N1 K1 N3 83.86(11) . . ?
C13 K1 N3 26.73(12) . . ?
N1 K1 N1 80.79(11) . 5_666 ?
C13 K1 N1 124.72(11) . 5_666 ?
N3 K1 N1 147.12(11) . 5_666 ?
N1 K1 C4 89.45(12) . 5_666 ?
C13 K1 C4 100.28(12) . 5_666 ?
N3 K1 C4 125.74(12) . 5_666 ?
N1 K1 C4 26.13(10) 5_666 5_666 ?
N1 K1 C1 101.30(11) . 5_666 ?
C13 K1 C1 138.83(13) . 5_666 ?
N3 K1 C1 165.49(12) . 5_666 ?
N1 K1 C1 25.63(11) 5_666 5_666 ?
C4 K1 C1 41.68(12) 5_666 5_666 ?
N1 K1 C3 115.36(12) . 5_666 ?
C13 K1 C3 96.97(13) . 5_666 ?
N3 K1 C3 123.25(12) . 5_666 ?
N1 K1 C3 43.32(11) 5_666 5_666 ?
C4 K1 C3 25.98(12) 5_666 5_666 ?
C1 K1 C3 42.29(13) 5_666 5_666 ?
N1 K1 C2 124.01(11) . 5_666 ?
C13 K1 C2 118.99(14) . 5_666 ?
N3 K1 C2 142.24(12) . 5_666 ?
N1 K1 C2 43.25(11) 5_666 5_666 ?
C4 K1 C2 42.52(13) 5_666 5_666 ?
C1 K1 C2 25.98(12) 5_666 5_666 ?
C3 K1 C2 26.08(13) 5_666 5_666 ?
N1 K1 C10 105.61(13) . . ?
C13 K1 C10 41.52(13) . . ?
N3 K1 C10 25.61(13) . . ?
N1 K1 C10 163.56(12) 5_666 . ?
C4 K1 C10 137.49(13) 5_666 . ?
C1 K1 C10 153.09(14) 5_666 . ?
C3 K1 C10 121.88(14) 5_666 . ?
C2 K1 C10 128.65(14) 5_666 . ?
N1 K1 C12 116.95(12) . . ?
C13 K1 C12 26.04(13) . . ?
N3 K1 C12 43.22(11) . . ?
N1 K1 C12 122.68(12) 5_666 . ?
C4 K1 C12 96.76(13) 5_666 . ?
C1 K1 C12 123.78(12) 5_666 . ?
C3 K1 C12 83.10(13) 5_666 . ?
C2 K1 C12 99.02(13) 5_666 . ?
C10 K1 C12 40.89(14) . . ?
N1 K1 C11 126.11(12) . . ?
C13 K1 C11 41.62(13) . . ?
N3 K1 C11 42.27(12) . . ?
N1 K1 C11 141.24(13) 5_666 . ?
C4 K1 C11 117.59(14) 5_666 . ?
C1 K1 C11 130.45(13) 5_666 . ?
C3 K1 C11 98.01(14) 5_666 . ?
C2 K1 C11 104.80(13) 5_666 . ?
C10 K1 C11 24.58(14) . . ?
C12 K1 C11 24.80(14) . . ?
N1 K1 C4 22.00(11) . . ?
C13 K1 C4 111.00(12) . . ?
N3 K1 C4 98.02(10) . . ?
N1 K1 C4 77.48(9) 5_666 . ?
C4 K1 C4 94.73(11) 5_666 . ?
C1 K1 C4 91.15(11) 5_666 . ?
C3 K1 C4 119.43(11) 5_666 . ?
C2 K1 C4 116.91(11) 5_666 . ?
C10 K1 C4 114.12(13) . . ?
C12 K1 C4 136.97(12) . . ?
C11 K1 C4 138.29(12) . . ?
N3 K2 N1 84.83(10) . . ?
N3 K2 N4 141.89(12) . 8_756 ?
N1 K2 N4 97.33(12) . 8_756 ?
N3 K2 C13 157.68(13) . 8_756 ?
N1 K2 C13 115.92(11) . 8_756 ?
N4 K2 C13 48.26(12) 8_756 8_756 ?
N3 K2 N3 154.38(17) . 8_756 ?
N1 K2 N3 96.17(10) . 8_756 ?
N4 K2 N3 63.53(11) 8_756 8_756 ?
C13 K2 N3 25.66(11) 8_756 8_756 ?
N3 K2 C12 132.10(13) . 8_756 ?
N1 K2 C12 137.97(11) . 8_756 ?
N4 K2 C12 66.95(13) 8_756 8_756 ?
C13 K2 C12 25.60(13) 8_756 8_756 ?
N3 K2 C12 41.80(11) 8_756 8_756 ?
N3 K2 C1 95.49(11) . . ?
N1 K2 C1 24.68(10) . . ?
N4 K2 C1 75.24(12) 8_756 . ?
C13 K2 C1 106.82(12) 8_756 . ?
N3 K2 C1 95.80(11) 8_756 . ?
C12 K2 C1 132.42(12) 8_756 . ?
N3 K2 C10 131.40(14) . 8_756 ?
N1 K2 C10 104.23(12) . 8_756 ?
N4 K2 C10 85.15(12) 8_756 8_756 ?
C13 K2 C10 39.14(12) 8_756 8_756 ?
N3 K2 C10 23.83(12) 8_756 8_756 ?
C12 K2 C10 38.89(13) 8_756 8_756 ?
C1 K2 C10 112.54(13) . 8_756 ?
N3 K2 C11 121.57(13) . 8_756 ?
N1 K2 C11 126.90(13) . 8_756 ?
N4 K2 C11 87.33(12) 8_756 8_756 ?
C13 K2 C11 39.80(12) 8_756 8_756 ?
N3 K2 C11 40.05(11) 8_756 8_756 ?
C12 K2 C11 23.71(14) 8_756 8_756 ?
C1 K2 C11 134.87(13) . 8_756 ?
C10 K2 C11 23.17(13) 8_756 8_756 ?
N3 K2 C4 101.69(10) . . ?
N1 K2 C4 22.66(10) . . ?
N4 K2 C4 93.01(12) 8_756 . ?
C13 K2 C4 96.54(12) 8_756 . ?
N3 K2 C4 74.41(10) 8_756 . ?
C12 K2 C4 116.00(12) 8_756 . ?
C1 K2 C4 37.57(11) . . ?
C10 K2 C4 81.72(12) 8_756 . ?
C11 K2 C4 104.65(13) 8_756 . ?
N3 K2 C3 79.05(11) . 8_755 ?
N1 K2 C3 140.89(12) . 8_755 ?
N4 K2 C3 75.59(12) 8_756 8_755 ?
C13 K2 C3 88.27(12) 8_756 8_755 ?
N3 K2 C3 113.46(11) 8_756 8_755 ?
C12 K2 C3 75.24(12) 8_756 8_755 ?
C1 K2 C3 122.33(12) . 8_755 ?
C10 K2 C3 113.20(13) 8_756 8_755 ?
C11 K2 C3 91.60(14) 8_756 8_755 ?
C4 K2 C3 159.81(12) . 8_755 ?
N3 K2 C14 158.06(15) . 8_756 ?
N1 K2 C14 109.72(15) . 8_756 ?
N4 K2 C14 24.18(12) 8_756 8_756 ?
C13 K2 C14 24.21(12) 8_756 8_756 ?
N3 K2 C14 43.51(13) 8_756 8_756 ?
C12 K2 C14 44.05(14) 8_756 8_756 ?
C1 K2 C14 92.46(14) . 8_756 ?
C10 K2 C14 62.44(12) 8_756 8_756 ?
C11 K2 C14 63.20(13) 8_756 8_756 ?
C4 K2 C14 97.07(15) . 8_756 ?
C3 K2 C14 79.42(15) 8_755 8_756 ?
N3 K2 H2A 98.2(11) . . ?
N1 K2 H2A 62.3(10) . . ?
N4 K2 H2A 116.5(10) 8_756 . ?
C13 K2 H2A 85.5(11) 8_756 . ?
N3 K2 H2A 60.7(11) 8_756 . ?
C12 K2 H2A 89.2(11) 8_756 . ?
C1 K2 H2A 82.6(10) . . ?
C10 K2 H2A 50.7(11) 8_756 . ?
C11 K2 H2A 68.4(11) 8_756 . ?
C4 K2 H2A 45.2(10) . . ?
C3 K2 H2A 155.0(10) 8_755 . ?
C14 K2 H2A 103.1(11) 8_756 . ?
C1 N1 C4 105.7(4) . . ?
C1 N1 K1 143.4(3) . . ?
C4 N1 K1 109.4(3) . . ?
C1 N1 K2 92.1(2) . . ?
C4 N1 K2 102.9(3) . . ?
K1 N1 K2 89.91(10) . . ?
C1 N1 K1 78.8(2) . 5_666 ?
C4 N1 K1 77.0(2) . 5_666 ?
K1 N1 K1 99.21(11) . 5_666 ?
K2 N1 K1 170.40(14) . 5_666 ?
C5 N2 C6 117.7(4) . . ?
C5 N2 H2A 104(3) . . ?
C6 N2 H2A 109(3) . . ?
C10 N3 C13 104.7(4) . . ?
C10 N3 K2 120.2(3) . . ?
C13 N3 K2 130.0(3) . . ?
C10 N3 K1 83.8(2) . . ?
C13 N3 K1 75.3(2) . . ?
K2 N3 K1 88.24(10) . . ?
C10 N3 K2 87.9(3) . 8_755 ?
C13 N3 K2 71.4(2) . 8_755 ?
K2 N3 K2 127.13(12) . 8_755 ?
K1 N3 K2 142.19(13) . 8_755 ?
C14 N4 C15 115.8(4) . . ?
C14 N4 K2 99.8(3) . 8_755 ?
C15 N4 K2 139.7(3) . 8_755 ?
C14 N4 H4A 114(3) . . ?
C15 N4 H4A 102(3) . . ?
K2 N4 H4A 78(3) 8_755 . ?
N1 C1 C2 111.2(4) . . ?
N1 C1 K1 75.6(2) . 5_666 ?
C2 C1 K1 78.4(3) . 5_666 ?
N1 C1 K2 63.2(2) . . ?
C2 C1 K2 112.9(3) . . ?
K1 C1 K2 138.69(16) 5_666 . ?
N1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
K1 C1 H1 113.5 5_666 . ?
K2 C1 H1 93.1 . . ?
C1 C2 C3 105.8(4) . . ?
C1 C2 K1 75.6(3) . 5_666 ?
C3 C2 K1 76.4(2) . 5_666 ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
K1 C2 H2 126.1 5_666 . ?
C4 C3 C2 106.6(4) . . ?
C4 C3 K1 74.6(2) . 5_666 ?
C2 C3 K1 77.5(3) . 5_666 ?
C4 C3 K2 109.9(3) . 8_756 ?
C2 C3 K2 118.4(3) . 8_756 ?
K1 C3 K2 159.54(17) 5_666 8_756 ?
C4 C3 H3 126.7 . . ?
C2 C3 H3 126.7 . . ?
K1 C3 H3 113.8 5_666 . ?
K2 C3 H3 47.0 8_756 . ?
N1 C4 C3 110.7(4) . . ?
N1 C4 C5 120.7(4) . . ?
C3 C4 C5 128.5(4) . . ?
N1 C4 K1 76.9(2) . 5_666 ?
C3 C4 K1 79.4(2) . 5_666 ?
C5 C4 K1 107.7(3) . 5_666 ?
N1 C4 K1 48.6(2) . . ?
C3 C4 K1 157.1(3) . . ?
C5 C4 K1 72.4(2) . . ?
K1 C4 K1 85.27(11) 5_666 . ?
N1 C4 K2 54.4(2) . . ?
C3 C4 K2 107.3(3) . . ?
C5 C4 K2 105.0(3) . . ?
K1 C4 K2 130.44(14) 5_666 . ?
K1 C4 K2 70.32(8) . . ?
N2 C5 C4 111.4(4) . . ?
N2 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N2 C6 C9 110.7(4) . . ?
N2 C6 C7 105.8(4) . . ?
C9 C6 C7 109.5(6) . . ?
N2 C6 C8 112.3(5) . . ?
C9 C6 C8 109.8(6) . . ?
C7 C6 C8 108.6(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C11 112.1(5) . . ?
N3 C10 K1 70.6(2) . . ?
C11 C10 K1 82.9(3) . . ?
N3 C10 K2 68.3(2) . 8_755 ?
C11 C10 K2 80.7(3) . 8_755 ?
K1 C10 K2 125.33(16) . 8_755 ?
N3 C10 H10 124.0 . . ?
C11 C10 H10 124.0 . . ?
K1 C10 H10 114.1 . . ?
K2 C10 H10 118.4 8_755 . ?
C10 C11 C12 105.8(5) . . ?
C10 C11 K1 72.6(3) . . ?
C12 C11 K1 72.6(3) . . ?
C10 C11 K2 76.1(3) . 8_755 ?
C12 C11 K2 68.3(3) . 8_755 ?
K1 C11 K2 119.60(16) . 8_755 ?
C10 C11 H11 127.1 . . ?
C12 C11 H11 127.1 . . ?
K1 C11 H11 119.8 . . ?
K2 C11 H11 120.4 8_755 . ?
C13 C12 C11 107.2(4) . . ?
C13 C12 K1 69.1(2) . . ?
C11 C12 K1 82.6(3) . . ?
C13 C12 K2 69.4(2) . 8_755 ?
C11 C12 K2 88.0(3) . 8_755 ?
K1 C12 K2 132.20(16) . 8_755 ?
C13 C12 H12 126.4 . . ?
C11 C12 H12 126.4 . . ?
K1 C12 H12 114.1 . . ?
K2 C12 H12 109.1 8_755 . ?
N3 C13 C12 110.2(4) . . ?
N3 C13 C14 123.7(5) . . ?
C12 C13 C14 126.1(5) . . ?
N3 C13 K1 78.0(2) . . ?
C12 C13 K1 84.9(3) . . ?
C14 C13 K1 106.2(3) . . ?
N3 C13 K2 83.0(2) . 8_755 ?
C12 C13 K2 85.0(3) . 8_755 ?
C14 C13 K2 99.3(3) . 8_755 ?
K1 C13 K2 153.83(17) . 8_755 ?
C13 C14 N4 112.1(4) . . ?
C13 C14 K2 56.5(2) . 8_755 ?
N4 C14 K2 56.0(2) . 8_755 ?
C13 C14 H14A 109.2 . . ?
N4 C14 H14A 109.2 . . ?
K2 C14 H14A 132.2 8_755 . ?
C13 C14 H14B 109.2 . . ?
N4 C14 H14B 109.2 . . ?
K2 C14 H14B 119.9 8_755 . ?
H14A C14 H14B 107.9 . . ?
N4 C15 C18 113.7(4) . . ?
N4 C15 C16 109.5(4) . . ?
C18 C15 C16 110.7(5) . . ?
N4 C15 C17 105.5(4) . . ?
C18 C15 C17 110.2(5) . . ?
C16 C15 C17 106.9(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C4 N1 C1 C2 -1.7(5) . . . . ?
K1 N1 C1 C2 161.6(3) . . . . ?
K2 N1 C1 C2 -105.7(3) . . . . ?
K1 N1 C1 C2 71.2(3) 5_666 . . . ?
C4 N1 C1 K1 -72.9(3) . . . 5_666 ?
K1 N1 C1 K1 90.4(4) . . . 5_666 ?
K2 N1 C1 K1 -176.92(12) . . . 5_666 ?
C4 N1 C1 K2 104.0(3) . . . . ?
K1 N1 C1 K2 -92.6(4) . . . . ?
K1 N1 C1 K2 176.92(12) 5_666 . . . ?
N1 C1 C2 C3 1.7(5) . . . . ?
K1 C1 C2 C3 71.1(3) 5_666 . . . ?
K2 C1 C2 C3 -67.1(4) . . . . ?
N1 C1 C2 K1 -69.4(3) . . . 5_666 ?
K2 C1 C2 K1 -138.2(2) . . . 5_666 ?
C1 C2 C3 C4 -1.0(5) . . . . ?
K1 C2 C3 C4 69.5(3) 5_666 . . . ?
C1 C2 C3 K1 -70.5(3) . . . 5_666 ?
C1 C2 C3 K2 123.4(3) . . . 8_756 ?
K1 C2 C3 K2 -166.1(2) 5_666 . . 8_756 ?
C1 N1 C4 C3 1.0(5) . . . . ?
K1 N1 C4 C3 -168.5(3) . . . . ?
K2 N1 C4 C3 97.0(3) . . . . ?
K1 N1 C4 C3 -73.2(3) 5_666 . . . ?
C1 N1 C4 C5 177.2(4) . . . . ?
K1 N1 C4 C5 7.7(5) . . . . ?
K2 N1 C4 C5 -86.9(4) . . . . ?
K1 N1 C4 C5 103.0(4) 5_666 . . . ?
C1 N1 C4 K1 74.2(3) . . . 5_666 ?
K1 N1 C4 K1 -95.31(16) . . . 5_666 ?
K2 N1 C4 K1 170.15(14) . . . 5_666 ?
C1 N1 C4 K1 169.5(4) . . . . ?
K2 N1 C4 K1 -94.54(19) . . . . ?
K1 N1 C4 K1 95.31(16) 5_666 . . . ?
C1 N1 C4 K2 -95.9(3) . . . . ?
K1 N1 C4 K2 94.54(19) . . . . ?
K1 N1 C4 K2 -170.15(14) 5_666 . . . ?
C2 C3 C4 N1 0.0(5) . . . . ?
K1 C3 C4 N1 71.5(3) 5_666 . . . ?
K2 C3 C4 N1 -129.5(3) 8_756 . . . ?
C2 C3 C4 C5 -175.8(4) . . . . ?
K1 C3 C4 C5 -104.3(4) 5_666 . . . ?
K2 C3 C4 C5 54.8(5) 8_756 . . . ?
C2 C3 C4 K1 -71.5(3) . . . 5_666 ?
K2 C3 C4 K1 159.0(2) 8_756 . . 5_666 ?
C2 C3 C4 K1 -22.5(9) . . . . ?
K1 C3 C4 K1 49.0(7) 5_666 . . . ?
K2 C3 C4 K1 -152.0(6) 8_756 . . . ?
C2 C3 C4 K2 57.7(4) . . . . ?
K1 C3 C4 K2 129.27(18) 5_666 . . . ?
K2 C3 C4 K2 -71.7(3) 8_756 . . . ?
C6 N2 C5 C4 176.8(4) . . . . ?
N1 C4 C5 N2 51.1(6) . . . . ?
C3 C4 C5 N2 -133.5(5) . . . . ?
K1 C4 C5 N2 136.1(3) 5_666 . . . ?
K1 C4 C5 N2 57.1(3) . . . . ?
K2 C4 C5 N2 -6.1(4) . . . . ?
C5 N2 C6 C9 67.2(7) . . . . ?
C5 N2 C6 C7 -174.4(4) . . . . ?
C5 N2 C6 C8 -56.0(6) . . . . ?
C13 N3 C10 C11 0.5(5) . . . . ?
K2 N3 C10 C11 157.7(3) . . . . ?
K1 N3 C10 C11 73.5(4) . . . . ?
K2 N3 C10 C11 -69.6(4) 8_755 . . . ?
C13 N3 C10 K1 -72.9(3) . . . . ?
K2 N3 C10 K1 84.3(2) . . . . ?
K2 N3 C10 K1 -143.07(12) 8_755 . . . ?
C13 N3 C10 K2 70.1(3) . . . 8_755 ?
K2 N3 C10 K2 -132.7(2) . . . 8_755 ?
K1 N3 C10 K2 143.07(12) . . . 8_755 ?
N3 C10 C11 C12 -0.3(6) . . . . ?
K1 C10 C11 C12 65.4(3) . . . . ?
K2 C10 C11 C12 -62.2(3) 8_755 . . . ?
N3 C10 C11 K1 -65.7(3) . . . . ?
K2 C10 C11 K1 -127.66(13) 8_755 . . . ?
N3 C10 C11 K2 61.9(3) . . . 8_755 ?
K1 C10 C11 K2 127.66(13) . . . 8_755 ?
C10 C11 C12 C13 -0.1(5) . . . . ?
K1 C11 C12 C13 65.4(3) . . . . ?
K2 C11 C12 C13 -67.7(3) 8_755 . . . ?
C10 C11 C12 K1 -65.4(3) . . . . ?
K2 C11 C12 K1 -133.02(14) 8_755 . . . ?
C10 C11 C12 K2 67.6(4) . . . 8_755 ?
K1 C11 C12 K2 133.02(14) . . . 8_755 ?
C10 N3 C13 C12 -0.6(5) . . . . ?
K2 N3 C13 C12 -154.7(3) . . . . ?
K1 N3 C13 C12 -79.9(3) . . . . ?
K2 N3 C13 C12 82.0(3) 8_755 . . . ?
C10 N3 C13 C14 -179.1(4) . . . . ?
K2 N3 C13 C14 26.8(6) . . . . ?
K1 N3 C13 C14 101.6(4) . . . . ?
K2 N3 C13 C14 -96.5(4) 8_755 . . . ?
C10 N3 C13 K1 79.3(3) . . . . ?
K2 N3 C13 K1 -74.8(3) . . . . ?
K2 N3 C13 K1 161.93(13) 8_755 . . . ?
C10 N3 C13 K2 -82.6(3) . . . 8_755 ?
K2 N3 C13 K2 123.3(3) . . . 8_755 ?
K1 N3 C13 K2 -161.93(13) . . . 8_755 ?
C11 C12 C13 N3 0.4(5) . . . . ?
K1 C12 C13 N3 75.2(3) . . . . ?
K2 C12 C13 N3 -80.6(3) 8_755 . . . ?
C11 C12 C13 C14 178.9(4) . . . . ?
K1 C12 C13 C14 -106.3(4) . . . . ?
K2 C12 C13 C14 97.9(4) 8_755 . . . ?
C11 C12 C13 K1 -74.8(3) . . . . ?
K2 C12 C13 K1 -155.83(15) 8_755 . . . ?
C11 C12 C13 K2 81.0(3) . . . 8_755 ?
K1 C12 C13 K2 155.83(15) . . . 8_755 ?
N3 C13 C14 N4 80.3(7) . . . . ?
C12 C13 C14 N4 -98.0(7) . . . . ?
K1 C13 C14 N4 166.5(4) . . . . ?
K2 C13 C14 N4 -7.4(6) 8_755 . . . ?
N3 C13 C14 K2 87.7(4) . . . 8_755 ?
C12 C13 C14 K2 -90.6(4) . . . 8_755 ?
K1 C13 C14 K2 173.9(3) . . . 8_755 ?
C15 N4 C14 C13 168.0(5) . . . . ?
K2 N4 C14 C13 7.4(6) 8_755 . . . ?
C15 N4 C14 K2 160.5(5) . . . 8_755 ?
C14 N4 C15 C18 66.3(6) . . . . ?
K2 N4 C15 C18 -144.2(5) 8_755 . . . ?
C14 N4 C15 C16 -58.1(6) . . . . ?
K2 N4 C15 C16 91.4(5) 8_755 . . . ?
C14 N4 C15 C17 -172.8(5) . . . . ?
K2 N4 C15 C17 -23.3(6) 8_755 . . . ?

_refine_diff_density_max         0.667
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.070

