# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_sb1355_hy_compound_9d
_database_code_depnum_ccdc_archive 'CCDC 2152372'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2022-02-16 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
N-(adamantan-1-yl)pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5-amine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N4'
_chemical_formula_sum            'C24 H24 N4'
_chemical_formula_weight         368.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.5540(6)
_cell_length_b                   12.6859(12)
_cell_length_c                   23.2169(21)
_cell_angle_alpha                90
_cell_angle_beta                 97.357(4)
_cell_angle_gamma                90
_cell_volume                     1914.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      72.1

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.599
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8312
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 0.5 deg., 9+1 runs, 3139 frames, 20/25/30 sec./frame
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26584
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.839
_diffrn_reflns_theta_max         72.117
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3764
_reflns_number_gt                3445
_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       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0382P)²+0.5418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.40220(16) 0.61812(8) 0.67366(4) 0.0393(2) Uani 1 1 d . . . . .
C2 C 0.50358(18) 0.55543(9) 0.71469(5) 0.0372(3) Uani 1 1 d . . . . .
N3 N 0.67914(15) 0.49881(8) 0.70802(4) 0.0377(2) Uani 1 1 d . . . . .
C4 C 0.7916(2) 0.49274(10) 0.66219(5) 0.0432(3) Uani 1 1 d . . . . .
H4 H 0.7497 0.5288 0.6278 0.052 Uiso 1 1 calc R U . . .
C5 C 0.9635(2) 0.43364(11) 0.66782(6) 0.0474(3) Uani 1 1 d . . . . .
H5 H 1.0422 0.4292 0.6373 0.057 Uiso 1 1 calc R U . . .
C6 C 1.0246(2) 0.37836(11) 0.71993(6) 0.0511(3) Uani 1 1 d . . . . .
H6 H 1.1430 0.3373 0.7232 0.061 Uiso 1 1 calc R U . . .
C7 C 0.9142(2) 0.38390(11) 0.76527(6) 0.0486(3) Uani 1 1 d . . . . .
H7 H 0.9563 0.3465 0.7992 0.058 Uiso 1 1 calc R U . . .
C8 C 0.73488(19) 0.44665(10) 0.76101(5) 0.0404(3) Uani 1 1 d . . . . .
N9 N 0.60476(17) 0.46640(9) 0.79921(4) 0.0448(3) Uani 1 1 d . . . . .
C10 C 0.46423(18) 0.53500(9) 0.77044(5) 0.0380(3) Uani 1 1 d . . . . .
C11 C 0.28958(18) 0.58741(9) 0.78863(5) 0.0382(3) Uani 1 1 d . . . . .
C12 C 0.2324(2) 0.57744(11) 0.84458(5) 0.0479(3) Uani 1 1 d . . . . .
H12 H 0.3124 0.5371 0.8723 0.058 Uiso 1 1 calc R U . . .
C13 C 0.0594(2) 0.62672(13) 0.85870(6) 0.0561(4) Uani 1 1 d . . . . .
H13 H 0.0229 0.6201 0.8959 0.067 Uiso 1 1 calc R U . . .
C14 C -0.0618(2) 0.68679(12) 0.81715(6) 0.0526(3) Uani 1 1 d . . . . .
H14 H -0.1804 0.7192 0.8266 0.063 Uiso 1 1 calc R U . . .
C15 C -0.0070(2) 0.69833(10) 0.76246(6) 0.0441(3) Uani 1 1 d . . . . .
H15 H -0.0896 0.7383 0.7352 0.053 Uiso 1 1 calc R U . . .
C16 C 0.17167(18) 0.65092(9) 0.74687(5) 0.0367(3) Uani 1 1 d . . . . .
C17 C 0.23776(18) 0.66481(9) 0.68918(5) 0.0368(3) Uani 1 1 d . . . . .
N18 N 0.12442(17) 0.72881(9) 0.64991(4) 0.0443(3) Uani 1 1 d . . . . .
H18 H 0.041(2) 0.7757(13) 0.6635(6) 0.053 Uiso 1 1 d . U . . .
C19 C 0.14807(18) 0.73993(10) 0.58797(5) 0.0372(3) Uani 1 1 d . . . . .
C20 C 0.1288(2) 0.63297(10) 0.55689(5) 0.0437(3) Uani 1 1 d . . . . .
H20A H -0.0011 0.6003 0.5624 0.052 Uiso 1 1 calc R U . . .
H20B H 0.2391 0.5868 0.5733 0.052 Uiso 1 1 calc R U . . .
C21 C 0.1401(2) 0.64842(11) 0.49169(6) 0.0509(3) Uani 1 1 d . . . . .
H21 H 0.1292 0.5797 0.4722 0.061 Uiso 1 1 calc R U . . .
C22 C 0.3450(2) 0.69909(13) 0.48344(6) 0.0558(4) Uani 1 1 d . . . . .
H22A H 0.3549 0.7071 0.4423 0.067 Uiso 1 1 calc R U . . .
H22B H 0.4573 0.6544 0.5002 0.067 Uiso 1 1 calc R U . . .
C23 C 0.3608(2) 0.80676(12) 0.51296(6) 0.0511(3) Uani 1 1 d . . . . .
H23 H 0.4919 0.8398 0.5072 0.061 Uiso 1 1 calc R U . . .
C24 C 0.1839(2) 0.87706(12) 0.48706(6) 0.0553(4) Uani 1 1 d . . . . .
H24A H 0.1899 0.8869 0.4459 0.066 Uiso 1 1 calc R U . . .
H24B H 0.1949 0.9456 0.5057 0.066 Uiso 1 1 calc R U . . .
C25 C -0.0202(2) 0.82550(11) 0.49618(6) 0.0487(3) Uani 1 1 d . . . . .
H25 H -0.1343 0.8707 0.4797 0.058 Uiso 1 1 calc R U . . .
C26 C -0.0300(2) 0.80995(11) 0.56108(5) 0.0446(3) Uani 1 1 d . . . . .
H26A H -0.1600 0.7774 0.5666 0.054 Uiso 1 1 calc R U . . .
H26B H -0.0224 0.8779 0.5804 0.054 Uiso 1 1 calc R U . . .
C27 C -0.0363(2) 0.71870(12) 0.46559(6) 0.0556(4) Uani 1 1 d . . . . .
H27A H -0.1668 0.6858 0.4702 0.067 Uiso 1 1 calc R U . . .
H27B H -0.0300 0.7282 0.4244 0.067 Uiso 1 1 calc R U . . .
C28 C 0.35138(19) 0.79255(10) 0.57826(5) 0.0430(3) Uani 1 1 d . . . . .
H28A H 0.4658 0.7493 0.5951 0.052 Uiso 1 1 calc R U . . .
H28B H 0.3624 0.8607 0.5974 0.052 Uiso 1 1 calc R U . . .


_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
N1 C17 1.3197(15) . ?
N1 C2 1.3488(15) . ?
C2 C10 1.3764(16) . ?
C2 N3 1.3819(15) . ?
N3 C4 1.3717(16) . ?
N3 C8 1.4035(15) . ?
C4 C5 1.3458(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.353(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.4123(18) . ?
C7 H7 0.9300 . ?
C8 N9 1.3305(17) . ?
N9 C10 1.3764(16) . ?
C10 C11 1.4333(17) . ?
C11 C12 1.4031(17) . ?
C11 C16 1.4122(17) . ?
C12 C13 1.371(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.3709(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.4042(17) . ?
C15 H15 0.9300 . ?
C16 C17 1.4702(16) . ?
C17 N18 1.3671(15) . ?
N18 C19 1.4726(15) . ?
N18 H18 0.891(16) . ?
C19 C28 1.5326(17) . ?
C19 C20 1.5344(17) . ?
C19 C26 1.5346(16) . ?
C20 C21 1.5375(18) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C27 1.523(2) . ?
C21 C22 1.523(2) . ?
C21 H21 0.9800 . ?
C22 C23 1.526(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.524(2) . ?
C23 C28 1.5359(18) . ?
C23 H23 0.9800 . ?
C24 C25 1.528(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C27 1.527(2) . ?
C25 C26 1.5290(18) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?

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
C17 N1 C2 114.67(10) . . ?
N1 C2 C10 129.83(11) . . ?
N1 C2 N3 124.70(11) . . ?
C10 C2 N3 105.46(10) . . ?
C4 N3 C2 130.83(10) . . ?
C4 N3 C8 123.24(10) . . ?
C2 N3 C8 105.89(10) . . ?
C5 C4 N3 118.83(12) . . ?
C5 C4 H4 120.6 . . ?
N3 C4 H4 120.6 . . ?
C4 C5 C6 120.13(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 121.32(12) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.85(12) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
N9 C8 N3 112.24(11) . . ?
N9 C8 C7 131.15(12) . . ?
N3 C8 C7 116.61(11) . . ?
C8 N9 C10 103.99(10) . . ?
N9 C10 C2 112.40(11) . . ?
N9 C10 C11 131.33(11) . . ?
C2 C10 C11 116.27(11) . . ?
C12 C11 C16 119.96(12) . . ?
C12 C11 C10 123.31(12) . . ?
C16 C11 C10 116.73(11) . . ?
C13 C12 C11 120.50(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.93(12) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.34(13) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 121.27(13) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 117.93(11) . . ?
C15 C16 C17 122.42(11) . . ?
C11 C16 C17 119.65(11) . . ?
N1 C17 N18 118.51(10) . . ?
N1 C17 C16 122.77(11) . . ?
N18 C17 C16 118.72(11) . . ?
C17 N18 C19 126.30(10) . . ?
C17 N18 H18 117.6(10) . . ?
C19 N18 H18 115.4(10) . . ?
N18 C19 C28 112.80(10) . . ?
N18 C19 C20 111.21(10) . . ?
C28 C19 C20 109.68(10) . . ?
N18 C19 C26 106.44(10) . . ?
C28 C19 C26 108.57(10) . . ?
C20 C19 C26 107.94(10) . . ?
C19 C20 C21 109.80(10) . . ?
C19 C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C27 C21 C22 109.85(12) . . ?
C27 C21 C20 109.69(11) . . ?
C22 C21 C20 109.38(11) . . ?
C27 C21 H21 109.3 . . ?
C22 C21 H21 109.3 . . ?
C20 C21 H21 109.3 . . ?
C21 C22 C23 109.36(11) . . ?
C21 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
C21 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C22 110.00(12) . . ?
C24 C23 C28 109.47(11) . . ?
C22 C23 C28 109.23(11) . . ?
C24 C23 H23 109.4 . . ?
C22 C23 H23 109.4 . . ?
C28 C23 H23 109.4 . . ?
C23 C24 C25 109.28(11) . . ?
C23 C24 H24A 109.8 . . ?
C25 C24 H24A 109.8 . . ?
C23 C24 H24B 109.8 . . ?
C25 C24 H24B 109.8 . . ?
H24A C24 H24B 108.3 . . ?
C27 C25 C24 108.97(12) . . ?
C27 C25 C26 109.56(12) . . ?
C24 C25 C26 109.89(11) . . ?
C27 C25 H25 109.5 . . ?
C24 C25 H25 109.5 . . ?
C26 C25 H25 109.5 . . ?
C25 C26 C19 110.46(10) . . ?
C25 C26 H26A 109.6 . . ?
C19 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
C19 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
C21 C27 C25 109.30(11) . . ?
C21 C27 H27A 109.8 . . ?
C25 C27 H27A 109.8 . . ?
C21 C27 H27B 109.8 . . ?
C25 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
C19 C28 C23 110.00(10) . . ?
C19 C28 H28A 109.7 . . ?
C23 C28 H28A 109.7 . . ?
C19 C28 H28B 109.7 . . ?
C23 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?

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
C17 N1 C2 C10 -1.74(19) . . . . ?
C17 N1 C2 N3 179.93(11) . . . . ?
N1 C2 N3 C4 1.3(2) . . . . ?
C10 C2 N3 C4 -177.35(12) . . . . ?
N1 C2 N3 C8 178.89(11) . . . . ?
C10 C2 N3 C8 0.22(13) . . . . ?
C2 N3 C4 C5 177.55(12) . . . . ?
C8 N3 C4 C5 0.34(19) . . . . ?
N3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C4 N3 C8 N9 178.54(11) . . . . ?
C2 N3 C8 N9 0.74(14) . . . . ?
C4 N3 C8 C7 -1.33(18) . . . . ?
C2 N3 C8 C7 -179.13(11) . . . . ?
C6 C7 C8 N9 -178.47(14) . . . . ?
C6 C7 C8 N3 1.37(19) . . . . ?
N3 C8 N9 C10 -1.36(14) . . . . ?
C7 C8 N9 C10 178.49(13) . . . . ?
C8 N9 C10 C2 1.52(14) . . . . ?
C8 N9 C10 C11 -178.13(13) . . . . ?
N1 C2 C10 N9 -179.67(12) . . . . ?
N3 C2 C10 N9 -1.10(14) . . . . ?
N1 C2 C10 C11 0.0(2) . . . . ?
N3 C2 C10 C11 178.61(10) . . . . ?
N9 C10 C11 C12 1.6(2) . . . . ?
C2 C10 C11 C12 -178.06(12) . . . . ?
N9 C10 C11 C16 -177.87(12) . . . . ?
C2 C10 C11 C16 2.49(16) . . . . ?
C16 C11 C12 C13 1.7(2) . . . . ?
C10 C11 C12 C13 -177.72(13) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 -1.1(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 2.38(19) . . . . ?
C14 C15 C16 C17 -177.95(12) . . . . ?
C12 C11 C16 C15 -3.05(17) . . . . ?
C10 C11 C16 C15 176.42(11) . . . . ?
C12 C11 C16 C17 177.26(11) . . . . ?
C10 C11 C16 C17 -3.26(16) . . . . ?
C2 N1 C17 N18 -179.22(11) . . . . ?
C2 N1 C17 C16 0.83(17) . . . . ?
C15 C16 C17 N1 -178.03(12) . . . . ?
C11 C16 C17 N1 1.64(18) . . . . ?
C15 C16 C17 N18 2.02(18) . . . . ?
C11 C16 C17 N18 -178.31(11) . . . . ?
N1 C17 N18 C19 9.71(19) . . . . ?
C16 C17 N18 C19 -170.34(11) . . . . ?
C17 N18 C19 C28 -67.77(16) . . . . ?
C17 N18 C19 C20 55.94(16) . . . . ?
C17 N18 C19 C26 173.27(12) . . . . ?
N18 C19 C20 C21 176.31(10) . . . . ?
C28 C19 C20 C21 -58.22(13) . . . . ?
C26 C19 C20 C21 59.90(13) . . . . ?
C19 C20 C21 C27 -60.80(15) . . . . ?
C19 C20 C21 C22 59.75(14) . . . . ?
C27 C21 C22 C23 59.27(14) . . . . ?
C20 C21 C22 C23 -61.18(14) . . . . ?
C21 C22 C23 C24 -59.07(14) . . . . ?
C21 C22 C23 C28 61.10(14) . . . . ?
C22 C23 C24 C25 59.95(15) . . . . ?
C28 C23 C24 C25 -60.08(15) . . . . ?
C23 C24 C25 C27 -60.55(15) . . . . ?
C23 C24 C25 C26 59.50(15) . . . . ?
C27 C25 C26 C19 60.29(15) . . . . ?
C24 C25 C26 C19 -59.40(15) . . . . ?
N18 C19 C26 C25 -179.48(11) . . . . ?
C28 C19 C26 C25 58.83(14) . . . . ?
C20 C19 C26 C25 -60.00(14) . . . . ?
C22 C21 C27 C25 -60.46(15) . . . . ?
C20 C21 C27 C25 59.80(15) . . . . ?
C24 C25 C27 C21 60.85(14) . . . . ?
C26 C25 C27 C21 -59.41(15) . . . . ?
N18 C19 C28 C23 -177.10(10) . . . . ?
C20 C19 C28 C23 58.35(13) . . . . ?
C26 C19 C28 C23 -59.38(13) . . . . ?
C24 C23 C28 C19 60.73(15) . . . . ?
C22 C23 C28 C19 -59.77(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N18 H18 N9 0.891(16) 2.781(16) 3.6319(16) 160.3(13) 2_556

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_sb1132_hy_compound_10a
_database_code_depnum_ccdc_archive 'CCDC 2152373'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2022-02-16 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
N-cyclohexylpyrazino[2',1':2,3]imidazo[4,5-c]isoquinolin-5-amine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N5'
_chemical_formula_sum            'C19 H19 N5'
_chemical_formula_weight         317.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.7193(2)
_cell_length_b                   19.0741(6)
_cell_length_c                   10.7854(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.055(1)
_cell_angle_gamma                90
_cell_volume                     1546.98(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      4.8
_cell_measurement_theta_max      72.2

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.669
_shelx_estimated_absorpt_T_min   0.825
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8151
_exptl_absorpt_correction_T_max  0.8154
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 15+1 runs, 2600 frames, 8/12/20 sec./frame
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27211
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.805
_diffrn_reflns_theta_max         72.251
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3049
_reflns_number_gt                2978
_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       APEX3
_computing_cell_refinement       APEX3
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  publCIF

_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)+(0.0391P)²+0.6426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3049
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
N1 N 0.28872(11) 0.52361(4) 0.37949(8) 0.01773(19) Uani 1 1 d . . . . .
C2 C 0.25301(13) 0.49968(5) 0.26120(10) 0.0169(2) Uani 1 1 d . . . . .
C2A C 0.18204(13) 0.42899(5) 0.22676(10) 0.0176(2) Uani 1 1 d . . . . .
C3 C 0.16817(14) 0.40115(6) 0.10413(10) 0.0210(2) Uani 1 1 d . . . . .
H3 H 0.2010 0.4290 0.0401 0.025 Uiso 1 1 calc R U . . .
C4 C 0.10717(14) 0.33366(6) 0.07603(10) 0.0232(2) Uani 1 1 d . . . . .
H4 H 0.1013 0.3152 -0.0066 0.028 Uiso 1 1 calc R U . . .
C5 C 0.05395(14) 0.29219(6) 0.16779(11) 0.0227(2) Uani 1 1 d . . . . .
H5 H 0.0112 0.2460 0.1472 0.027 Uiso 1 1 calc R U . . .
C6 C 0.06358(14) 0.31846(6) 0.28798(10) 0.0210(2) Uani 1 1 d . . . . .
H6 H 0.0251 0.2906 0.3496 0.025 Uiso 1 1 calc R U . . .
C6A C 0.12999(13) 0.38634(5) 0.32024(10) 0.0179(2) Uani 1 1 d . . . . .
C6B C 0.15368(13) 0.41596(5) 0.44510(10) 0.0178(2) Uani 1 1 d . . . . .
N7 N 0.10978(11) 0.39119(5) 0.55394(8) 0.0201(2) Uani 1 1 d . . . . .
C7A C 0.16633(13) 0.44133(5) 0.63939(10) 0.0183(2) Uani 1 1 d . . . . .
C8 C 0.16055(14) 0.44783(6) 0.76929(10) 0.0210(2) Uani 1 1 d . . . . .
H8 H 0.1037 0.4118 0.8063 0.025 Uiso 1 1 calc R U . . .
N9 N 0.22953(12) 0.50102(5) 0.84147(9) 0.0230(2) Uani 1 1 d . . . . .
C10 C 0.30797(15) 0.55346(6) 0.78517(10) 0.0230(2) Uani 1 1 d . . . . .
H10 H 0.3586 0.5920 0.8365 0.028 Uiso 1 1 calc R U . . .
C11 C 0.31738(14) 0.55344(5) 0.66160(10) 0.0205(2) Uani 1 1 d . . . . .
H11 H 0.3713 0.5911 0.6265 0.025 Uiso 1 1 calc R U . . .
N11A N 0.24613(11) 0.49706(4) 0.58865(8) 0.01738(19) Uani 1 1 d . . . . .
C11B C 0.23605(13) 0.48096(5) 0.46350(9) 0.0172(2) Uani 1 1 d . . . . .
N21 N 0.28478(12) 0.54383(4) 0.17018(8) 0.01881(19) Uani 1 1 d D . . . .
H21 H 0.2679(17) 0.5294(7) 0.0897(11) 0.023 Uiso 1 1 d D U . . .
C22 C 0.37950(13) 0.61008(5) 0.20422(9) 0.0170(2) Uani 1 1 d . . . . .
H22 H 0.4851 0.6004 0.2750 0.020 Uiso 1 1 calc R U . . .
C23 C 0.26745(14) 0.66664(5) 0.24964(10) 0.0199(2) Uani 1 1 d . . . . .
H23A H 0.1638 0.6785 0.1803 0.024 Uiso 1 1 calc R U . . .
H23B H 0.2228 0.6489 0.3229 0.024 Uiso 1 1 calc R U . . .
C24 C 0.38154(15) 0.73199(6) 0.28900(11) 0.0239(2) Uani 1 1 d . . . . .
H24A H 0.3086 0.7688 0.3173 0.029 Uiso 1 1 calc R U . . .
H24B H 0.4810 0.7203 0.3616 0.029 Uiso 1 1 calc R U . . .
C25 C 0.45625(15) 0.76013(6) 0.17940(11) 0.0250(2) Uani 1 1 d . . . . .
H25A H 0.5358 0.8003 0.2095 0.030 Uiso 1 1 calc R U . . .
H25B H 0.3575 0.7769 0.1105 0.030 Uiso 1 1 calc R U . . .
C26 C 0.55979(14) 0.70311(6) 0.12762(11) 0.0225(2) Uani 1 1 d . . . . .
H26A H 0.5981 0.7212 0.0520 0.027 Uiso 1 1 calc R U . . .
H26B H 0.6677 0.6910 0.1931 0.027 Uiso 1 1 calc R U . . .
C27 C 0.44709(14) 0.63742(5) 0.09091(10) 0.0195(2) Uani 1 1 d . . . . .
H27A H 0.3448 0.6485 0.0200 0.023 Uiso 1 1 calc R U . . .
H27B H 0.5192 0.6007 0.0615 0.023 Uiso 1 1 calc R U . . .


_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
N1 C2 1.3240(13) . ?
N1 C11B 1.3471(13) . ?
C2 N21 1.3571(13) . ?
C2 C2A 1.4711(14) . ?
C2A C3 1.4066(15) . ?
C2A C6A 1.4223(14) . ?
C3 C4 1.3807(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3992(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3759(15) . ?
C5 H5 0.9500 . ?
C6 C6A 1.4070(14) . ?
C6 H6 0.9500 . ?
C6A C6B 1.4335(14) . ?
C6B N7 1.3770(13) . ?
C6B C11B 1.3871(14) . ?
N7 C7A 1.3315(14) . ?
C7A N11A 1.4004(13) . ?
C7A C8 1.4173(15) . ?
C8 N9 1.3158(15) . ?
C8 H8 0.9500 . ?
N9 C10 1.3791(15) . ?
C10 C11 1.3510(15) . ?
C10 H10 0.9500 . ?
C11 N11A 1.3721(13) . ?
C11 H11 0.9500 . ?
N11A C11B 1.3692(13) . ?
N21 C22 1.4647(13) . ?
N21 H21 0.892(11) . ?
C22 C27 1.5251(14) . ?
C22 C23 1.5308(14) . ?
C22 H22 1.0000 . ?
C23 C24 1.5300(14) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5250(16) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5282(15) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.5258(14) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 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
C2 N1 C11B 114.28(9) . . ?
N1 C2 N21 116.79(9) . . ?
N1 C2 C2A 122.95(9) . . ?
N21 C2 C2A 120.25(9) . . ?
C3 C2A C6A 118.48(9) . . ?
C3 C2A C2 121.89(9) . . ?
C6A C2A C2 119.60(9) . . ?
C4 C3 C2A 120.54(10) . . ?
C4 C3 H3 119.7 . . ?
C2A C3 H3 119.7 . . ?
C3 C4 C5 120.79(10) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.90(10) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C6A 120.47(10) . . ?
C5 C6 H6 119.8 . . ?
C6A C6 H6 119.8 . . ?
C6 C6A C2A 119.77(9) . . ?
C6 C6A C6B 123.86(9) . . ?
C2A C6A C6B 116.35(9) . . ?
N7 C6B C11B 112.20(9) . . ?
N7 C6B C6A 131.44(9) . . ?
C11B C6B C6A 116.35(9) . . ?
C7A N7 C6B 103.78(8) . . ?
N7 C7A N11A 112.28(9) . . ?
N7 C7A C8 131.95(10) . . ?
N11A C7A C8 115.77(9) . . ?
N9 C8 C7A 123.60(10) . . ?
N9 C8 H8 118.2 . . ?
C7A C8 H8 118.2 . . ?
C8 N9 C10 117.26(9) . . ?
C11 C10 N9 124.12(10) . . ?
C11 C10 H10 117.9 . . ?
N9 C10 H10 117.9 . . ?
C10 C11 N11A 117.52(10) . . ?
C10 C11 H11 121.2 . . ?
N11A C11 H11 121.2 . . ?
C11B N11A C11 131.85(9) . . ?
C11B N11A C7A 106.44(8) . . ?
C11 N11A C7A 121.70(9) . . ?
N1 C11B N11A 124.69(9) . . ?
N1 C11B C6B 129.92(9) . . ?
N11A C11B C6B 105.29(9) . . ?
C2 N21 C22 121.04(8) . . ?
C2 N21 H21 120.2(9) . . ?
C22 N21 H21 117.7(8) . . ?
N21 C22 C27 109.63(8) . . ?
N21 C22 C23 113.71(8) . . ?
C27 C22 C23 109.62(8) . . ?
N21 C22 H22 107.9 . . ?
C27 C22 H22 107.9 . . ?
C23 C22 H22 107.9 . . ?
C24 C23 C22 109.36(8) . . ?
C24 C23 H23A 109.8 . . ?
C22 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
C22 C23 H23B 109.8 . . ?
H23A C23 H23B 108.3 . . ?
C25 C24 C23 111.50(9) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 110.70(9) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C27 C26 C25 111.38(9) . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C22 C27 C26 110.55(8) . . ?
C22 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?

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
C11B N1 C2 N21 172.80(9) . . . . ?
C11B N1 C2 C2A -7.12(14) . . . . ?
N1 C2 C2A C3 -171.06(10) . . . . ?
N21 C2 C2A C3 9.02(15) . . . . ?
N1 C2 C2A C6A 7.21(15) . . . . ?
N21 C2 C2A C6A -172.72(9) . . . . ?
C6A C2A C3 C4 -0.70(15) . . . . ?
C2 C2A C3 C4 177.59(9) . . . . ?
C2A C3 C4 C5 1.54(16) . . . . ?
C3 C4 C5 C6 -0.55(16) . . . . ?
C4 C5 C6 C6A -1.28(16) . . . . ?
C5 C6 C6A C2A 2.10(15) . . . . ?
C5 C6 C6A C6B -176.33(10) . . . . ?
C3 C2A C6A C6 -1.10(14) . . . . ?
C2 C2A C6A C6 -179.42(9) . . . . ?
C3 C2A C6A C6B 177.45(9) . . . . ?
C2 C2A C6A C6B -0.87(13) . . . . ?
C6 C6A C6B N7 -5.36(17) . . . . ?
C2A C6A C6B N7 176.16(10) . . . . ?
C6 C6A C6B C11B 174.17(9) . . . . ?
C2A C6A C6B C11B -4.31(13) . . . . ?
C11B C6B N7 C7A -0.20(11) . . . . ?
C6A C6B N7 C7A 179.34(10) . . . . ?
C6B N7 C7A N11A -0.45(11) . . . . ?
C6B N7 C7A C8 179.80(11) . . . . ?
N7 C7A C8 N9 177.61(10) . . . . ?
N11A C7A C8 N9 -2.13(15) . . . . ?
C7A C8 N9 C10 1.36(15) . . . . ?
C8 N9 C10 C11 0.23(16) . . . . ?
N9 C10 C11 N11A -0.89(16) . . . . ?
C10 C11 N11A C11B -179.15(10) . . . . ?
C10 C11 N11A C7A 0.00(15) . . . . ?
N7 C7A N11A C11B 0.94(11) . . . . ?
C8 C7A N11A C11B -179.27(9) . . . . ?
N7 C7A N11A C11 -178.40(9) . . . . ?
C8 C7A N11A C11 1.39(14) . . . . ?
C2 N1 C11B N11A -174.65(9) . . . . ?
C2 N1 C11B C6B 1.22(15) . . . . ?
C11 N11A C11B N1 -5.02(17) . . . . ?
C7A N11A C11B N1 175.73(9) . . . . ?
C11 N11A C11B C6B 178.27(10) . . . . ?
C7A N11A C11B C6B -0.99(10) . . . . ?
N7 C6B C11B N1 -175.71(10) . . . . ?
C6A C6B C11B N1 4.67(16) . . . . ?
N7 C6B C11B N11A 0.77(11) . . . . ?
C6A C6B C11B N11A -178.85(8) . . . . ?
N1 C2 N21 C22 9.23(14) . . . . ?
C2A C2 N21 C22 -170.84(8) . . . . ?
C2 N21 C22 C27 162.36(9) . . . . ?
C2 N21 C22 C23 -74.54(12) . . . . ?
N21 C22 C23 C24 177.12(8) . . . . ?
C27 C22 C23 C24 -59.78(11) . . . . ?
C22 C23 C24 C25 58.29(11) . . . . ?
C23 C24 C25 C26 -55.35(12) . . . . ?
C24 C25 C26 C27 54.16(12) . . . . ?
N21 C22 C27 C26 -175.15(8) . . . . ?
C23 C22 C27 C26 59.37(11) . . . . ?
C25 C26 C27 C22 -56.64(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 N9 0.892(11) 2.681(12) 3.5685(13) 173.3(11) 1_554
C23 H23B N1 0.99 2.49 3.0540(13) 115.7 .

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.036

