# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2103232'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 F3 N3'
_chemical_formula_sum            'C19 H24 F3 N3'
_chemical_formula_weight         351.41

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.2027(18)
_cell_length_b                   11.891(4)
_cell_length_c                   12.512(4)
_cell_angle_alpha                68.122(8)
_cell_angle_beta                 76.813(8)
_cell_angle_gamma                86.440(8)
_cell_volume                     833.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    95(2)
_cell_measurement_reflns_used    1118
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      24.58


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1996
_exptl_absorpt_correction_T_max  0.7454
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0640
0.00 1.00 0.00 0.0800
1.00 -1.00 0.00 0.1640
-1.00 1.00 0.00 0.1650
1.00 0.00 -1.00 0.1580
-1.00 0.00 1.00 0.1530
0.00 0.00 -1.00 0.0640
0.00 0.00 1.00 0.1090
1.00 1.00 0.00 0.1730
-1.00 -1.00 0.00 0.1550
1.00 1.00 -1.00 0.1600
-1.00 -1.00 -1.00 0.1770
-1.00 0.00 -1.00 0.1780
1.00 0.00 1.00 0.1370
-1.00 1.00 1.00 0.1750
1.00 -1.00 -1.00 0.1590
-1.00 -1.00 1.00 0.1430

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      95(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            9142
_diffrn_reflns_av_unetI/netI     0.1890
_diffrn_reflns_av_R_equivalents  0.1352
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.048
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3408
_reflns_number_gt                1866
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3408
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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
C1_1 C 0.6166(6) 0.1624(3) 0.3626(3) 0.0196(8) Uani 1 1 d . . . . .
C2_1 C 0.3999(5) 0.1982(3) 0.4296(3) 0.0195(8) Uani 1 1 d . . . . .
H2_1 H 0.273918 0.146915 0.434078 0.023 Uiso 1 1 calc R U . . .
C3_1 C 0.4554(6) 0.1595(3) 0.5500(3) 0.0214(8) Uani 1 1 d . . . . .
C4_1 C 0.6715(6) 0.1170(3) 0.5391(3) 0.0210(8) Uani 1 1 d . . . . .
N5_1 N 0.7672(5) 0.1187(2) 0.4253(2) 0.0219(7) Uani 1 1 d . . . . .
C7_1 C 0.7742(6) 0.0779(3) 0.6344(3) 0.0226(8) Uani 1 1 d . . . . .
H7_1 H 0.920287 0.047904 0.627165 0.027 Uiso 1 1 calc R U . . .
C8_1 C 0.6554(6) 0.0842(3) 0.7406(3) 0.0243(8) Uani 1 1 d . . . . .
H8_1 H 0.722992 0.060080 0.806397 0.029 Uiso 1 1 calc R U . . .
C9_1 C 0.4395(6) 0.1251(3) 0.7523(3) 0.0222(8) Uani 1 1 d . . . . .
C10_1 C 0.3366(6) 0.1630(3) 0.6567(3) 0.0216(8) Uani 1 1 d . . . . .
H10_1 H 0.188770 0.190412 0.664747 0.026 Uiso 1 1 calc R U . . .
C1_2 C 0.3199(6) 0.1281(3) 0.8687(3) 0.0271(9) Uani 1 1 d . . . . .
F1_2 F 0.2796(4) 0.01684(17) 0.95447(16) 0.0369(6) Uani 1 1 d . . . . .
F2_2 F 0.4329(3) 0.18903(17) 0.91154(17) 0.0352(6) Uani 1 1 d . . . . .
F3_2 F 0.1224(4) 0.1804(2) 0.86574(18) 0.0432(6) Uani 1 1 d . . . . .
N1_3 N 0.6510(5) 0.1788(2) 0.2481(2) 0.0222(7) Uani 1 1 d . . . . .
C2_3 C 0.9547(6) 0.2919(3) 0.0875(3) 0.0285(9) Uani 1 1 d . . . . .
H2A_3 H 0.974304 0.348133 0.126417 0.034 Uiso 1 1 calc R U . . .
H2AB_3 H 1.100166 0.283756 0.038477 0.034 Uiso 1 1 calc R U . . .
C3_3 C 0.7904(6) 0.3437(3) 0.0089(3) 0.0292(9) Uani 1 1 d . . . . .
H3A_3 H 0.788397 0.293971 -0.039065 0.035 Uiso 1 1 calc R U . . .
H3AB_3 H 0.839189 0.427115 -0.045804 0.035 Uiso 1 1 calc R U . . .
C4_3 C 0.5587(6) 0.3465(3) 0.0802(3) 0.0255(8) Uani 1 1 d . . . . .
H4A_3 H 0.453798 0.370985 0.027023 0.031 Uiso 1 1 calc R U . . .
H4AB_3 H 0.554424 0.407354 0.117171 0.031 Uiso 1 1 calc R U . . .
C5_3 C 0.4878(6) 0.2231(3) 0.1755(3) 0.0242(8) Uani 1 1 d . . . . .
H5A_3 H 0.342763 0.229241 0.226014 0.029 Uiso 1 1 calc R U . . .
H5AB_3 H 0.470172 0.164889 0.138355 0.029 Uiso 1 1 calc R U . . .
C1_3 C 0.8734(6) 0.1675(3) 0.1817(3) 0.0254(8) Uani 1 1 d . . . . .
H1A_3 H 0.869348 0.108391 0.143537 0.030 Uiso 1 1 calc R U . . .
H1AB_3 H 0.975936 0.137923 0.235891 0.030 Uiso 1 1 calc R U . . .
C1_4 C 0.1357(5) 0.3604(3) 0.4185(3) 0.0235(8) Uani 1 1 d . . . . .
H1A_4 H 0.127570 0.356267 0.499803 0.028 Uiso 1 1 calc R U . . .
H1AB_4 H 0.023523 0.302715 0.421934 0.028 Uiso 1 1 calc R U . . .
N1_4 N 0.3561(4) 0.3270(2) 0.3698(2) 0.0199(7) Uani 1 1 d . . . . .
C2_4 C 0.0869(6) 0.4879(3) 0.3419(3) 0.0244(8) Uani 1 1 d . . . . .
H2A_4 H -0.061033 0.510671 0.376793 0.029 Uiso 1 1 calc R U . . .
H2AB_4 H 0.084206 0.490214 0.262301 0.029 Uiso 1 1 calc R U . . .
C3_4 C 0.2615(6) 0.5791(3) 0.3312(3) 0.0257(8) Uani 1 1 d . . . . .
H3A_4 H 0.235584 0.659837 0.273973 0.031 Uiso 1 1 calc R U . . .
H3AB_4 H 0.249016 0.586225 0.408704 0.031 Uiso 1 1 calc R U . . .
C4_4 C 0.4922(6) 0.5386(3) 0.2901(3) 0.0252(8) Uani 1 1 d . . . . .
H4A_4 H 0.604150 0.592885 0.292582 0.030 Uiso 1 1 calc R U . . .
H4AB_4 H 0.512590 0.544254 0.207412 0.030 Uiso 1 1 calc R U . . .
C5_4 C 0.5265(6) 0.4080(3) 0.3688(3) 0.0234(8) Uani 1 1 d . . . . .
H5A_4 H 0.675086 0.381821 0.338892 0.028 Uiso 1 1 calc R U . . .
H5AB_4 H 0.518452 0.403508 0.450247 0.028 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
C1_1 N5_1 1.314(4) . ?
C1_1 N1_3 1.340(4) . ?
C1_1 C2_1 1.540(4) . ?
C2_1 N1_4 1.472(4) . ?
C2_1 C3_1 1.516(5) . ?
C2_1 H2_1 1.0000 . ?
C3_1 C10_1 1.384(4) . ?
C3_1 C4_1 1.399(5) . ?
C4_1 C7_1 1.393(5) . ?
C4_1 N5_1 1.405(4) . ?
C7_1 C8_1 1.391(4) . ?
C7_1 H7_1 0.9500 . ?
C8_1 C9_1 1.391(5) . ?
C8_1 H8_1 0.9500 . ?
C9_1 C10_1 1.398(5) . ?
C9_1 C1_2 1.488(4) . ?
C10_1 H10_1 0.9500 . ?
C1_2 F3_2 1.340(4) . ?
C1_2 F2_2 1.352(4) . ?
C1_2 F1_2 1.351(4) . ?
N1_3 C5_3 1.458(4) . ?
N1_3 C1_3 1.466(4) . ?
C2_3 C3_3 1.520(5) . ?
C2_3 C1_3 1.534(4) . ?
C2_3 H2A_3 0.9900 . ?
C2_3 H2AB_3 0.9900 . ?
C3_3 C4_3 1.514(5) . ?
C3_3 H3A_3 0.9900 . ?
C3_3 H3AB_3 0.9900 . ?
C4_3 C5_3 1.518(4) . ?
C4_3 H4A_3 0.9900 . ?
C4_3 H4AB_3 0.9900 . ?
C5_3 H5A_3 0.9900 . ?
C5_3 H5AB_3 0.9900 . ?
C1_3 H1A_3 0.9900 . ?
C1_3 H1AB_3 0.9900 . ?
C1_4 N1_4 1.460(4) . ?
C1_4 C2_4 1.516(4) . ?
C1_4 H1A_4 0.9900 . ?
C1_4 H1AB_4 0.9900 . ?
N1_4 C5_4 1.468(4) . ?
C2_4 C3_4 1.529(4) . ?
C2_4 H2A_4 0.9900 . ?
C2_4 H2AB_4 0.9900 . ?
C3_4 C4_4 1.519(5) . ?
C3_4 H3A_4 0.9900 . ?
C3_4 H3AB_4 0.9900 . ?
C4_4 C5_4 1.530(4) . ?
C4_4 H4A_4 0.9900 . ?
C4_4 H4AB_4 0.9900 . ?
C5_4 H5A_4 0.9900 . ?
C5_4 H5AB_4 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
N5_1 C1_1 N1_3 122.8(3) . . ?
N5_1 C1_1 C2_1 114.9(3) . . ?
N1_3 C1_1 C2_1 122.3(3) . . ?
N1_4 C2_1 C3_1 118.0(2) . . ?
N1_4 C2_1 C1_1 110.5(2) . . ?
C3_1 C2_1 C1_1 98.6(3) . . ?
N1_4 C2_1 H2_1 109.7 . . ?
C3_1 C2_1 H2_1 109.7 . . ?
C1_1 C2_1 H2_1 109.7 . . ?
C10_1 C3_1 C4_1 120.7(3) . . ?
C10_1 C3_1 C2_1 132.1(3) . . ?
C4_1 C3_1 C2_1 107.3(3) . . ?
C7_1 C4_1 C3_1 121.3(3) . . ?
C7_1 C4_1 N5_1 125.5(3) . . ?
C3_1 C4_1 N5_1 113.3(3) . . ?
C1_1 N5_1 C4_1 105.9(3) . . ?
C4_1 C7_1 C8_1 117.7(3) . . ?
C4_1 C7_1 H7_1 121.2 . . ?
C8_1 C7_1 H7_1 121.2 . . ?
C9_1 C8_1 C7_1 121.3(3) . . ?
C9_1 C8_1 H8_1 119.4 . . ?
C7_1 C8_1 H8_1 119.4 . . ?
C8_1 C9_1 C10_1 120.7(3) . . ?
C8_1 C9_1 C1_2 118.8(3) . . ?
C10_1 C9_1 C1_2 120.5(3) . . ?
C3_1 C10_1 C9_1 118.4(3) . . ?
C3_1 C10_1 H10_1 120.8 . . ?
C9_1 C10_1 H10_1 120.8 . . ?
F3_2 C1_2 F2_2 105.9(3) . . ?
F3_2 C1_2 F1_2 105.9(3) . . ?
F2_2 C1_2 F1_2 104.6(3) . . ?
F3_2 C1_2 C9_1 113.1(3) . . ?
F2_2 C1_2 C9_1 113.3(3) . . ?
F1_2 C1_2 C9_1 113.2(3) . . ?
C1_1 N1_3 C5_3 125.1(3) . . ?
C1_1 N1_3 C1_3 120.4(3) . . ?
C5_3 N1_3 C1_3 114.0(3) . . ?
C3_3 C2_3 C1_3 110.9(3) . . ?
C3_3 C2_3 H2A_3 109.5 . . ?
C1_3 C2_3 H2A_3 109.5 . . ?
C3_3 C2_3 H2AB_3 109.5 . . ?
C1_3 C2_3 H2AB_3 109.5 . . ?
H2A_3 C2_3 H2AB_3 108.1 . . ?
C2_3 C3_3 C4_3 111.9(3) . . ?
C2_3 C3_3 H3A_3 109.2 . . ?
C4_3 C3_3 H3A_3 109.2 . . ?
C2_3 C3_3 H3AB_3 109.2 . . ?
C4_3 C3_3 H3AB_3 109.2 . . ?
H3A_3 C3_3 H3AB_3 107.9 . . ?
C3_3 C4_3 C5_3 111.0(3) . . ?
C3_3 C4_3 H4A_3 109.4 . . ?
C5_3 C4_3 H4A_3 109.4 . . ?
C3_3 C4_3 H4AB_3 109.4 . . ?
C5_3 C4_3 H4AB_3 109.4 . . ?
H4A_3 C4_3 H4AB_3 108.0 . . ?
N1_3 C5_3 C4_3 110.8(3) . . ?
N1_3 C5_3 H5A_3 109.5 . . ?
C4_3 C5_3 H5A_3 109.5 . . ?
N1_3 C5_3 H5AB_3 109.5 . . ?
C4_3 C5_3 H5AB_3 109.5 . . ?
H5A_3 C5_3 H5AB_3 108.1 . . ?
N1_3 C1_3 C2_3 109.0(3) . . ?
N1_3 C1_3 H1A_3 109.9 . . ?
C2_3 C1_3 H1A_3 109.9 . . ?
N1_3 C1_3 H1AB_3 109.9 . . ?
C2_3 C1_3 H1AB_3 109.9 . . ?
H1A_3 C1_3 H1AB_3 108.3 . . ?
N1_4 C1_4 C2_4 110.0(3) . . ?
N1_4 C1_4 H1A_4 109.7 . . ?
C2_4 C1_4 H1A_4 109.7 . . ?
N1_4 C1_4 H1AB_4 109.7 . . ?
C2_4 C1_4 H1AB_4 109.7 . . ?
H1A_4 C1_4 H1AB_4 108.2 . . ?
C1_4 N1_4 C2_1 112.5(2) . . ?
C1_4 N1_4 C5_4 110.7(2) . . ?
C2_1 N1_4 C5_4 112.5(3) . . ?
C1_4 C2_4 C3_4 111.1(3) . . ?
C1_4 C2_4 H2A_4 109.4 . . ?
C3_4 C2_4 H2A_4 109.4 . . ?
C1_4 C2_4 H2AB_4 109.4 . . ?
C3_4 C2_4 H2AB_4 109.4 . . ?
H2A_4 C2_4 H2AB_4 108.0 . . ?
C4_4 C3_4 C2_4 110.3(3) . . ?
C4_4 C3_4 H3A_4 109.6 . . ?
C2_4 C3_4 H3A_4 109.6 . . ?
C4_4 C3_4 H3AB_4 109.6 . . ?
C2_4 C3_4 H3AB_4 109.6 . . ?
H3A_4 C3_4 H3AB_4 108.1 . . ?
C3_4 C4_4 C5_4 110.6(3) . . ?
C3_4 C4_4 H4A_4 109.5 . . ?
C5_4 C4_4 H4A_4 109.5 . . ?
C3_4 C4_4 H4AB_4 109.5 . . ?
C5_4 C4_4 H4AB_4 109.5 . . ?
H4A_4 C4_4 H4AB_4 108.1 . . ?
N1_4 C5_4 C4_4 110.2(3) . . ?
N1_4 C5_4 H5A_4 109.6 . . ?
C4_4 C5_4 H5A_4 109.6 . . ?
N1_4 C5_4 H5AB_4 109.6 . . ?
C4_4 C5_4 H5AB_4 109.6 . . ?
H5A_4 C5_4 H5AB_4 108.1 . . ?

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
N5_1 C1_1 C2_1 N1_4 122.0(3) . . . . ?
N1_3 C1_1 C2_1 N1_4 -55.7(4) . . . . ?
N5_1 C1_1 C2_1 C3_1 -2.4(3) . . . . ?
N1_3 C1_1 C2_1 C3_1 179.9(3) . . . . ?
N1_4 C2_1 C3_1 C10_1 61.9(4) . . . . ?
C1_1 C2_1 C3_1 C10_1 -179.3(3) . . . . ?
N1_4 C2_1 C3_1 C4_1 -116.4(3) . . . . ?
C1_1 C2_1 C3_1 C4_1 2.4(3) . . . . ?
C10_1 C3_1 C4_1 C7_1 -0.5(4) . . . . ?
C2_1 C3_1 C4_1 C7_1 178.0(3) . . . . ?
C10_1 C3_1 C4_1 N5_1 179.5(2) . . . . ?
C2_1 C3_1 C4_1 N5_1 -2.0(3) . . . . ?
N1_3 C1_1 N5_1 C4_1 179.0(3) . . . . ?
C2_1 C1_1 N5_1 C4_1 1.4(3) . . . . ?
C7_1 C4_1 N5_1 C1_1 -179.6(3) . . . . ?
C3_1 C4_1 N5_1 C1_1 0.4(3) . . . . ?
C3_1 C4_1 C7_1 C8_1 -0.9(4) . . . . ?
N5_1 C4_1 C7_1 C8_1 179.1(3) . . . . ?
C4_1 C7_1 C8_1 C9_1 1.6(4) . . . . ?
C7_1 C8_1 C9_1 C10_1 -1.0(4) . . . . ?
C7_1 C8_1 C9_1 C1_2 179.1(3) . . . . ?
C4_1 C3_1 C10_1 C9_1 1.2(4) . . . . ?
C2_1 C3_1 C10_1 C9_1 -176.9(3) . . . . ?
C8_1 C9_1 C10_1 C3_1 -0.5(4) . . . . ?
C1_2 C9_1 C10_1 C3_1 179.4(3) . . . . ?
C8_1 C9_1 C1_2 F3_2 173.7(3) . . . . ?
C10_1 C9_1 C1_2 F3_2 -6.2(4) . . . . ?
C8_1 C9_1 C1_2 F2_2 53.1(4) . . . . ?
C10_1 C9_1 C1_2 F2_2 -126.8(3) . . . . ?
C8_1 C9_1 C1_2 F1_2 -65.8(4) . . . . ?
C10_1 C9_1 C1_2 F1_2 114.3(3) . . . . ?
N5_1 C1_1 N1_3 C5_3 177.9(3) . . . . ?
C2_1 C1_1 N1_3 C5_3 -4.6(4) . . . . ?
N5_1 C1_1 N1_3 C1_3 -10.3(4) . . . . ?
C2_1 C1_1 N1_3 C1_3 167.2(3) . . . . ?
C1_3 C2_3 C3_3 C4_3 53.4(4) . . . . ?
C2_3 C3_3 C4_3 C5_3 -52.1(4) . . . . ?
C1_1 N1_3 C5_3 C4_3 113.8(3) . . . . ?
C1_3 N1_3 C5_3 C4_3 -58.5(3) . . . . ?
C3_3 C4_3 C5_3 N1_3 53.3(4) . . . . ?
C1_1 N1_3 C1_3 C2_3 -113.8(3) . . . . ?
C5_3 N1_3 C1_3 C2_3 59.0(3) . . . . ?
C3_3 C2_3 C1_3 N1_3 -55.1(4) . . . . ?
C2_4 C1_4 N1_4 C2_1 -171.3(2) . . . . ?
C2_4 C1_4 N1_4 C5_4 61.9(4) . . . . ?
C3_1 C2_1 N1_4 C1_4 -77.1(4) . . . . ?
C1_1 C2_1 N1_4 C1_4 170.6(3) . . . . ?
C3_1 C2_1 N1_4 C5_4 48.8(4) . . . . ?
C1_1 C2_1 N1_4 C5_4 -63.6(3) . . . . ?
N1_4 C1_4 C2_4 C3_4 -57.5(3) . . . . ?
C1_4 C2_4 C3_4 C4_4 53.1(4) . . . . ?
C2_4 C3_4 C4_4 C5_4 -52.5(4) . . . . ?
C1_4 N1_4 C5_4 C4_4 -61.8(3) . . . . ?
C2_1 N1_4 C5_4 C4_4 171.5(2) . . . . ?
C3_4 C4_4 C5_4 N1_4 56.9(3) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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 2103235'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H25 N3'
_chemical_formula_sum            'C18 H25 N3'
_chemical_formula_weight         283.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.071(3)
_cell_length_b                   13.890(5)
_cell_length_c                   9.126(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.97(3)
_cell_angle_gamma                90
_cell_volume                     765.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4239
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.59


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Oxford Cryostream 700).
;
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4806
_exptl_absorpt_correction_T_max  0.6942
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            7615
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.681
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        26.000
_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 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2958
_reflns_number_gt                2866
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.958

_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_refine_special_details          
;

Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.

The absolute configuration could not be reliably determined due to the fact that
only Mo radiation was available and the structure contains only C, H and N atoms.
The Flack parameter is therefore meaningless.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.1286P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
N001 N -0.0227(3) 0.61830(12) 0.43953(17) 0.0159(3) Uani 1 1 d . . . . .
N002 N 0.2166(3) 0.66620(12) 0.64204(18) 0.0168(4) Uani 1 1 d . . . . .
N003 N 0.4091(3) 0.46963(12) 0.57041(17) 0.0145(4) Uani 1 1 d . . . . .
C004 C 0.1688(3) 0.61391(14) 0.5186(2) 0.0148(4) Uani 1 1 d . . . . .
C005 C 0.3372(3) 0.54425(14) 0.4606(2) 0.0143(4) Uani 1 1 d . . . . .
H005 H 0.469240 0.581410 0.435378 0.017 Uiso 1 1 calc R U . . .
C006 C -0.1272(3) 0.48093(15) 0.0882(2) 0.0186(4) Uani 1 1 d . . . . .
H006 H -0.239066 0.468706 0.009677 0.022 Uiso 1 1 calc R U . . .
C007 C -0.0068(3) 0.55765(14) 0.3169(2) 0.0161(4) Uani 1 1 d . . . . .
C008 C 0.5907(3) 0.41178(15) 0.5226(2) 0.0170(4) Uani 1 1 d . . . . .
H00A H 0.711934 0.454803 0.498702 0.020 Uiso 1 1 calc R U . . .
H00B H 0.537164 0.375624 0.432361 0.020 Uiso 1 1 calc R U . . .
C009 C 0.2252(3) 0.40970(14) 0.6094(2) 0.0155(4) Uani 1 1 d . . . . .
H00C H 0.161269 0.373753 0.521422 0.019 Uiso 1 1 calc R U . . .
H00D H 0.107854 0.451322 0.642825 0.019 Uiso 1 1 calc R U . . .
C00A C 0.0440(3) 0.72415(15) 0.7006(2) 0.0182(4) Uani 1 1 d . . . . .
H00E H -0.093647 0.721623 0.632311 0.022 Uiso 1 1 calc R U . . .
H00F H 0.092437 0.792115 0.710345 0.022 Uiso 1 1 calc R U . . .
C00B C 0.4918(3) 0.27709(14) 0.6848(2) 0.0180(4) Uani 1 1 d . . . . .
H00G H 0.436503 0.236522 0.599664 0.022 Uiso 1 1 calc R U . . .
H00H H 0.547828 0.234115 0.766906 0.022 Uiso 1 1 calc R U . . .
C00C C 0.2009(3) 0.51274(14) 0.3192(2) 0.0159(4) Uani 1 1 d . . . . .
C00D C 0.2463(4) 0.45389(14) 0.2028(2) 0.0175(4) Uani 1 1 d . . . . .
H00I H 0.388024 0.425077 0.201549 0.021 Uiso 1 1 calc R U . . .
C00E C 0.0800(4) 0.43787(14) 0.0877(2) 0.0196(4) Uani 1 1 d . . . . .
H00J H 0.108559 0.397176 0.008167 0.024 Uiso 1 1 calc R U . . .
C00F C 0.3951(3) 0.62682(16) 0.8879(2) 0.0193(4) Uani 1 1 d . . . . .
H00K H 0.535895 0.632774 0.952529 0.023 Uiso 1 1 calc R U . . .
H00L H 0.354853 0.557767 0.881529 0.023 Uiso 1 1 calc R U . . .
C00G C 0.4279(3) 0.66434(15) 0.7343(2) 0.0169(4) Uani 1 1 d . . . . .
H00M H 0.491180 0.730048 0.741967 0.020 Uiso 1 1 calc R U . . .
H00N H 0.533309 0.622234 0.688664 0.020 Uiso 1 1 calc R U . . .
C00H C 0.0002(3) 0.68470(15) 0.8512(2) 0.0191(4) Uani 1 1 d . . . . .
H00O H -0.110685 0.725643 0.893592 0.023 Uiso 1 1 calc R U . . .
H00P H -0.060989 0.618758 0.839643 0.023 Uiso 1 1 calc R U . . .
C00I C -0.1722(3) 0.54192(15) 0.2033(2) 0.0181(4) Uani 1 1 d . . . . .
H00Q H -0.312850 0.571852 0.203431 0.022 Uiso 1 1 calc R U . . .
C00J C 0.6784(3) 0.34138(15) 0.6430(2) 0.0183(4) Uani 1 1 d . . . . .
H00R H 0.796718 0.301252 0.607474 0.022 Uiso 1 1 calc R U . . .
H00S H 0.742725 0.377524 0.730689 0.022 Uiso 1 1 calc R U . . .
C00K C 0.2134(4) 0.68265(15) 0.9557(2) 0.0202(4) Uani 1 1 d . . . . .
H00T H 0.184313 0.651981 1.049669 0.024 Uiso 1 1 calc R U . . .
H00U H 0.264099 0.749377 0.977315 0.024 Uiso 1 1 calc R U . . .
C00L C 0.3042(3) 0.33893(14) 0.7313(2) 0.0177(4) Uani 1 1 d . . . . .
H00V H 0.356131 0.374792 0.822134 0.021 Uiso 1 1 calc R U . . .
H00W H 0.179512 0.297155 0.753025 0.021 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
N001 C004 1.304(3) . ?
N001 C007 1.412(2) . ?
N002 C004 1.346(2) . ?
N002 C00G 1.459(3) . ?
N002 C00A 1.466(2) . ?
N003 C009 1.466(2) . ?
N003 C008 1.467(2) . ?
N003 C005 1.476(3) . ?
C004 C005 1.541(3) . ?
C005 C00C 1.523(3) . ?
C005 H005 1.0000 . ?
C006 C00E 1.394(3) . ?
C006 C00I 1.398(3) . ?
C006 H006 0.9500 . ?
C007 C00I 1.384(3) . ?
C007 C00C 1.405(3) . ?
C008 C00J 1.525(3) . ?
C008 H00A 0.9900 . ?
C008 H00B 0.9900 . ?
C009 C00L 1.524(3) . ?
C009 H00C 0.9900 . ?
C009 H00D 0.9900 . ?
C00A C00H 1.528(3) . ?
C00A H00E 0.9900 . ?
C00A H00F 0.9900 . ?
C00B C00L 1.522(3) . ?
C00B C00J 1.522(3) . ?
C00B H00G 0.9900 . ?
C00B H00H 0.9900 . ?
C00C C00D 1.391(3) . ?
C00D C00E 1.397(3) . ?
C00D H00I 0.9500 . ?
C00E H00J 0.9500 . ?
C00F C00G 1.528(3) . ?
C00F C00K 1.530(3) . ?
C00F H00K 0.9900 . ?
C00F H00L 0.9900 . ?
C00G H00M 0.9900 . ?
C00G H00N 0.9900 . ?
C00H C00K 1.526(3) . ?
C00H H00O 0.9900 . ?
C00H H00P 0.9900 . ?
C00I H00Q 0.9500 . ?
C00J H00R 0.9900 . ?
C00J H00S 0.9900 . ?
C00K H00T 0.9900 . ?
C00K H00U 0.9900 . ?
C00L H00V 0.9900 . ?
C00L H00W 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
C004 N001 C007 106.29(16) . . ?
C004 N002 C00G 124.97(17) . . ?
C004 N002 C00A 120.09(17) . . ?
C00G N002 C00A 114.72(15) . . ?
C009 N003 C008 112.08(15) . . ?
C009 N003 C005 112.64(15) . . ?
C008 N003 C005 111.17(14) . . ?
N001 C004 N002 122.69(17) . . ?
N001 C004 C005 115.09(16) . . ?
N002 C004 C005 122.22(17) . . ?
N003 C005 C00C 118.01(17) . . ?
N003 C005 C004 111.57(14) . . ?
C00C C005 C004 98.62(15) . . ?
N003 C005 H005 109.4 . . ?
C00C C005 H005 109.4 . . ?
C004 C005 H005 109.4 . . ?
C00E C006 C00I 120.63(19) . . ?
C00E C006 H006 119.7 . . ?
C00I C006 H006 119.7 . . ?
C00I C007 C00C 121.40(18) . . ?
C00I C007 N001 125.76(19) . . ?
C00C C007 N001 112.83(17) . . ?
N003 C008 C00J 110.73(15) . . ?
N003 C008 H00A 109.5 . . ?
C00J C008 H00A 109.5 . . ?
N003 C008 H00B 109.5 . . ?
C00J C008 H00B 109.5 . . ?
H00A C008 H00B 108.1 . . ?
N003 C009 C00L 110.72(16) . . ?
N003 C009 H00C 109.5 . . ?
C00L C009 H00C 109.5 . . ?
N003 C009 H00D 109.5 . . ?
C00L C009 H00D 109.5 . . ?
H00C C009 H00D 108.1 . . ?
N002 C00A C00H 109.21(16) . . ?
N002 C00A H00E 109.8 . . ?
C00H C00A H00E 109.8 . . ?
N002 C00A H00F 109.8 . . ?
C00H C00A H00F 109.8 . . ?
H00E C00A H00F 108.3 . . ?
C00L C00B C00J 109.69(16) . . ?
C00L C00B H00G 109.7 . . ?
C00J C00B H00G 109.7 . . ?
C00L C00B H00H 109.7 . . ?
C00J C00B H00H 109.7 . . ?
H00G C00B H00H 108.2 . . ?
C00D C00C C007 119.90(18) . . ?
C00D C00C C005 133.05(19) . . ?
C007 C00C C005 107.04(17) . . ?
C00C C00D C00E 118.87(19) . . ?
C00C C00D H00I 120.6 . . ?
C00E C00D H00I 120.6 . . ?
C006 C00E C00D 120.74(19) . . ?
C006 C00E H00J 119.6 . . ?
C00D C00E H00J 119.6 . . ?
C00G C00F C00K 111.47(17) . . ?
C00G C00F H00K 109.3 . . ?
C00K C00F H00K 109.3 . . ?
C00G C00F H00L 109.3 . . ?
C00K C00F H00L 109.3 . . ?
H00K C00F H00L 108.0 . . ?
N002 C00G C00F 110.16(16) . . ?
N002 C00G H00M 109.6 . . ?
C00F C00G H00M 109.6 . . ?
N002 C00G H00N 109.6 . . ?
C00F C00G H00N 109.6 . . ?
H00M C00G H00N 108.1 . . ?
C00K C00H C00A 110.66(17) . . ?
C00K C00H H00O 109.5 . . ?
C00A C00H H00O 109.5 . . ?
C00K C00H H00P 109.5 . . ?
C00A C00H H00P 109.5 . . ?
H00O C00H H00P 108.1 . . ?
C007 C00I C006 118.41(19) . . ?
C007 C00I H00Q 120.8 . . ?
C006 C00I H00Q 120.8 . . ?
C00B C00J C008 110.10(17) . . ?
C00B C00J H00R 109.6 . . ?
C008 C00J H00R 109.6 . . ?
C00B C00J H00S 109.6 . . ?
C008 C00J H00S 109.6 . . ?
H00R C00J H00S 108.2 . . ?
C00H C00K C00F 110.94(16) . . ?
C00H C00K H00T 109.5 . . ?
C00F C00K H00T 109.5 . . ?
C00H C00K H00U 109.5 . . ?
C00F C00K H00U 109.5 . . ?
H00T C00K H00U 108.0 . . ?
C00B C00L C009 110.39(16) . . ?
C00B C00L H00V 109.6 . . ?
C009 C00L H00V 109.6 . . ?
C00B C00L H00W 109.6 . . ?
C009 C00L H00W 109.6 . . ?
H00V C00L H00W 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
C007 N001 C004 N002 177.29(17) . . . . ?
C007 N001 C004 C005 -2.7(2) . . . . ?
C00G N002 C004 N001 -179.79(18) . . . . ?
C00A N002 C004 N001 6.0(3) . . . . ?
C00G N002 C004 C005 0.2(3) . . . . ?
C00A N002 C004 C005 -173.96(17) . . . . ?
C009 N003 C005 C00C -52.2(2) . . . . ?
C008 N003 C005 C00C 74.5(2) . . . . ?
C009 N003 C005 C004 60.9(2) . . . . ?
C008 N003 C005 C004 -172.37(15) . . . . ?
N001 C004 C005 N003 -121.20(18) . . . . ?
N002 C004 C005 N003 58.8(2) . . . . ?
N001 C004 C005 C00C 3.6(2) . . . . ?
N002 C004 C005 C00C -176.42(17) . . . . ?
C004 N001 C007 C00I -179.10(19) . . . . ?
C004 N001 C007 C00C 0.6(2) . . . . ?
C009 N003 C008 C00J -58.4(2) . . . . ?
C005 N003 C008 C00J 174.58(16) . . . . ?
C008 N003 C009 C00L 58.07(19) . . . . ?
C005 N003 C009 C00L -175.67(15) . . . . ?
C004 N002 C00A C00H 115.46(19) . . . . ?
C00G N002 C00A C00H -59.3(2) . . . . ?
C00I C007 C00C C00D 2.5(3) . . . . ?
N001 C007 C00C C00D -177.22(16) . . . . ?
C00I C007 C00C C005 -178.57(17) . . . . ?
N001 C007 C00C C005 1.8(2) . . . . ?
N003 C005 C00C C00D -64.0(3) . . . . ?
C004 C005 C00C C00D 175.9(2) . . . . ?
N003 C005 C00C C007 117.21(18) . . . . ?
C004 C005 C00C C007 -2.91(18) . . . . ?
C007 C00C C00D C00E -2.3(3) . . . . ?
C005 C00C C00D C00E 179.03(19) . . . . ?
C00I C006 C00E C00D 0.7(3) . . . . ?
C00C C00D C00E C006 0.8(3) . . . . ?
C004 N002 C00G C00F -117.0(2) . . . . ?
C00A N002 C00G C00F 57.5(2) . . . . ?
C00K C00F C00G N002 -52.7(2) . . . . ?
N002 C00A C00H C00K 56.3(2) . . . . ?
C00C C007 C00I C006 -1.0(3) . . . . ?
N001 C007 C00I C006 178.67(17) . . . . ?
C00E C006 C00I C007 -0.6(3) . . . . ?
C00L C00B C00J C008 -56.2(2) . . . . ?
N003 C008 C00J C00B 57.1(2) . . . . ?
C00A C00H C00K C00F -54.5(2) . . . . ?
C00G C00F C00K C00H 52.7(2) . . . . ?
C00J C00B C00L C009 56.0(2) . . . . ?
N003 C009 C00L C00B -56.7(2) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2103233'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 F N3'
_chemical_formula_sum            'C18 H24 F N3'
_chemical_formula_weight         301.40

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.3289(19)
_cell_length_b                   11.536(4)
_cell_length_c                   11.603(4)
_cell_angle_alpha                108.626(9)
_cell_angle_beta                 102.536(7)
_cell_angle_gamma                92.226(7)
_cell_volume                     778.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2759
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.79


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Oxford Cryostream 700).
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.159
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_T_max  0.7454
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 4.00 0.00 0.1000
0.00 -3.00 2.50 0.0750
0.00 -1.00 1.00 0.0850
0.00 -2.00 2.50 0.0950
0.00 0.00 -0.50 0.0710
0.00 -1.00 -1.00 0.0600
0.00 1.00 0.50 0.0810
0.00 -1.00 -0.50 0.0570
0.00 2.00 0.50 0.0780
0.00 1.00 0.00 0.0830
0.00 -1.00 0.00 0.0610
1.00 -4.00 3.00 0.0810
-1.00 4.00 -3.00 0.0700
1.00 -3.00 2.50 0.0840
-1.00 3.00 -2.50 0.0600
1.00 -4.00 2.50 0.0800
1.00 0.00 1.00 0.0720
-1.00 0.00 -1.00 0.0550
-1.00 -1.00 -0.50 0.0610
2.00 -5.00 3.00 0.0730
-2.00 5.00 -3.00 0.0770
1.00 2.00 0.00 0.0730
-1.00 4.00 -2.00 0.0940
1.00 -4.00 2.00 0.0870
2.00 -4.00 2.50 0.0700
1.00 0.00 0.50 0.0700
2.00 1.00 -0.50 0.0710
2.00 -1.00 -0.50 0.0770
-3.00 5.00 -0.50 0.1120
3.00 -4.00 0.00 0.0820
3.00 0.00 -2.00 0.0750
2.00 -1.00 -1.50 0.0850
-1.00 0.00 1.50 0.0760
1.00 0.00 -1.50 0.1040

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            8609
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.095
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3053
_reflns_number_gt                2270
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.3314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3053
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_1 N 0.7094(3) 0.87856(14) 0.41122(15) 0.0155(4) Uani 1 1 d . . . . .
F1_1 F 0.6465(2) 0.88292(11) 0.87748(11) 0.0288(3) Uani 1 1 d . . . . .
C2_1 C 0.3549(3) 0.80254(17) 0.41803(17) 0.0144(4) Uani 1 1 d . . . . .
H2_1 H 0.235663 0.857023 0.420742 0.017 Uiso 1 1 calc R U . . .
C3_1 C 0.5113(3) 0.84041(16) 0.54689(18) 0.0150(4) Uani 1 1 d . . . . .
C4_1 C 0.4860(3) 0.84119(17) 0.66262(18) 0.0182(4) Uani 1 1 d . . . . .
H4_1 H 0.349348 0.815414 0.673319 0.022 Uiso 1 1 calc R U . . .
C5_1 C 0.6675(3) 0.88092(18) 0.76181(18) 0.0193(4) Uani 1 1 d . . . . .
C6_1 C 0.8696(3) 0.92075(18) 0.75210(19) 0.0192(4) Uani 1 1 d . . . . .
H6_1 H 0.989931 0.946925 0.823246 0.023 Uiso 1 1 calc R U . . .
C7_1 C 0.8932(3) 0.92170(17) 0.63556(18) 0.0177(4) Uani 1 1 d . . . . .
H7_1 H 1.029559 0.949222 0.625811 0.021 Uiso 1 1 calc R U . . .
C8_1 C 0.7131(3) 0.88154(16) 0.53426(18) 0.0150(4) Uani 1 1 d . . . . .
C1_1 C 0.5094(3) 0.83650(16) 0.34478(17) 0.0137(4) Uani 1 1 d . . . . .
N1_2 N 0.4455(3) 0.82208(15) 0.22235(15) 0.0160(4) Uani 1 1 d . . . . .
C2_2 C 0.6252(3) 0.71724(19) 0.05846(19) 0.0194(4) Uani 1 1 d . . . . .
H2A_2 H 0.685684 0.660868 0.102709 0.023 Uiso 1 1 calc R U . . .
H2AB_2 H 0.726581 0.730219 0.008468 0.023 Uiso 1 1 calc R U . . .
C3_2 C 0.4030(3) 0.6589(2) -0.02869(19) 0.0214(5) Uani 1 1 d . . . . .
H3A_2 H 0.416560 0.575491 -0.083961 0.026 Uiso 1 1 calc R U . . .
H3AB_2 H 0.353357 0.708991 -0.082378 0.026 Uiso 1 1 calc R U . . .
C4_2 C 0.2337(3) 0.64958(19) 0.04501(19) 0.0198(4) Uani 1 1 d . . . . .
H4A_2 H 0.088186 0.621284 -0.013570 0.024 Uiso 1 1 calc R U . . .
H4AB_2 H 0.269585 0.587866 0.086893 0.024 Uiso 1 1 calc R U . . .
C5_2 C 0.2271(3) 0.77289(18) 0.14279(18) 0.0172(4) Uani 1 1 d . . . . .
H5A_2 H 0.170158 0.831535 0.100672 0.021 Uiso 1 1 calc R U . . .
H5AB_2 H 0.128039 0.762469 0.194998 0.021 Uiso 1 1 calc R U . . .
C1_2 C 0.6062(3) 0.83983(19) 0.15384(18) 0.0187(4) Uani 1 1 d . . . . .
H1A_2 H 0.749542 0.873691 0.213264 0.022 Uiso 1 1 calc R U . . .
H1AB_2 H 0.560563 0.899324 0.110500 0.022 Uiso 1 1 calc R U . . .
N2_3 N 0.2592(2) 0.67334(14) 0.35931(15) 0.0137(4) Uani 1 1 d . . . . .
C3_3 C 0.1236(3) 0.41939(18) 0.32378(19) 0.0184(4) Uani 1 1 d . . . . .
H3A_3 H 0.173248 0.409941 0.406947 0.022 Uiso 1 1 calc R U . . .
H3AB_3 H 0.048179 0.339158 0.263610 0.022 Uiso 1 1 calc R U . . .
C4_3 C -0.0337(3) 0.51654(18) 0.33160(19) 0.0178(4) Uani 1 1 d . . . . .
H4A_3 H -0.100566 0.516631 0.246175 0.021 Uiso 1 1 calc R U . . .
H4AB_3 H -0.151819 0.495822 0.367874 0.021 Uiso 1 1 calc R U . . .
C5_3 C 0.0819(3) 0.64390(18) 0.41183(18) 0.0161(4) Uani 1 1 d . . . . .
H5A_3 H -0.022613 0.705757 0.413713 0.019 Uiso 1 1 calc R U . . .
H5AB_3 H 0.141346 0.645916 0.498815 0.019 Uiso 1 1 calc R U . . .
C2_3 C 0.3194(3) 0.45645(17) 0.28154(19) 0.0175(4) Uani 1 1 d . . . . .
H2A_3 H 0.272896 0.451395 0.192740 0.021 Uiso 1 1 calc R U . . .
H2AB_3 H 0.429058 0.398408 0.287612 0.021 Uiso 1 1 calc R U . . .
C1_3 C 0.4218(3) 0.58687(17) 0.36166(19) 0.0164(4) Uani 1 1 d . . . . .
H1A_3 H 0.481587 0.590236 0.449050 0.020 Uiso 1 1 calc R U . . .
H1AB_3 H 0.543320 0.610519 0.329411 0.020 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_1 C1_1 1.312(2) . ?
N1_1 C8_1 1.412(2) . ?
F1_1 C5_1 1.370(2) . ?
C2_1 N2_3 1.468(2) . ?
C2_1 C3_1 1.521(3) . ?
C2_1 C1_1 1.541(2) . ?
C2_1 H2_1 1.0000 . ?
C3_1 C4_1 1.384(3) . ?
C3_1 C8_1 1.399(3) . ?
C4_1 C5_1 1.379(3) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.382(3) . ?
C6_1 C7_1 1.396(3) . ?
C6_1 H6_1 0.9500 . ?
C7_1 C8_1 1.387(3) . ?
C7_1 H7_1 0.9500 . ?
C1_1 N1_2 1.343(2) . ?
N1_2 C5_2 1.461(2) . ?
N1_2 C1_2 1.465(2) . ?
C2_2 C1_2 1.520(3) . ?
C2_2 C3_2 1.526(3) . ?
C2_2 H2A_2 0.9900 . ?
C2_2 H2AB_2 0.9900 . ?
C3_2 C4_2 1.529(3) . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3AB_2 0.9900 . ?
C4_2 C5_2 1.519(3) . ?
C4_2 H4A_2 0.9900 . ?
C4_2 H4AB_2 0.9900 . ?
C5_2 H5A_2 0.9900 . ?
C5_2 H5AB_2 0.9900 . ?
C1_2 H1A_2 0.9900 . ?
C1_2 H1AB_2 0.9900 . ?
N2_3 C1_3 1.463(2) . ?
N2_3 C5_3 1.465(2) . ?
C3_3 C2_3 1.521(3) . ?
C3_3 C4_3 1.522(3) . ?
C3_3 H3A_3 0.9900 . ?
C3_3 H3AB_3 0.9900 . ?
C4_3 C5_3 1.519(3) . ?
C4_3 H4A_3 0.9900 . ?
C4_3 H4AB_3 0.9900 . ?
C5_3 H5A_3 0.9900 . ?
C5_3 H5AB_3 0.9900 . ?
C2_3 C1_3 1.522(3) . ?
C2_3 H2A_3 0.9900 . ?
C2_3 H2AB_3 0.9900 . ?
C1_3 H1A_3 0.9900 . ?
C1_3 H1AB_3 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
C1_1 N1_1 C8_1 106.25(15) . . ?
N2_3 C2_1 C3_1 118.12(14) . . ?
N2_3 C2_1 C1_1 111.19(15) . . ?
C3_1 C2_1 C1_1 99.00(15) . . ?
N2_3 C2_1 H2_1 109.3 . . ?
C3_1 C2_1 H2_1 109.3 . . ?
C1_1 C2_1 H2_1 109.3 . . ?
C4_1 C3_1 C8_1 120.24(18) . . ?
C4_1 C3_1 C2_1 132.72(18) . . ?
C8_1 C3_1 C2_1 107.04(16) . . ?
C5_1 C4_1 C3_1 117.25(19) . . ?
C5_1 C4_1 H4_1 121.4 . . ?
C3_1 C4_1 H4_1 121.4 . . ?
F1_1 C5_1 C4_1 118.35(18) . . ?
F1_1 C5_1 C6_1 117.75(18) . . ?
C4_1 C5_1 C6_1 123.89(18) . . ?
C5_1 C6_1 C7_1 118.59(18) . . ?
C5_1 C6_1 H6_1 120.7 . . ?
C7_1 C6_1 H6_1 120.7 . . ?
C8_1 C7_1 C6_1 118.53(19) . . ?
C8_1 C7_1 H7_1 120.7 . . ?
C6_1 C7_1 H7_1 120.7 . . ?
C7_1 C8_1 C3_1 121.48(17) . . ?
C7_1 C8_1 N1_1 125.40(17) . . ?
C3_1 C8_1 N1_1 113.11(16) . . ?
N1_1 C1_1 N1_2 122.71(16) . . ?
N1_1 C1_1 C2_1 114.55(16) . . ?
N1_2 C1_1 C2_1 122.73(16) . . ?
C1_1 N1_2 C5_2 125.25(15) . . ?
C1_1 N1_2 C1_2 120.16(15) . . ?
C5_2 N1_2 C1_2 114.06(15) . . ?
C1_2 C2_2 C3_2 110.75(16) . . ?
C1_2 C2_2 H2A_2 109.5 . . ?
C3_2 C2_2 H2A_2 109.5 . . ?
C1_2 C2_2 H2AB_2 109.5 . . ?
C3_2 C2_2 H2AB_2 109.5 . . ?
H2A_2 C2_2 H2AB_2 108.1 . . ?
C2_2 C3_2 C4_2 111.51(16) . . ?
C2_2 C3_2 H3A_2 109.3 . . ?
C4_2 C3_2 H3A_2 109.3 . . ?
C2_2 C3_2 H3AB_2 109.3 . . ?
C4_2 C3_2 H3AB_2 109.3 . . ?
H3A_2 C3_2 H3AB_2 108.0 . . ?
C5_2 C4_2 C3_2 111.29(16) . . ?
C5_2 C4_2 H4A_2 109.4 . . ?
C3_2 C4_2 H4A_2 109.4 . . ?
C5_2 C4_2 H4AB_2 109.4 . . ?
C3_2 C4_2 H4AB_2 109.4 . . ?
H4A_2 C4_2 H4AB_2 108.0 . . ?
N1_2 C5_2 C4_2 110.14(15) . . ?
N1_2 C5_2 H5A_2 109.6 . . ?
C4_2 C5_2 H5A_2 109.6 . . ?
N1_2 C5_2 H5AB_2 109.6 . . ?
C4_2 C5_2 H5AB_2 109.6 . . ?
H5A_2 C5_2 H5AB_2 108.1 . . ?
N1_2 C1_2 C2_2 109.57(15) . . ?
N1_2 C1_2 H1A_2 109.8 . . ?
C2_2 C1_2 H1A_2 109.8 . . ?
N1_2 C1_2 H1AB_2 109.8 . . ?
C2_2 C1_2 H1AB_2 109.8 . . ?
H1A_2 C1_2 H1AB_2 108.2 . . ?
C1_3 N2_3 C5_3 110.82(14) . . ?
C1_3 N2_3 C2_1 112.82(15) . . ?
C5_3 N2_3 C2_1 112.65(15) . . ?
C2_3 C3_3 C4_3 110.31(15) . . ?
C2_3 C3_3 H3A_3 109.6 . . ?
C4_3 C3_3 H3A_3 109.6 . . ?
C2_3 C3_3 H3AB_3 109.6 . . ?
C4_3 C3_3 H3AB_3 109.6 . . ?
H3A_3 C3_3 H3AB_3 108.1 . . ?
C5_3 C4_3 C3_3 111.27(16) . . ?
C5_3 C4_3 H4A_3 109.4 . . ?
C3_3 C4_3 H4A_3 109.4 . . ?
C5_3 C4_3 H4AB_3 109.4 . . ?
C3_3 C4_3 H4AB_3 109.4 . . ?
H4A_3 C4_3 H4AB_3 108.0 . . ?
N2_3 C5_3 C4_3 109.26(15) . . ?
N2_3 C5_3 H5A_3 109.8 . . ?
C4_3 C5_3 H5A_3 109.8 . . ?
N2_3 C5_3 H5AB_3 109.8 . . ?
C4_3 C5_3 H5AB_3 109.8 . . ?
H5A_3 C5_3 H5AB_3 108.3 . . ?
C3_3 C2_3 C1_3 111.13(16) . . ?
C3_3 C2_3 H2A_3 109.4 . . ?
C1_3 C2_3 H2A_3 109.4 . . ?
C3_3 C2_3 H2AB_3 109.4 . . ?
C1_3 C2_3 H2AB_3 109.4 . . ?
H2A_3 C2_3 H2AB_3 108.0 . . ?
N2_3 C1_3 C2_3 110.29(16) . . ?
N2_3 C1_3 H1A_3 109.6 . . ?
C2_3 C1_3 H1A_3 109.6 . . ?
N2_3 C1_3 H1AB_3 109.6 . . ?
C2_3 C1_3 H1AB_3 109.6 . . ?
H1A_3 C1_3 H1AB_3 108.1 . . ?

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
N2_3 C2_1 C3_1 C4_1 -62.7(3) . . . . ?
C1_1 C2_1 C3_1 C4_1 177.3(2) . . . . ?
N2_3 C2_1 C3_1 C8_1 117.87(17) . . . . ?
C1_1 C2_1 C3_1 C8_1 -2.10(17) . . . . ?
C8_1 C3_1 C4_1 C5_1 -1.5(3) . . . . ?
C2_1 C3_1 C4_1 C5_1 179.17(18) . . . . ?
C3_1 C4_1 C5_1 F1_1 179.79(16) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.8(3) . . . . ?
F1_1 C5_1 C6_1 C7_1 -178.75(16) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.3(3) . . . . ?
C5_1 C6_1 C7_1 C8_1 -0.6(3) . . . . ?
C6_1 C7_1 C8_1 C3_1 -0.2(3) . . . . ?
C6_1 C7_1 C8_1 N1_1 179.02(17) . . . . ?
C4_1 C3_1 C8_1 C7_1 1.3(3) . . . . ?
C2_1 C3_1 C8_1 C7_1 -179.26(16) . . . . ?
C4_1 C3_1 C8_1 N1_1 -178.03(16) . . . . ?
C2_1 C3_1 C8_1 N1_1 1.5(2) . . . . ?
C1_1 N1_1 C8_1 C7_1 -179.18(18) . . . . ?
C1_1 N1_1 C8_1 C3_1 0.1(2) . . . . ?
C8_1 N1_1 C1_1 N1_2 179.54(17) . . . . ?
C8_1 N1_1 C1_1 C2_1 -1.6(2) . . . . ?
N2_3 C2_1 C1_1 N1_1 -122.60(17) . . . . ?
C3_1 C2_1 C1_1 N1_1 2.37(19) . . . . ?
N2_3 C2_1 C1_1 N1_2 56.2(2) . . . . ?
C3_1 C2_1 C1_1 N1_2 -178.80(16) . . . . ?
N1_1 C1_1 N1_2 C5_2 178.37(17) . . . . ?
C2_1 C1_1 N1_2 C5_2 -0.4(3) . . . . ?
N1_1 C1_1 N1_2 C1_2 7.1(3) . . . . ?
C2_1 C1_1 N1_2 C1_2 -171.59(16) . . . . ?
C1_2 C2_2 C3_2 C4_2 -53.1(2) . . . . ?
C2_2 C3_2 C4_2 C5_2 52.0(2) . . . . ?
C1_1 N1_2 C5_2 C4_2 -113.0(2) . . . . ?
C1_2 N1_2 C5_2 C4_2 58.7(2) . . . . ?
C3_2 C4_2 C5_2 N1_2 -53.3(2) . . . . ?
C1_1 N1_2 C1_2 C2_2 112.38(19) . . . . ?
C5_2 N1_2 C1_2 C2_2 -59.8(2) . . . . ?
C3_2 C2_2 C1_2 N1_2 55.5(2) . . . . ?
C3_1 C2_1 N2_3 C1_3 -49.1(2) . . . . ?
C1_1 C2_1 N2_3 C1_3 64.30(19) . . . . ?
C3_1 C2_1 N2_3 C5_3 77.3(2) . . . . ?
C1_1 C2_1 N2_3 C5_3 -169.29(14) . . . . ?
C2_3 C3_3 C4_3 C5_3 -53.0(2) . . . . ?
C1_3 N2_3 C5_3 C4_3 -62.45(19) . . . . ?
C2_1 N2_3 C5_3 C4_3 170.08(14) . . . . ?
C3_3 C4_3 C5_3 N2_3 57.98(19) . . . . ?
C4_3 C3_3 C2_3 C1_3 51.7(2) . . . . ?
C5_3 N2_3 C1_3 C2_3 61.8(2) . . . . ?
C2_1 N2_3 C1_3 C2_3 -170.82(14) . . . . ?
C3_3 C2_3 C1_3 N2_3 -56.07(19) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2103234'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H27 N3'
_chemical_formula_sum            'C19 H27 N3'
_chemical_formula_weight         297.43

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'

_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                   5.617(3)
_cell_length_b                   9.249(4)
_cell_length_c                   32.279(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.18(2)
_cell_angle_gamma                90
_cell_volume                     1672.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    993
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      21.50


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
glass fiber and transferred to stream of cold nitrogen.
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5157
_exptl_absorpt_correction_T_max  0.7456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0290
0.00 0.00 1.00 0.0670
0.00 -1.00 3.00 0.0350
0.00 1.00 -3.00 0.0480
0.00 2.00 -3.00 0.0680
0.00 -3.00 -1.00 0.0170
0.00 3.00 2.00 0.0890
0.00 -2.00 -3.00 0.0110
0.00 2.00 3.00 0.0970
0.00 -1.00 -2.00 0.0090
-1.00 3.00 -3.00 0.0660
1.00 -3.00 3.00 0.0340
1.00 -2.00 3.00 0.0410
-1.00 3.00 1.00 0.0800
-1.00 1.00 -2.00 0.0580
1.00 -1.00 1.00 0.0650
-1.00 1.00 -1.00 0.0640
-2.00 1.00 -3.00 0.0540
2.00 -1.00 3.00 0.0840
-2.00 -1.00 3.00 0.0620
2.00 1.00 -3.00 0.1110

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex1)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            16192
_diffrn_reflns_av_unetI/netI     0.1452
_diffrn_reflns_av_R_equivalents  0.1300
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.265
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3289
_reflns_number_gt                2077
_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       'Smart NT ver. 5.63 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3289
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_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
C1_1 C 0.5831(4) 0.3585(3) 0.38481(7) 0.0223(5) Uani 1 1 d . . . . .
N1_1 N 0.6508(3) 0.3911(2) 0.34435(6) 0.0229(5) Uani 1 1 d . . . . .
C2_1 C 0.3956(4) 0.2676(3) 0.39389(7) 0.0240(5) Uani 1 1 d . . . . .
C3_1 C 0.3604(4) 0.2484(3) 0.43611(7) 0.0264(6) Uani 1 1 d . . . . .
H3_1 H 0.234386 0.187428 0.443611 0.032 Uiso 1 1 calc R U . . .
C4_1 C 0.5032(4) 0.3152(3) 0.46722(7) 0.0277(6) Uani 1 1 d . . . . .
H00H_1 H 0.473442 0.299266 0.495457 0.033 Uiso 1 1 calc R U . . .
C5_1 C 0.6899(4) 0.4055(3) 0.45768(7) 0.0270(6) Uani 1 1 d . . . . .
H5_1 H 0.789529 0.450407 0.478984 0.032 Uiso 1 1 calc R U . . .
C6_1 C 0.7258(4) 0.4280(3) 0.41610(7) 0.0225(5) Uani 1 1 d . . . . .
C7_1 C 0.9049(4) 0.5201(3) 0.39485(7) 0.0216(5) Uani 1 1 d . . . . .
H7_1 H 1.068760 0.480700 0.401836 0.026 Uiso 1 1 calc R U . . .
C8_1 C 0.8283(4) 0.4828(3) 0.34949(7) 0.0228(5) Uani 1 1 d . . . . .
C9_1 C 0.2391(4) 0.1959(3) 0.36014(8) 0.0308(6) Uani 1 1 d . . . . .
H00K_1 H 0.173917 0.269262 0.340559 0.046 Uiso 1 1 calc R U . . .
H00L_1 H 0.107853 0.145562 0.372434 0.046 Uiso 1 1 calc R U . . .
H00M_1 H 0.333569 0.126123 0.345422 0.046 Uiso 1 1 calc R U . . .
N1_2 N 0.9081(3) 0.6773(2) 0.40222(6) 0.0218(5) Uani 1 1 d . . . . .
C2_2 C 1.0491(4) 0.8785(3) 0.44674(8) 0.0286(6) Uani 1 1 d . . . . .
H00N_2 H 1.165034 0.909939 0.426886 0.034 Uiso 1 1 calc R U . . .
H00O_2 H 1.115228 0.903485 0.475106 0.034 Uiso 1 1 calc R U . . .
C3_2 C 0.8129(4) 0.9576(3) 0.43735(8) 0.0325(6) Uani 1 1 d . . . . .
H00X_2 H 0.704305 0.936936 0.459440 0.039 Uiso 1 1 calc R U . . .
H00Y_2 H 0.841386 1.063134 0.436792 0.039 Uiso 1 1 calc R U . . .
C4_2 C 0.6980(4) 0.9086(3) 0.39566(8) 0.0302(6) Uani 1 1 d . . . . .
H00T_2 H 0.796534 0.941594 0.373266 0.036 Uiso 1 1 calc R U . . .
H00U_2 H 0.538264 0.953457 0.391010 0.036 Uiso 1 1 calc R U . . .
C5_2 C 0.6733(4) 0.7451(3) 0.39377(7) 0.0247(6) Uani 1 1 d . . . . .
H5_2 H 0.563847 0.712375 0.414557 0.030 Uiso 1 1 calc R U . . .
H00C_2 H 0.604651 0.715895 0.365910 0.030 Uiso 1 1 calc R U . . .
C1_2 C 1.0142(4) 0.7157(3) 0.44346(7) 0.0251(6) Uani 1 1 d . . . . .
H00D_2 H 1.170132 0.666512 0.448528 0.030 Uiso 1 1 calc R U . . .
H00E_2 H 0.908681 0.682928 0.464857 0.030 Uiso 1 1 calc R U . . .
N1_3 N 0.9346(3) 0.5428(2) 0.31722(5) 0.0236(5) Uani 1 1 d . . . . .
C2_3 C 1.1732(4) 0.7454(3) 0.29354(7) 0.0318(6) Uani 1 1 d . . . . .
H00P_3 H 1.334057 0.789690 0.296242 0.038 Uiso 1 1 calc R U . . .
H00Q_3 H 1.056443 0.819064 0.301226 0.038 Uiso 1 1 calc R U . . .
C3_3 C 1.1150(4) 0.6987(3) 0.24880(8) 0.0337(7) Uani 1 1 d . . . . .
H00R_3 H 1.241851 0.633547 0.240020 0.040 Uiso 1 1 calc R U . . .
H00S_3 H 1.108927 0.784569 0.230463 0.040 Uiso 1 1 calc R U . . .
C4_3 C 0.8752(4) 0.6205(3) 0.24461(7) 0.0328(6) Uani 1 1 d . . . . .
H00V_3 H 0.746284 0.689886 0.249673 0.039 Uiso 1 1 calc R U . . .
H00W_3 H 0.846452 0.583448 0.215902 0.039 Uiso 1 1 calc R U . . .
C5_3 C 0.8668(4) 0.4955(3) 0.27495(7) 0.0273(6) Uani 1 1 d . . . . .
H00I_3 H 0.703286 0.454910 0.273616 0.033 Uiso 1 1 calc R U . . .
H00J_3 H 0.976787 0.418306 0.267024 0.033 Uiso 1 1 calc R U . . .
C1_3 C 1.1661(4) 0.6171(3) 0.32286(7) 0.0265(6) Uani 1 1 d . . . . .
H00F_3 H 1.295733 0.548720 0.317374 0.032 Uiso 1 1 calc R U . . .
H00G_3 H 1.192446 0.650961 0.351926 0.032 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
C1_1 C2_1 1.396(3) . ?
C1_1 C6_1 1.399(3) . ?
C1_1 N1_1 1.419(3) . ?
N1_1 C8_1 1.310(3) . ?
C2_1 C3_1 1.402(3) . ?
C2_1 C9_1 1.503(3) . ?
C3_1 C4_1 1.384(3) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.393(3) . ?
C4_1 H00H_1 0.9500 . ?
C5_1 C6_1 1.387(3) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.519(3) . ?
C7_1 N1_2 1.473(3) . ?
C7_1 C8_1 1.535(3) . ?
C7_1 H7_1 1.0000 . ?
C8_1 N1_3 1.357(3) . ?
C9_1 H00K_1 0.9800 . ?
C9_1 H00L_1 0.9800 . ?
C9_1 H00M_1 0.9800 . ?
N1_2 C1_2 1.462(3) . ?
N1_2 C5_2 1.468(3) . ?
C2_2 C1_2 1.521(3) . ?
C2_2 C3_2 1.526(3) . ?
C2_2 H00N_2 0.9900 . ?
C2_2 H00O_2 0.9900 . ?
C3_2 C4_2 1.518(3) . ?
C3_2 H00X_2 0.9900 . ?
C3_2 H00Y_2 0.9900 . ?
C4_2 C5_2 1.519(4) . ?
C4_2 H00T_2 0.9900 . ?
C4_2 H00U_2 0.9900 . ?
C5_2 H5_2 0.9900 . ?
C5_2 H00C_2 0.9900 . ?
C1_2 H00D_2 0.9900 . ?
C1_2 H00E_2 0.9900 . ?
N1_3 C5_3 1.457(3) . ?
N1_3 C1_3 1.470(3) . ?
C2_3 C1_3 1.520(3) . ?
C2_3 C3_3 1.520(4) . ?
C2_3 H00P_3 0.9900 . ?
C2_3 H00Q_3 0.9900 . ?
C3_3 C4_3 1.526(3) . ?
C3_3 H00R_3 0.9900 . ?
C3_3 H00S_3 0.9900 . ?
C4_3 C5_3 1.518(4) . ?
C4_3 H00V_3 0.9900 . ?
C4_3 H00W_3 0.9900 . ?
C5_3 H00I_3 0.9900 . ?
C5_3 H00J_3 0.9900 . ?
C1_3 H00F_3 0.9900 . ?
C1_3 H00G_3 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_1 C1_1 C6_1 121.8(2) . . ?
C2_1 C1_1 N1_1 125.3(2) . . ?
C6_1 C1_1 N1_1 112.9(2) . . ?
C8_1 N1_1 C1_1 105.87(19) . . ?
C1_1 C2_1 C3_1 116.2(2) . . ?
C1_1 C2_1 C9_1 121.6(2) . . ?
C3_1 C2_1 C9_1 122.2(2) . . ?
C4_1 C3_1 C2_1 122.2(2) . . ?
C4_1 C3_1 H3_1 118.9 . . ?
C2_1 C3_1 H3_1 118.9 . . ?
C3_1 C4_1 C5_1 120.9(2) . . ?
C3_1 C4_1 H00H_1 119.6 . . ?
C5_1 C4_1 H00H_1 119.6 . . ?
C6_1 C5_1 C4_1 118.0(2) . . ?
C6_1 C5_1 H5_1 121.0 . . ?
C4_1 C5_1 H5_1 121.0 . . ?
C5_1 C6_1 C1_1 120.9(2) . . ?
C5_1 C6_1 C7_1 132.0(2) . . ?
C1_1 C6_1 C7_1 107.16(19) . . ?
N1_2 C7_1 C6_1 118.75(17) . . ?
N1_2 C7_1 C8_1 112.00(19) . . ?
C6_1 C7_1 C8_1 98.98(18) . . ?
N1_2 C7_1 H7_1 108.8 . . ?
C6_1 C7_1 H7_1 108.8 . . ?
C8_1 C7_1 H7_1 108.8 . . ?
N1_1 C8_1 N1_3 122.8(2) . . ?
N1_1 C8_1 C7_1 115.08(19) . . ?
N1_3 C8_1 C7_1 122.1(2) . . ?
C2_1 C9_1 H00K_1 109.5 . . ?
C2_1 C9_1 H00L_1 109.5 . . ?
H00K_1 C9_1 H00L_1 109.5 . . ?
C2_1 C9_1 H00M_1 109.5 . . ?
H00K_1 C9_1 H00M_1 109.5 . . ?
H00L_1 C9_1 H00M_1 109.5 . . ?
C1_2 N1_2 C5_2 111.48(17) . . ?
C1_2 N1_2 C7_1 112.72(18) . . ?
C5_2 N1_2 C7_1 113.07(18) . . ?
C1_2 C2_2 C3_2 110.8(2) . . ?
C1_2 C2_2 H00N_2 109.5 . . ?
C3_2 C2_2 H00N_2 109.5 . . ?
C1_2 C2_2 H00O_2 109.5 . . ?
C3_2 C2_2 H00O_2 109.5 . . ?
H00N_2 C2_2 H00O_2 108.1 . . ?
C4_2 C3_2 C2_2 109.9(2) . . ?
C4_2 C3_2 H00X_2 109.7 . . ?
C2_2 C3_2 H00X_2 109.7 . . ?
C4_2 C3_2 H00Y_2 109.7 . . ?
C2_2 C3_2 H00Y_2 109.7 . . ?
H00X_2 C3_2 H00Y_2 108.2 . . ?
C3_2 C4_2 C5_2 111.3(2) . . ?
C3_2 C4_2 H00T_2 109.4 . . ?
C5_2 C4_2 H00T_2 109.4 . . ?
C3_2 C4_2 H00U_2 109.4 . . ?
C5_2 C4_2 H00U_2 109.4 . . ?
H00T_2 C4_2 H00U_2 108.0 . . ?
N1_2 C5_2 C4_2 109.86(18) . . ?
N1_2 C5_2 H5_2 109.7 . . ?
C4_2 C5_2 H5_2 109.7 . . ?
N1_2 C5_2 H00C_2 109.7 . . ?
C4_2 C5_2 H00C_2 109.7 . . ?
H5_2 C5_2 H00C_2 108.2 . . ?
N1_2 C1_2 C2_2 110.25(19) . . ?
N1_2 C1_2 H00D_2 109.6 . . ?
C2_2 C1_2 H00D_2 109.6 . . ?
N1_2 C1_2 H00E_2 109.6 . . ?
C2_2 C1_2 H00E_2 109.6 . . ?
H00D_2 C1_2 H00E_2 108.1 . . ?
C8_1 N1_3 C5_3 119.8(2) . . ?
C8_1 N1_3 C1_3 122.09(19) . . ?
C5_3 N1_3 C1_3 115.14(17) . . ?
C1_3 C2_3 C3_3 110.9(2) . . ?
C1_3 C2_3 H00P_3 109.5 . . ?
C3_3 C2_3 H00P_3 109.5 . . ?
C1_3 C2_3 H00Q_3 109.5 . . ?
C3_3 C2_3 H00Q_3 109.5 . . ?
H00P_3 C2_3 H00Q_3 108.1 . . ?
C2_3 C3_3 C4_3 110.27(19) . . ?
C2_3 C3_3 H00R_3 109.6 . . ?
C4_3 C3_3 H00R_3 109.6 . . ?
C2_3 C3_3 H00S_3 109.6 . . ?
C4_3 C3_3 H00S_3 109.6 . . ?
H00R_3 C3_3 H00S_3 108.1 . . ?
C5_3 C4_3 C3_3 111.9(2) . . ?
C5_3 C4_3 H00V_3 109.2 . . ?
C3_3 C4_3 H00V_3 109.2 . . ?
C5_3 C4_3 H00W_3 109.2 . . ?
C3_3 C4_3 H00W_3 109.2 . . ?
H00V_3 C4_3 H00W_3 107.9 . . ?
N1_3 C5_3 C4_3 110.9(2) . . ?
N1_3 C5_3 H00I_3 109.5 . . ?
C4_3 C5_3 H00I_3 109.5 . . ?
N1_3 C5_3 H00J_3 109.5 . . ?
C4_3 C5_3 H00J_3 109.5 . . ?
H00I_3 C5_3 H00J_3 108.0 . . ?
N1_3 C1_3 C2_3 110.53(19) . . ?
N1_3 C1_3 H00F_3 109.5 . . ?
C2_3 C1_3 H00F_3 109.5 . . ?
N1_3 C1_3 H00G_3 109.5 . . ?
C2_3 C1_3 H00G_3 109.5 . . ?
H00F_3 C1_3 H00G_3 108.1 . . ?

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
C2_1 C1_1 N1_1 C8_1 178.2(2) . . . . ?
C6_1 C1_1 N1_1 C8_1 -1.8(3) . . . . ?
C6_1 C1_1 C2_1 C3_1 -0.8(3) . . . . ?
N1_1 C1_1 C2_1 C3_1 179.2(2) . . . . ?
C6_1 C1_1 C2_1 C9_1 178.6(2) . . . . ?
N1_1 C1_1 C2_1 C9_1 -1.4(4) . . . . ?
C1_1 C2_1 C3_1 C4_1 -0.1(3) . . . . ?
C9_1 C2_1 C3_1 C4_1 -179.5(2) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.1(4) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.9(4) . . . . ?
C4_1 C5_1 C6_1 C1_1 -1.8(3) . . . . ?
C4_1 C5_1 C6_1 C7_1 178.6(2) . . . . ?
C2_1 C1_1 C6_1 C5_1 1.8(3) . . . . ?
N1_1 C1_1 C6_1 C5_1 -178.2(2) . . . . ?
C2_1 C1_1 C6_1 C7_1 -178.5(2) . . . . ?
N1_1 C1_1 C6_1 C7_1 1.5(3) . . . . ?
C5_1 C6_1 C7_1 N1_2 -59.7(3) . . . . ?
C1_1 C6_1 C7_1 N1_2 120.7(2) . . . . ?
C5_1 C6_1 C7_1 C8_1 179.0(2) . . . . ?
C1_1 C6_1 C7_1 C8_1 -0.6(2) . . . . ?
C1_1 N1_1 C8_1 N1_3 -177.5(2) . . . . ?
C1_1 N1_1 C8_1 C7_1 1.4(3) . . . . ?
N1_2 C7_1 C8_1 N1_1 -126.6(2) . . . . ?
C6_1 C7_1 C8_1 N1_1 -0.5(2) . . . . ?
N1_2 C7_1 C8_1 N1_3 52.3(3) . . . . ?
C6_1 C7_1 C8_1 N1_3 178.4(2) . . . . ?
C6_1 C7_1 N1_2 C1_2 74.1(2) . . . . ?
C8_1 C7_1 N1_2 C1_2 -171.44(16) . . . . ?
C6_1 C7_1 N1_2 C5_2 -53.4(3) . . . . ?
C8_1 C7_1 N1_2 C5_2 61.0(2) . . . . ?
C1_2 C2_2 C3_2 C4_2 -53.6(3) . . . . ?
C2_2 C3_2 C4_2 C5_2 53.8(2) . . . . ?
C1_2 N1_2 C5_2 C4_2 60.3(2) . . . . ?
C7_1 N1_2 C5_2 C4_2 -171.43(17) . . . . ?
C3_2 C4_2 C5_2 N1_2 -56.9(2) . . . . ?
C5_2 N1_2 C1_2 C2_2 -60.7(2) . . . . ?
C7_1 N1_2 C1_2 C2_2 170.90(17) . . . . ?
C3_2 C2_2 C1_2 N1_2 57.0(2) . . . . ?
N1_1 C8_1 N1_3 C5_3 -5.7(3) . . . . ?
C7_1 C8_1 N1_3 C5_3 175.4(2) . . . . ?
N1_1 C8_1 N1_3 C1_3 -165.1(2) . . . . ?
C7_1 C8_1 N1_3 C1_3 16.0(3) . . . . ?
C1_3 C2_3 C3_3 C4_3 55.2(3) . . . . ?
C2_3 C3_3 C4_3 C5_3 -54.1(3) . . . . ?
C8_1 N1_3 C5_3 C4_3 145.2(2) . . . . ?
C1_3 N1_3 C5_3 C4_3 -54.0(3) . . . . ?
C3_3 C4_3 C5_3 N1_3 52.5(3) . . . . ?
C8_1 N1_3 C1_3 C2_3 -144.3(2) . . . . ?
C5_3 N1_3 C1_3 C2_3 55.5(3) . . . . ?
C3_3 C2_3 C1_3 N1_3 -55.0(2) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 2103236'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2.21 H2.84 N0.42 O0.21'
_chemical_formula_sum            'C2.21 H2.84 N0.42 O0.21'
_chemical_formula_weight         38.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.3974(18)
_cell_length_b                   12.354(4)
_cell_length_c                   12.818(4)
_cell_angle_alpha                105.132(12)
_cell_angle_beta                 102.567(9)
_cell_angle_gamma                91.995(10)
_cell_volume                     950.0(5)
_cell_formula_units_Z            19
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    8516
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      26.10


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             394
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6207
_exptl_absorpt_correction_T_max  0.7453
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3.00 -1.00 1.00 0.1500
0.00 -3.00 2.00 0.0490
0.00 3.00 -2.00 0.0720
0.00 1.00 1.00 0.0960
3.00 0.00 -2.00 0.1480
0.00 1.00 3.00 0.0790
0.00 -1.00 -3.00 0.0670
0.00 -2.00 -3.00 0.0570
-1.00 -2.00 1.00 0.1160
-3.00 3.00 -1.00 0.1670

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      175(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon II)'
_diffrn_detector_area_resol_mean 7.5
_diffrn_reflns_number            13120
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.278
_diffrn_reflns_theta_max         26.145
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3745
_reflns_number_gt                3072
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.3850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3745
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4663(2) 0.18405(10) 0.12190(12) 0.0478(3) Uani 1 1 d . . . . .
C1 C 0.5362(2) 0.37500(13) 0.14433(13) 0.0307(3) Uani 1 1 d . . . . .
N1 N 0.4125(2) 0.27955(12) 0.15491(12) 0.0378(3) Uani 1 1 d . . . . .
N2 N 0.56847(18) 0.76025(10) 0.29751(10) 0.0271(3) Uani 1 1 d . . . . .
C2 C 0.7206(3) 0.35649(13) 0.10398(13) 0.0326(3) Uani 1 1 d . . . . .
H2 H 0.765486 0.282782 0.085767 0.039 Uiso 1 1 calc R U . . .
N3 N 0.8621(2) 0.65097(10) 0.10532(10) 0.0288(3) Uani 1 1 d . . . . .
C3 C 0.8389(2) 0.44610(13) 0.09040(13) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.964869 0.434732 0.062596 0.038 Uiso 1 1 calc R U . . .
N4 N 0.7798(2) 0.83739(11) 0.13577(11) 0.0309(3) Uani 1 1 d . . . . .
C4 C 0.7689(2) 0.55271(13) 0.11840(12) 0.0275(3) Uani 1 1 d . . . . .
O005 O 0.2552(2) 0.29697(12) 0.19529(15) 0.0637(4) Uani 1 1 d . . . . .
C5 C 0.5839(2) 0.57004(12) 0.16149(12) 0.0271(3) Uani 1 1 d . . . . .
C7 C 0.7416(2) 0.73145(12) 0.13808(12) 0.0269(3) Uani 1 1 d . . . . .
C6 C 0.4641(2) 0.48170(13) 0.17383(12) 0.0299(3) Uani 1 1 d . . . . .
H6 H 0.337654 0.492705 0.201236 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5544(2) 0.69413(12) 0.18297(12) 0.0261(3) Uani 1 1 d . . . . .
H8 H 0.414825 0.703837 0.134737 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7647(2) 0.74756(15) 0.37532(13) 0.0346(4) Uani 1 1 d . . . . .
H00E H 0.891459 0.759075 0.345470 0.042 Uiso 1 1 calc R U . . .
H00F H 0.758819 0.670391 0.384290 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7865(3) 0.83307(16) 0.48748(14) 0.0414(4) Uani 1 1 d . . . . .
H00O H 0.803332 0.910183 0.479301 0.050 Uiso 1 1 calc R U . . .
H00P H 0.916705 0.822329 0.540399 0.050 Uiso 1 1 calc R U . . .
C11 C 0.5892(3) 0.81972(17) 0.53310(14) 0.0436(4) Uani 1 1 d . . . . .
H00Q H 0.584528 0.747009 0.551888 0.052 Uiso 1 1 calc R U . . .
H00R H 0.598795 0.880989 0.601955 0.052 Uiso 1 1 calc R U . . .
C12 C 0.3854(3) 0.82346(17) 0.44810(14) 0.0422(4) Uani 1 1 d . . . . .
H00K H 0.379978 0.900131 0.437927 0.051 Uiso 1 1 calc R U . . .
H00L H 0.258461 0.806611 0.475711 0.051 Uiso 1 1 calc R U . . .
C13 C 0.3772(2) 0.73856(14) 0.33698(13) 0.0341(4) Uani 1 1 d . . . . .
H00A H 0.370803 0.661241 0.345550 0.041 Uiso 1 1 calc R U . . .
H00D H 0.246279 0.744546 0.281896 0.041 Uiso 1 1 calc R U . . .
C14 C 0.9625(2) 0.87240(14) 0.09555(14) 0.0343(4) Uani 1 1 d . . . . .
H14 H 0.908892 0.886428 0.022211 0.041 Uiso 1 1 calc R U . . .
H00J H 1.058635 0.811286 0.086180 0.041 Uiso 1 1 calc R U . . .
C15 C 1.0877(2) 0.97873(14) 0.17723(15) 0.0368(4) Uani 1 1 d . . . . .
H00U H 1.200078 1.005609 0.145097 0.044 Uiso 1 1 calc R U . . .
H00V H 1.160211 0.961272 0.246608 0.044 Uiso 1 1 calc R U . . .
C16 C 0.9416(3) 1.07133(14) 0.20426(15) 0.0377(4) Uani 1 1 d . . . . .
H00S H 0.882925 1.095762 0.136907 0.045 Uiso 1 1 calc R U . . .
H00T H 1.025501 1.137107 0.262087 0.045 Uiso 1 1 calc R U . . .
C17 C 0.7570(3) 1.02888(14) 0.24566(14) 0.0359(4) Uani 1 1 d . . . . .
H00M H 0.814768 1.011134 0.316825 0.043 Uiso 1 1 calc R U . . .
H00N H 0.658531 1.088390 0.259106 0.043 Uiso 1 1 calc R U . . .
C18 C 0.6343(2) 0.92437(13) 0.16049(14) 0.0331(4) Uani 1 1 d . . . . .
H00G H 0.519161 0.895374 0.189564 0.040 Uiso 1 1 calc R U . . .
H18 H 0.565939 0.943657 0.091443 0.040 Uiso 1 1 calc R U . . .
C21 C 0.1801(4) 0.5704(2) 0.5558(2) 0.0702(7) Uani 1 1 d . . . . .
H00X H 0.306347 0.619611 0.594426 0.084 Uiso 1 1 calc R U . . .
C20 C -0.0051(4) 0.4246(2) 0.40051(19) 0.0683(6) Uani 1 1 d . . . . .
H00W H -0.008730 0.372182 0.331007 0.082 Uiso 1 1 calc R U . . .
C19 C 0.1754(4) 0.4946(2) 0.4561(2) 0.0707(7) Uani 1 1 d . . . . .
H00Y H 0.298685 0.490892 0.425695 0.085 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
O1 N1 1.2331(18) . ?
C1 C2 1.391(2) . ?
C1 C6 1.397(2) . ?
C1 N1 1.450(2) . ?
N1 O005 1.2290(19) . ?
N2 C13 1.4634(18) . ?
N2 C8 1.4637(18) . ?
N2 C9 1.465(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
N3 C7 1.3176(19) . ?
N3 C4 1.399(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
N4 C7 1.332(2) . ?
N4 C18 1.4637(19) . ?
N4 C14 1.4703(18) . ?
C4 C5 1.412(2) . ?
C5 C6 1.374(2) . ?
C5 C8 1.511(2) . ?
C7 C8 1.5415(19) . ?
C6 H6 0.9500 . ?
C8 H8 1.0000 . ?
C9 C10 1.520(2) . ?
C9 H00E 0.9900 . ?
C9 H00F 0.9900 . ?
C10 C11 1.523(2) . ?
C10 H00O 0.9900 . ?
C10 H00P 0.9900 . ?
C11 C12 1.517(3) . ?
C11 H00Q 0.9900 . ?
C11 H00R 0.9900 . ?
C12 C13 1.522(2) . ?
C12 H00K 0.9900 . ?
C12 H00L 0.9900 . ?
C13 H00A 0.9900 . ?
C13 H00D 0.9900 . ?
C14 C15 1.519(2) . ?
C14 H14 0.9900 . ?
C14 H00J 0.9900 . ?
C15 C16 1.520(2) . ?
C15 H00U 0.9900 . ?
C15 H00V 0.9900 . ?
C16 C17 1.525(2) . ?
C16 H00S 0.9900 . ?
C16 H00T 0.9900 . ?
C17 C18 1.515(2) . ?
C17 H00M 0.9900 . ?
C17 H00N 0.9900 . ?
C18 H00G 0.9900 . ?
C18 H18 0.9900 . ?
C21 C20 1.353(3) 2_566 ?
C21 C19 1.366(4) . ?
C21 H00X 0.9500 . ?
C20 C19 1.356(4) . ?
C20 H00W 0.9500 . ?
C19 H00Y 0.9500 . ?

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 C1 C6 122.63(14) . . ?
C2 C1 N1 118.68(14) . . ?
C6 C1 N1 118.68(14) . . ?
O005 N1 O1 122.38(14) . . ?
O005 N1 C1 118.44(14) . . ?
O1 N1 C1 119.17(14) . . ?
C13 N2 C8 112.66(11) . . ?
C13 N2 C9 110.94(12) . . ?
C8 N2 C9 113.09(11) . . ?
C3 C2 C1 119.79(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C7 N3 C4 106.28(12) . . ?
C4 C3 C2 118.47(14) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C7 N4 C18 123.62(12) . . ?
C7 N4 C14 121.55(12) . . ?
C18 N4 C14 114.50(12) . . ?
C3 C4 N3 126.10(13) . . ?
C3 C4 C5 120.82(14) . . ?
N3 C4 C5 113.05(13) . . ?
C6 C5 C4 121.14(14) . . ?
C6 C5 C8 131.79(13) . . ?
C4 C5 C8 107.04(12) . . ?
N3 C7 N4 123.29(13) . . ?
N3 C7 C8 114.51(13) . . ?
N4 C7 C8 122.17(12) . . ?
C5 C6 C1 117.12(14) . . ?
C5 C6 H6 121.4 . . ?
C1 C6 H6 121.4 . . ?
N2 C8 C5 118.29(12) . . ?
N2 C8 C7 111.35(11) . . ?
C5 C8 C7 98.98(11) . . ?
N2 C8 H8 109.2 . . ?
C5 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
N2 C9 C10 109.93(13) . . ?
N2 C9 H00E 109.7 . . ?
C10 C9 H00E 109.7 . . ?
N2 C9 H00F 109.7 . . ?
C10 C9 H00F 109.7 . . ?
H00E C9 H00F 108.2 . . ?
C9 C10 C11 110.60(14) . . ?
C9 C10 H00O 109.5 . . ?
C11 C10 H00O 109.5 . . ?
C9 C10 H00P 109.5 . . ?
C11 C10 H00P 109.5 . . ?
H00O C10 H00P 108.1 . . ?
C12 C11 C10 110.48(15) . . ?
C12 C11 H00Q 109.6 . . ?
C10 C11 H00Q 109.6 . . ?
C12 C11 H00R 109.6 . . ?
C10 C11 H00R 109.6 . . ?
H00Q C11 H00R 108.1 . . ?
C11 C12 C13 110.98(14) . . ?
C11 C12 H00K 109.4 . . ?
C13 C12 H00K 109.4 . . ?
C11 C12 H00L 109.4 . . ?
C13 C12 H00L 109.4 . . ?
H00K C12 H00L 108.0 . . ?
N2 C13 C12 109.82(13) . . ?
N2 C13 H00A 109.7 . . ?
C12 C13 H00A 109.7 . . ?
N2 C13 H00D 109.7 . . ?
C12 C13 H00D 109.7 . . ?
H00A C13 H00D 108.2 . . ?
N4 C14 C15 110.49(13) . . ?
N4 C14 H14 109.6 . . ?
C15 C14 H14 109.6 . . ?
N4 C14 H00J 109.6 . . ?
C15 C14 H00J 109.6 . . ?
H14 C14 H00J 108.1 . . ?
C14 C15 C16 111.55(13) . . ?
C14 C15 H00U 109.3 . . ?
C16 C15 H00U 109.3 . . ?
C14 C15 H00V 109.3 . . ?
C16 C15 H00V 109.3 . . ?
H00U C15 H00V 108.0 . . ?
C15 C16 C17 110.29(13) . . ?
C15 C16 H00S 109.6 . . ?
C17 C16 H00S 109.6 . . ?
C15 C16 H00T 109.6 . . ?
C17 C16 H00T 109.6 . . ?
H00S C16 H00T 108.1 . . ?
C18 C17 C16 110.17(13) . . ?
C18 C17 H00M 109.6 . . ?
C16 C17 H00M 109.6 . . ?
C18 C17 H00N 109.6 . . ?
C16 C17 H00N 109.6 . . ?
H00M C17 H00N 108.1 . . ?
N4 C18 C17 110.29(13) . . ?
N4 C18 H00G 109.6 . . ?
C17 C18 H00G 109.6 . . ?
N4 C18 H18 109.6 . . ?
C17 C18 H18 109.6 . . ?
H00G C18 H18 108.1 . . ?
C20 C21 C19 120.1(2) 2_566 . ?
C20 C21 H00X 119.9 2_566 . ?
C19 C21 H00X 119.9 . . ?
C21 C20 C19 119.9(2) 2_566 . ?
C21 C20 H00W 120.1 2_566 . ?
C19 C20 H00W 120.1 . . ?
C20 C19 C21 120.0(2) . . ?
C20 C19 H00Y 120.0 . . ?
C21 C19 H00Y 120.0 . . ?

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
C2 C1 N1 O005 176.76(16) . . . . ?
C6 C1 N1 O005 -4.0(2) . . . . ?
C2 C1 N1 O1 -4.2(2) . . . . ?
C6 C1 N1 O1 175.01(15) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
N1 C1 C2 C3 178.37(14) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 N3 -176.85(14) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C7 N3 C4 C3 177.66(15) . . . . ?
C7 N3 C4 C5 -0.41(17) . . . . ?
C3 C4 C5 C6 -2.0(2) . . . . ?
N3 C4 C5 C6 176.19(13) . . . . ?
C3 C4 C5 C8 179.83(13) . . . . ?
N3 C4 C5 C8 -1.99(17) . . . . ?
C4 N3 C7 N4 -178.96(14) . . . . ?
C4 N3 C7 C8 2.71(17) . . . . ?
C18 N4 C7 N3 173.13(14) . . . . ?
C14 N4 C7 N3 0.1(2) . . . . ?
C18 N4 C7 C8 -8.7(2) . . . . ?
C14 N4 C7 C8 178.30(13) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C8 C5 C6 C1 179.09(15) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
N1 C1 C6 C5 -179.24(13) . . . . ?
C13 N2 C8 C5 -74.82(16) . . . . ?
C9 N2 C8 C5 51.99(17) . . . . ?
C13 N2 C8 C7 171.56(12) . . . . ?
C9 N2 C8 C7 -61.63(16) . . . . ?
C6 C5 C8 N2 65.0(2) . . . . ?
C4 C5 C8 N2 -117.12(13) . . . . ?
C6 C5 C8 C7 -174.80(16) . . . . ?
C4 C5 C8 C7 3.11(14) . . . . ?
N3 C7 C8 N2 121.53(14) . . . . ?
N4 C7 C8 N2 -56.82(18) . . . . ?
N3 C7 C8 C5 -3.71(16) . . . . ?
N4 C7 C8 C5 177.94(14) . . . . ?
C13 N2 C9 C10 -61.94(17) . . . . ?
C8 N2 C9 C10 170.34(13) . . . . ?
N2 C9 C10 C11 57.3(2) . . . . ?
C9 C10 C11 C12 -53.2(2) . . . . ?
C10 C11 C12 C13 53.1(2) . . . . ?
C8 N2 C13 C12 -170.44(13) . . . . ?
C9 N2 C13 C12 61.61(18) . . . . ?
C11 C12 C13 N2 -57.0(2) . . . . ?
C7 N4 C14 C15 -131.38(15) . . . . ?
C18 N4 C14 C15 55.00(18) . . . . ?
N4 C14 C15 C16 -52.92(18) . . . . ?
C14 C15 C16 C17 54.69(19) . . . . ?
C15 C16 C17 C18 -56.22(18) . . . . ?
C7 N4 C18 C17 129.33(15) . . . . ?
C14 N4 C18 C17 -57.20(18) . . . . ?
C16 C17 C18 N4 56.61(17) . . . . ?
C21 C20 C19 C21 -0.3(4) 2_566 . . . ?
C20 C21 C19 C20 0.3(4) 2_566 . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2103241'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H30 N4'
_chemical_formula_sum            'C20 H30 N4'
_chemical_formula_weight         326.48

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   8.002(9)
_cell_length_b                   12.763(13)
_cell_length_c                   34.89(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3563(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3041
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      21.51


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.196
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5990
_exptl_absorpt_correction_T_max  0.7454
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 -1.00 0.0960
-1.00 0.00 1.00 0.0660
1.00 0.00 -1.00 0.1120
-1.00 0.00 0.00 0.0630
-1.00 -1.00 0.00 0.0820
1.00 1.00 0.00 0.1130
1.00 1.00 -1.00 0.0980
-1.00 -1.00 1.00 0.0790
-1.00 1.00 -1.00 0.0550
1.00 -1.00 1.00 0.0960
0.00 0.00 1.00 0.1100
0.00 0.00 -1.00 0.0180
0.00 -1.00 -1.00 0.0930
0.00 1.00 1.00 0.0800

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            33618
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_av_R_equivalents  0.1444
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3623
_reflns_number_gt                2172
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.0068P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3623
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.7627(3) 0.7000(2) 0.58829(7) 0.0195(6) Uani 1 1 d . . . . .
N1 N 0.3716(3) 0.59784(17) 0.62594(6) 0.0224(5) Uani 1 1 d . . . . .
C2 C 0.7567(3) 0.5930(2) 0.57922(7) 0.0203(6) Uani 1 1 d . . . . .
N2 N 0.6084(3) 0.54314(17) 0.59213(6) 0.0214(5) Uani 1 1 d . . . . .
C3 C 0.8869(3) 0.5483(2) 0.55901(7) 0.0252(6) Uani 1 1 d . . . . .
H3 H 0.884384 0.475870 0.552703 0.030 Uiso 1 1 calc R U . . .
N3 N 0.6331(3) 0.75270(16) 0.65247(6) 0.0182(5) Uani 1 1 d . . . . .
C6 C 0.8962(3) 0.7623(2) 0.57728(7) 0.0222(6) Uani 1 1 d . . . . .
H6 H 0.897495 0.834880 0.583376 0.027 Uiso 1 1 calc R U . . .
C5 C 1.0302(3) 0.7168(2) 0.55691(7) 0.0233(6) Uani 1 1 d . . . . .
C4 C 1.0225(3) 0.6106(2) 0.54791(7) 0.0256(7) Uani 1 1 d . . . . .
H4 H 1.111490 0.579612 0.533895 0.031 Uiso 1 1 calc R U . . .
N4 N 1.1713(3) 0.77948(19) 0.54778(6) 0.0296(6) Uani 1 1 d . . . . .
C8 C 0.5223(3) 0.6161(2) 0.60964(7) 0.0208(6) Uani 1 1 d . . . . .
C7 C 0.6079(3) 0.7235(2) 0.61184(7) 0.0189(6) Uani 1 1 d . . . . .
H7 H 0.538057 0.777577 0.598653 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7481(4) 0.6803(2) 0.67191(7) 0.0221(6) Uani 1 1 d . . . . .
H9A H 0.861767 0.688524 0.661111 0.026 Uiso 1 1 calc R U . . .
H9AB H 0.711554 0.607281 0.667366 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7527(4) 0.7017(2) 0.71476(7) 0.0247(6) Uani 1 1 d . . . . .
H10A H 0.641167 0.687684 0.725942 0.030 Uiso 1 1 calc R U . . .
H10B H 0.834017 0.653987 0.727108 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8017(3) 0.8141(2) 0.72262(7) 0.0246(6) Uani 1 1 d . . . . .
H11A H 0.919808 0.825215 0.715188 0.029 Uiso 1 1 calc R U . . .
H11B H 0.791050 0.828913 0.750371 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6901(4) 0.8884(2) 0.70010(7) 0.0242(7) Uani 1 1 d . . . . .
H12A H 0.730417 0.961125 0.703441 0.029 Uiso 1 1 calc R U . . .
H12B H 0.574693 0.884438 0.710205 0.029 Uiso 1 1 calc R U . . .
C13 C 0.6896(3) 0.86078(19) 0.65757(7) 0.0220(6) Uani 1 1 d . . . . .
H13A H 0.614103 0.908942 0.643594 0.026 Uiso 1 1 calc R U . . .
H13B H 0.803536 0.868894 0.646937 0.026 Uiso 1 1 calc R U . . .
C14 C 0.2655(3) 0.6790(2) 0.64265(7) 0.0224(6) Uani 1 1 d . . . . .
H14A H 0.155614 0.679190 0.629633 0.027 Uiso 1 1 calc R U . . .
H14B H 0.317883 0.748457 0.638807 0.027 Uiso 1 1 calc R U . . .
C15 C 0.2413(4) 0.6592(2) 0.68521(7) 0.0231(6) Uani 1 1 d . . . . .
H15A H 0.349470 0.667129 0.698658 0.028 Uiso 1 1 calc R U . . .
H15B H 0.162507 0.711524 0.695808 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1732(4) 0.5497(2) 0.69194(8) 0.0264(7) Uani 1 1 d . . . . .
H16A H 0.057925 0.545237 0.681762 0.032 Uiso 1 1 calc R U . . .
H16B H 0.168801 0.535633 0.719828 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2816(4) 0.4675(2) 0.67256(7) 0.0258(7) Uani 1 1 d . . . . .
H17A H 0.228665 0.397764 0.675395 0.031 Uiso 1 1 calc R U . . .
H17B H 0.392114 0.465028 0.685268 0.031 Uiso 1 1 calc R U . . .
C18 C 0.3049(4) 0.4918(2) 0.63011(8) 0.0257(7) Uani 1 1 d . . . . .
H18A H 0.383004 0.440616 0.618537 0.031 Uiso 1 1 calc R U . . .
H18B H 0.196328 0.486222 0.616641 0.031 Uiso 1 1 calc R U . . .
C20 C 1.3076(4) 0.7262(3) 0.52833(8) 0.0381(8) Uani 1 1 d . . . . .
H20A H 1.271019 0.704499 0.502727 0.057 Uiso 1 1 calc R U . . .
H20B H 1.340561 0.664251 0.543133 0.057 Uiso 1 1 calc R U . . .
H20C H 1.403160 0.773777 0.526032 0.057 Uiso 1 1 calc R U . . .
C19 C 1.1378(4) 0.8822(2) 0.53107(8) 0.0357(8) Uani 1 1 d . . . . .
H19A H 1.238912 0.925343 0.532507 0.054 Uiso 1 1 calc R U . . .
H19B H 1.047366 0.916349 0.545279 0.054 Uiso 1 1 calc R U . . .
H19C H 1.104789 0.873739 0.504200 0.054 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
C1 C6 1.387(4) . ?
C1 C2 1.403(4) . ?
C1 C7 1.516(4) . ?
N1 C8 1.353(4) . ?
N1 C14 1.460(3) . ?
N1 C18 1.463(3) . ?
C2 C3 1.381(4) . ?
C2 N2 1.420(3) . ?
N2 C8 1.310(3) . ?
C3 C4 1.400(4) . ?
C3 H3 0.9500 . ?
N3 C13 1.462(3) . ?
N3 C9 1.469(3) . ?
N3 C7 1.479(3) . ?
C6 C5 1.411(4) . ?
C6 H6 0.9500 . ?
C5 C4 1.394(4) . ?
C5 N4 1.420(4) . ?
C4 H4 0.9500 . ?
N4 C20 1.454(4) . ?
N4 C19 1.459(4) . ?
C8 C7 1.535(4) . ?
C7 H7 1.0000 . ?
C9 C10 1.520(4) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.521(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.525(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.518(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.520(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C6 C1 C2 121.5(2) . . ?
C6 C1 C7 131.8(2) . . ?
C2 C1 C7 106.7(2) . . ?
C8 N1 C14 124.3(2) . . ?
C8 N1 C18 121.8(2) . . ?
C14 N1 C18 113.9(2) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 N2 127.4(2) . . ?
C1 C2 N2 113.1(2) . . ?
C8 N2 C2 105.6(2) . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C13 N3 C9 110.1(2) . . ?
C13 N3 C7 113.3(2) . . ?
C9 N3 C7 111.7(2) . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 N4 122.2(2) . . ?
C6 C5 N4 119.0(3) . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C5 N4 C20 116.0(2) . . ?
C5 N4 C19 116.7(2) . . ?
C20 N4 C19 111.8(2) . . ?
N2 C8 N1 122.8(3) . . ?
N2 C8 C7 115.1(2) . . ?
N1 C8 C7 122.0(2) . . ?
N3 C7 C1 117.2(2) . . ?
N3 C7 C8 109.5(2) . . ?
C1 C7 C8 99.2(2) . . ?
N3 C7 H7 110.1 . . ?
C1 C7 H7 110.1 . . ?
C8 C7 H7 110.1 . . ?
N3 C9 C10 110.9(2) . . ?
N3 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N3 C9 H9AB 109.5 . . ?
C10 C9 H9AB 109.5 . . ?
H9A C9 H9AB 108.1 . . ?
C11 C10 C9 110.8(2) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 110.2(2) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 111.1(2) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N3 C13 C12 109.7(2) . . ?
N3 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N3 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N1 C14 C15 110.3(2) . . ?
N1 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
N1 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.5(2) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C17 111.2(2) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 111.2(2) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N1 C18 C17 109.2(2) . . ?
N1 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
N1 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C6 C1 C2 C3 0.3(4) . . . . ?
C7 C1 C2 C3 -177.4(2) . . . . ?
C6 C1 C2 N2 -178.5(2) . . . . ?
C7 C1 C2 N2 3.8(3) . . . . ?
C3 C2 N2 C8 -179.7(3) . . . . ?
C1 C2 N2 C8 -1.0(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
N2 C2 C3 C4 178.6(2) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C7 C1 C6 C5 176.1(2) . . . . ?
C1 C6 C5 C4 1.1(4) . . . . ?
C1 C6 C5 N4 -176.1(2) . . . . ?
C6 C5 C4 C3 -0.9(4) . . . . ?
N4 C5 C4 C3 176.3(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C4 C5 N4 C20 0.2(4) . . . . ?
C6 C5 N4 C20 177.3(2) . . . . ?
C4 C5 N4 C19 135.2(3) . . . . ?
C6 C5 N4 C19 -47.7(3) . . . . ?
C2 N2 C8 N1 -180.0(2) . . . . ?
C2 N2 C8 C7 -2.4(3) . . . . ?
C14 N1 C8 N2 -174.3(2) . . . . ?
C18 N1 C8 N2 9.1(4) . . . . ?
C14 N1 C8 C7 8.3(4) . . . . ?
C18 N1 C8 C7 -168.3(2) . . . . ?
C13 N3 C7 C1 77.2(3) . . . . ?
C9 N3 C7 C1 -47.8(3) . . . . ?
C13 N3 C7 C8 -170.8(2) . . . . ?
C9 N3 C7 C8 64.1(3) . . . . ?
C6 C1 C7 N3 -64.2(4) . . . . ?
C2 C1 C7 N3 113.1(2) . . . . ?
C6 C1 C7 C8 178.2(3) . . . . ?
C2 C1 C7 C8 -4.5(3) . . . . ?
N2 C8 C7 N3 -118.9(2) . . . . ?
N1 C8 C7 N3 58.7(3) . . . . ?
N2 C8 C7 C1 4.4(3) . . . . ?
N1 C8 C7 C1 -178.0(2) . . . . ?
C13 N3 C9 C10 61.5(3) . . . . ?
C7 N3 C9 C10 -171.7(2) . . . . ?
N3 C9 C10 C11 -57.0(3) . . . . ?
C9 C10 C11 C12 52.6(3) . . . . ?
C10 C11 C12 C13 -53.5(3) . . . . ?
C9 N3 C13 C12 -61.5(3) . . . . ?
C7 N3 C13 C12 172.6(2) . . . . ?
C11 C12 C13 N3 58.0(3) . . . . ?
C8 N1 C14 C15 -117.5(3) . . . . ?
C18 N1 C14 C15 59.3(3) . . . . ?
N1 C14 C15 C16 -55.0(3) . . . . ?
C14 C15 C16 C17 53.5(3) . . . . ?
C15 C16 C17 C18 -53.9(3) . . . . ?
C8 N1 C18 C17 118.2(3) . . . . ?
C14 N1 C18 C17 -58.8(3) . . . . ?
C16 C17 C18 N1 54.9(3) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2103239'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H30 N4'
_chemical_formula_sum            'C25 H30 N4'
_chemical_formula_weight         386.53

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'

_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                   6.249(9)
_cell_length_b                   29.67(4)
_cell_length_c                   11.62(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.92(2)
_cell_angle_gamma                90
_cell_volume                     2122(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6216
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.67


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5763
_exptl_absorpt_correction_T_max  0.7375
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0150
0.00 0.00 1.00 0.0630
0.00 -1.00 2.00 0.0450
0.00 1.00 -2.00 0.0330
1.00 1.00 0.00 0.0500
0.00 1.00 -1.00 0.0500
0.00 -1.00 1.00 0.0390
0.00 -2.00 -3.00 0.0180
1.00 -2.00 -2.00 0.0340
0.00 1.00 3.00 0.0710
0.00 -1.00 -3.00 0.0120
-3.00 2.00 10.00 0.1010
3.00 -2.00 -10.00 0.0160

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            41175
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4507
_reflns_number_gt                3474
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+0.3847P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4507
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.5079(2) 0.58492(4) 0.76461(11) 0.0154(3) Uani 1 1 d . . . . .
N1 N 0.72734(18) 0.46252(4) 0.91756(9) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.3615(2) 0.66041(4) 0.66916(11) 0.0255(3) Uani 1 1 d . . . . .
C2 C 0.3649(2) 0.54799(4) 0.76616(11) 0.0152(3) Uani 1 1 d . . . . .
H2 H 0.215184 0.550570 0.733631 0.018 Uiso 1 1 calc R U . . .
C3 C 0.4488(2) 0.50819(4) 0.81614(11) 0.0137(3) Uani 1 1 d . . . . .
C4 C 0.3465(2) 0.46221(4) 0.82952(11) 0.0138(3) Uani 1 1 d . . . . .
H4 H 0.230229 0.465042 0.878384 0.017 Uiso 1 1 calc R U . . .
C6 C 0.6705(2) 0.50481(4) 0.86736(11) 0.0136(3) Uani 1 1 d . . . . .
C5 C 0.5470(2) 0.43794(4) 0.89974(11) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.4262(2) 0.62688(5) 0.71210(12) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.7288(2) 0.58125(5) 0.81488(11) 0.0156(3) Uani 1 1 d . . . . .
H8 H 0.822425 0.606363 0.812840 0.019 Uiso 1 1 calc R U . . .
C7 C 0.8121(2) 0.54135(4) 0.86752(11) 0.0150(3) Uani 1 1 d . . . . .
H7 H 0.960715 0.538987 0.902528 0.018 Uiso 1 1 calc R U . . .
N1_1 N 0.26319(17) 0.43703(4) 0.72159(9) 0.0140(2) Uani 1 1 d . . . . .
C2_1 C -0.0410(2) 0.42368(5) 0.56029(12) 0.0211(3) Uani 1 1 d . . . . .
H2A_1 H -0.076740 0.394381 0.593130 0.025 Uiso 1 1 calc R U . . .
H2AB_1 H -0.177138 0.436836 0.517146 0.025 Uiso 1 1 calc R U . . .
C3_1 C 0.1190(2) 0.41621(5) 0.47654(12) 0.0203(3) Uani 1 1 d . . . . .
H3A_1 H 0.138345 0.444679 0.435061 0.024 Uiso 1 1 calc R U . . .
H3AB_1 H 0.060202 0.393291 0.417583 0.024 Uiso 1 1 calc R U . . .
C4_1 C 0.3388(2) 0.40039(5) 0.54348(12) 0.0196(3) Uani 1 1 d . . . . .
H4A_1 H 0.323299 0.369916 0.575751 0.024 Uiso 1 1 calc R U . . .
H4AB_1 H 0.444895 0.398573 0.489438 0.024 Uiso 1 1 calc R U . . .
C5_1 C 0.4227(2) 0.43296(5) 0.64287(11) 0.0169(3) Uani 1 1 d . . . . .
H5A_1 H 0.562270 0.421764 0.687018 0.020 Uiso 1 1 calc R U . . .
H5AB_1 H 0.448539 0.462924 0.610366 0.020 Uiso 1 1 calc R U . . .
C1_1 C 0.0559(2) 0.45532(5) 0.65958(12) 0.0178(3) Uani 1 1 d . . . . .
H1A_1 H 0.080471 0.485420 0.627462 0.021 Uiso 1 1 calc R U . . .
H1AB_1 H -0.047118 0.458784 0.714863 0.021 Uiso 1 1 calc R U . . .
N1_2 N 0.54011(18) 0.39535(4) 0.93597(10) 0.0153(3) Uani 1 1 d . . . . .
C2_2 C 0.3699(2) 0.32690(5) 0.84190(12) 0.0183(3) Uani 1 1 d . . . . .
H2A_2 H 0.376303 0.337617 0.761885 0.022 Uiso 1 1 calc R U . . .
H2AB_2 H 0.242623 0.306723 0.837655 0.022 Uiso 1 1 calc R U . . .
C3_2 C 0.5777(2) 0.30051(5) 0.88929(13) 0.0196(3) Uani 1 1 d . . . . .
H3A_2 H 0.598836 0.276495 0.833160 0.024 Uiso 1 1 calc R U . . .
H3AB_2 H 0.561883 0.285944 0.964003 0.024 Uiso 1 1 calc R U . . .
C4_2 C 0.7779(2) 0.33144(5) 0.90910(13) 0.0190(3) Uani 1 1 d . . . . .
H4A_2 H 0.906656 0.314127 0.946516 0.023 Uiso 1 1 calc R U . . .
H4AB_2 H 0.806254 0.342755 0.833011 0.023 Uiso 1 1 calc R U . . .
C5_2 C 0.7409(2) 0.37126(5) 0.98695(12) 0.0182(3) Uani 1 1 d . . . . .
H5A_2 H 0.728736 0.360224 1.065960 0.022 Uiso 1 1 calc R U . . .
H5AB_2 H 0.866134 0.392133 0.994370 0.022 Uiso 1 1 calc R U . . .
C1_2 C 0.3428(2) 0.36720(5) 0.91990(12) 0.0164(3) Uani 1 1 d . . . . .
H1A_2 H 0.216048 0.385363 0.883713 0.020 Uiso 1 1 calc R U . . .
H1AB_2 H 0.316068 0.356432 0.996788 0.020 Uiso 1 1 calc R U . . .
C2_3 C 0.0659(3) 0.73874(5) 0.79729(14) 0.0260(3) Uani 1 1 d . . . . .
H2_3 H 0.162791 0.729721 0.746957 0.031 Uiso 1 1 calc R U . . .
C1_3 C -0.1384(3) 0.71865(5) 0.78771(13) 0.0225(3) Uani 1 1 d . . . . .
H1_3 H -0.180687 0.696033 0.730435 0.027 Uiso 1 1 calc R U . . .
C3_3 C 0.1269(2) 0.77197(5) 0.88073(14) 0.0260(4) Uani 1 1 d . . . . .
H3_3 H 0.265186 0.785955 0.886783 0.031 Uiso 1 1 calc R U . . .
C4_3 C -0.0137(2) 0.78483(5) 0.95538(13) 0.0242(3) Uani 1 1 d . . . . .
H4_3 H 0.029195 0.807315 1.012959 0.029 Uiso 1 1 calc R U . . .
C5_3 C -0.2179(2) 0.76467(5) 0.94565(13) 0.0227(3) Uani 1 1 d . . . . .
H5_3 H -0.314436 0.773516 0.996370 0.027 Uiso 1 1 calc R U . . .
C6_3 C -0.2800(2) 0.73157(5) 0.86145(12) 0.0208(3) Uani 1 1 d . . . . .
H6_3 H -0.419075 0.717866 0.854535 0.025 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
C1 C8 1.408(3) . ?
C1 C2 1.416(2) . ?
C1 C9 1.441(3) . ?
N1 C5 1.328(2) . ?
N1 C6 1.403(2) . ?
N2 C9 1.154(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9500 . ?
C3 C6 1.414(3) . ?
C3 C4 1.526(3) . ?
C4 N1_1 1.476(4) . ?
C4 C5 1.550(3) . ?
C4 H4 1.0000 . ?
C6 C7 1.399(2) . ?
C5 N1_2 1.335(2) . ?
C8 C7 1.392(2) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
N1_1 C5_1 1.469(3) . ?
N1_1 C1_1 1.473(2) . ?
C2_1 C3_1 1.527(3) . ?
C2_1 C1_1 1.529(3) . ?
C2_1 H2A_1 0.9900 . ?
C2_1 H2AB_1 0.9900 . ?
C3_1 C4_1 1.531(3) . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3AB_1 0.9900 . ?
C4_1 C5_1 1.528(4) . ?
C4_1 H4A_1 0.9900 . ?
C4_1 H4AB_1 0.9900 . ?
C5_1 H5A_1 0.9900 . ?
C5_1 H5AB_1 0.9900 . ?
C1_1 H1A_1 0.9900 . ?
C1_1 H1AB_1 0.9900 . ?
N1_2 C1_2 1.474(2) . ?
N1_2 C5_2 1.476(2) . ?
C2_2 C1_2 1.527(3) . ?
C2_2 C3_2 1.535(3) . ?
C2_2 H2A_2 0.9900 . ?
C2_2 H2AB_2 0.9900 . ?
C3_2 C4_2 1.536(3) . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3AB_2 0.9900 . ?
C4_2 C5_2 1.530(3) . ?
C4_2 H4A_2 0.9900 . ?
C4_2 H4AB_2 0.9900 . ?
C5_2 H5A_2 0.9900 . ?
C5_2 H5AB_2 0.9900 . ?
C1_2 H1A_2 0.9900 . ?
C1_2 H1AB_2 0.9900 . ?
C2_3 C3_3 1.389(3) . ?
C2_3 C1_3 1.396(3) . ?
C2_3 H2_3 0.9500 . ?
C1_3 C6_3 1.388(3) . ?
C1_3 H1_3 0.9500 . ?
C3_3 C4_3 1.390(3) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.397(3) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.393(3) . ?
C5_3 H5_3 0.9500 . ?
C6_3 H6_3 0.9500 . ?

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
C8 C1 C2 120.73(14) . . ?
C8 C1 C9 119.56(13) . . ?
C2 C1 C9 119.71(15) . . ?
C5 N1 C6 106.18(14) . . ?
C3 C2 C1 118.24(15) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C6 120.77(13) . . ?
C2 C3 C4 132.32(15) . . ?
C6 C3 C4 106.90(13) . . ?
N1_1 C4 C3 117.30(17) . . ?
N1_1 C4 C5 110.33(15) . . ?
C3 C4 C5 98.87(14) . . ?
N1_1 C4 H4 109.9 . . ?
C3 C4 H4 109.9 . . ?
C5 C4 H4 109.9 . . ?
C7 C6 N1 125.25(14) . . ?
C7 C6 C3 121.28(14) . . ?
N1 C6 C3 113.45(12) . . ?
N1 C5 N1_2 122.90(13) . . ?
N1 C5 C4 114.48(15) . . ?
N1_2 C5 C4 122.59(13) . . ?
N2 C9 C1 179.39(16) . . ?
C7 C8 C1 120.94(13) . . ?
C7 C8 H8 119.5 . . ?
C1 C8 H8 119.5 . . ?
C8 C7 C6 118.02(15) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C5_1 N1_1 C1_1 111.1(2) . . ?
C5_1 N1_1 C4 113.14(19) . . ?
C1_1 N1_1 C4 112.41(14) . . ?
C3_1 C2_1 C1_1 110.62(19) . . ?
C3_1 C2_1 H2A_1 109.5 . . ?
C1_1 C2_1 H2A_1 109.5 . . ?
C3_1 C2_1 H2AB_1 109.5 . . ?
C1_1 C2_1 H2AB_1 109.5 . . ?
H2A_1 C2_1 H2AB_1 108.1 . . ?
C2_1 C3_1 C4_1 110.4(2) . . ?
C2_1 C3_1 H3A_1 109.6 . . ?
C4_1 C3_1 H3A_1 109.6 . . ?
C2_1 C3_1 H3AB_1 109.6 . . ?
C4_1 C3_1 H3AB_1 109.6 . . ?
H3A_1 C3_1 H3AB_1 108.1 . . ?
C5_1 C4_1 C3_1 110.57(15) . . ?
C5_1 C4_1 H4A_1 109.5 . . ?
C3_1 C4_1 H4A_1 109.5 . . ?
C5_1 C4_1 H4AB_1 109.5 . . ?
C3_1 C4_1 H4AB_1 109.5 . . ?
H4A_1 C4_1 H4AB_1 108.1 . . ?
N1_1 C5_1 C4_1 109.98(19) . . ?
N1_1 C5_1 H5A_1 109.7 . . ?
C4_1 C5_1 H5A_1 109.7 . . ?
N1_1 C5_1 H5AB_1 109.7 . . ?
C4_1 C5_1 H5AB_1 109.7 . . ?
H5A_1 C5_1 H5AB_1 108.2 . . ?
N1_1 C1_1 C2_1 110.10(15) . . ?
N1_1 C1_1 H1A_1 109.6 . . ?
C2_1 C1_1 H1A_1 109.6 . . ?
N1_1 C1_1 H1AB_1 109.6 . . ?
C2_1 C1_1 H1AB_1 109.6 . . ?
H1A_1 C1_1 H1AB_1 108.2 . . ?
C5 N1_2 C1_2 124.62(12) . . ?
C5 N1_2 C5_2 120.89(13) . . ?
C1_2 N1_2 C5_2 114.27(15) . . ?
C1_2 C2_2 C3_2 111.08(16) . . ?
C1_2 C2_2 H2A_2 109.4 . . ?
C3_2 C2_2 H2A_2 109.4 . . ?
C1_2 C2_2 H2AB_2 109.4 . . ?
C3_2 C2_2 H2AB_2 109.4 . . ?
H2A_2 C2_2 H2AB_2 108.0 . . ?
C2_2 C3_2 C4_2 111.45(16) . . ?
C2_2 C3_2 H3A_2 109.3 . . ?
C4_2 C3_2 H3A_2 109.3 . . ?
C2_2 C3_2 H3AB_2 109.3 . . ?
C4_2 C3_2 H3AB_2 109.3 . . ?
H3A_2 C3_2 H3AB_2 108.0 . . ?
C5_2 C4_2 C3_2 110.36(14) . . ?
C5_2 C4_2 H4A_2 109.6 . . ?
C3_2 C4_2 H4A_2 109.6 . . ?
C5_2 C4_2 H4AB_2 109.6 . . ?
C3_2 C4_2 H4AB_2 109.6 . . ?
H4A_2 C4_2 H4AB_2 108.1 . . ?
N1_2 C5_2 C4_2 109.94(17) . . ?
N1_2 C5_2 H5A_2 109.7 . . ?
C4_2 C5_2 H5A_2 109.7 . . ?
N1_2 C5_2 H5AB_2 109.7 . . ?
C4_2 C5_2 H5AB_2 109.7 . . ?
H5A_2 C5_2 H5AB_2 108.2 . . ?
N1_2 C1_2 C2_2 110.05(13) . . ?
N1_2 C1_2 H1A_2 109.7 . . ?
C2_2 C1_2 H1A_2 109.7 . . ?
N1_2 C1_2 H1AB_2 109.7 . . ?
C2_2 C1_2 H1AB_2 109.7 . . ?
H1A_2 C1_2 H1AB_2 108.2 . . ?
C3_3 C2_3 C1_3 119.74(16) . . ?
C3_3 C2_3 H2_3 120.1 . . ?
C1_3 C2_3 H2_3 120.1 . . ?
C6_3 C1_3 C2_3 120.31(17) . . ?
C6_3 C1_3 H1_3 119.8 . . ?
C2_3 C1_3 H1_3 119.8 . . ?
C2_3 C3_3 C4_3 120.21(19) . . ?
C2_3 C3_3 H3_3 119.9 . . ?
C4_3 C3_3 H3_3 119.9 . . ?
C3_3 C4_3 C5_3 119.93(17) . . ?
C3_3 C4_3 H4_3 120.0 . . ?
C5_3 C4_3 H4_3 120.0 . . ?
C6_3 C5_3 C4_3 119.92(16) . . ?
C6_3 C5_3 H5_3 120.0 . . ?
C4_3 C5_3 H5_3 120.0 . . ?
C1_3 C6_3 C5_3 119.87(18) . . ?
C1_3 C6_3 H6_3 120.1 . . ?
C5_3 C6_3 H6_3 120.1 . . ?

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
C8 C1 C2 C3 -1.23(19) . . . . ?
C9 C1 C2 C3 179.42(12) . . . . ?
C1 C2 C3 C6 1.75(19) . . . . ?
C1 C2 C3 C4 -177.82(13) . . . . ?
C2 C3 C4 N1_1 64.2(2) . . . . ?
C6 C3 C4 N1_1 -115.44(14) . . . . ?
C2 C3 C4 C5 -177.38(14) . . . . ?
C6 C3 C4 C5 3.01(12) . . . . ?
C5 N1 C6 C7 179.18(12) . . . . ?
C5 N1 C6 C3 0.30(15) . . . . ?
C2 C3 C6 C7 -0.93(19) . . . . ?
C4 C3 C6 C7 178.73(12) . . . . ?
C2 C3 C6 N1 178.00(12) . . . . ?
C4 C3 C6 N1 -2.34(15) . . . . ?
C6 N1 C5 N1_2 179.89(12) . . . . ?
C6 N1 C5 C4 1.93(14) . . . . ?
N1_1 C4 C5 N1 120.43(17) . . . . ?
C3 C4 C5 N1 -3.14(14) . . . . ?
N1_1 C4 C5 N1_2 -57.54(19) . . . . ?
C3 C4 C5 N1_2 178.89(12) . . . . ?
C2 C1 C8 C7 -0.14(19) . . . . ?
C9 C1 C8 C7 179.21(12) . . . . ?
C1 C8 C7 C6 0.98(19) . . . . ?
N1 C6 C7 C8 -179.26(12) . . . . ?
C3 C6 C7 C8 -0.46(19) . . . . ?
C3 C4 N1_1 C5_1 51.29(16) . . . . ?
C5 C4 N1_1 C5_1 -60.82(17) . . . . ?
C3 C4 N1_1 C1_1 -75.51(17) . . . . ?
C5 C4 N1_1 C1_1 172.39(11) . . . . ?
C1_1 C2_1 C3_1 C4_1 53.44(19) . . . . ?
C2_1 C3_1 C4_1 C5_1 -53.70(19) . . . . ?
C1_1 N1_1 C5_1 C4_1 -61.54(18) . . . . ?
C4 N1_1 C5_1 C4_1 170.96(11) . . . . ?
C3_1 C4_1 C5_1 N1_1 57.38(18) . . . . ?
C5_1 N1_1 C1_1 C2_1 61.3(2) . . . . ?
C4 N1_1 C1_1 C2_1 -170.79(11) . . . . ?
C3_1 C2_1 C1_1 N1_1 -56.90(18) . . . . ?
N1 C5 N1_2 C1_2 178.83(12) . . . . ?
C4 C5 N1_2 C1_2 -3.37(19) . . . . ?
N1 C5 N1_2 C5_2 -7.02(19) . . . . ?
C4 C5 N1_2 C5_2 170.78(12) . . . . ?
C1_2 C2_2 C3_2 C4_2 -53.43(19) . . . . ?
C2_2 C3_2 C4_2 C5_2 53.9(2) . . . . ?
C5 N1_2 C5_2 C4_2 -115.95(19) . . . . ?
C1_2 N1_2 C5_2 C4_2 58.77(19) . . . . ?
C3_2 C4_2 C5_2 N1_2 -55.18(19) . . . . ?
C5 N1_2 C1_2 C2_2 116.6(2) . . . . ?
C5_2 N1_2 C1_2 C2_2 -57.9(2) . . . . ?
C3_2 C2_2 C1_2 N1_2 53.84(19) . . . . ?
C3_3 C2_3 C1_3 C6_3 -0.3(2) . . . . ?
C1_3 C2_3 C3_3 C4_3 0.8(2) . . . . ?
C2_3 C3_3 C4_3 C5_3 -0.7(2) . . . . ?
C3_3 C4_3 C5_3 C6_3 0.3(2) . . . . ?
C2_3 C1_3 C6_3 C5_3 -0.1(2) . . . . ?
C4_3 C5_3 C6_3 C1_3 0.2(2) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 2103237'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H27 N3 O'
_chemical_formula_sum            'C19 H27 N3 O'
_chemical_formula_weight         313.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.133(2)
_cell_length_b                   11.723(4)
_cell_length_c                   12.936(6)
_cell_angle_alpha                114.651(15)
_cell_angle_beta                 96.357(16)
_cell_angle_gamma                95.980(14)
_cell_volume                     828.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7214
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      26.79


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.781
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.119
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5820
_exptl_absorpt_correction_T_max  0.7454
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.1210
0.00 0.00 -1.00 0.0030
-1.00 0.00 1.00 0.2060
1.00 0.00 -1.00 0.3310
1.00 1.00 0.00 0.3450
-1.00 -1.00 0.00 0.1660
1.00 1.00 -1.00 0.3420
0.00 1.00 0.00 0.1160
0.00 -1.00 0.00 0.0080
0.00 1.00 -1.00 0.0610
0.00 -1.00 1.00 0.0540

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon II)'
_diffrn_detector_area_resol_mean 7.5
_diffrn_reflns_number            11291
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3247
_reflns_number_gt                2911
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²+0.2858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O001 O 0.45465(17) 0.11829(9) 0.16891(8) 0.0198(2) Uani 1 1 d . . . . .
N002 N 0.29837(18) 0.12876(10) 0.58672(9) 0.0148(3) Uani 1 1 d . . . . .
N003 N 0.76982(17) 0.34975(10) 0.64685(9) 0.0130(3) Uani 1 1 d . . . . .
N004 N 0.54380(18) 0.20053(11) 0.75964(9) 0.0155(3) Uani 1 1 d . . . . .
C005 C 0.4966(2) 0.17818(11) 0.64798(11) 0.0130(3) Uani 1 1 d . . . . .
C006 C 0.1391(2) 0.07745(12) 0.38386(11) 0.0155(3) Uani 1 1 d . . . . .
H006 H -0.005606 0.046725 0.390748 0.019 Uiso 1 1 calc R U . . .
C007 C 0.3118(2) 0.12340(12) 0.47639(11) 0.0137(3) Uani 1 1 d . . . . .
C008 C 0.1820(2) 0.07718(12) 0.27960(11) 0.0165(3) Uani 1 1 d . . . . .
H008 H 0.064900 0.047549 0.215330 0.020 Uiso 1 1 calc R U . . .
C009 C 0.5255(2) 0.16975(11) 0.46719(11) 0.0137(3) Uani 1 1 d . . . . .
C00A C 0.6709(2) 0.21400(12) 0.58453(10) 0.0130(3) Uani 1 1 d . . . . .
H00A H 0.790642 0.160725 0.577347 0.016 Uiso 1 1 calc R U . . .
C00B C 0.3950(2) 0.12005(12) 0.26989(11) 0.0158(3) Uani 1 1 d . . . . .
C00C C 0.5706(2) 0.16691(12) 0.36381(11) 0.0148(3) Uani 1 1 d . . . . .
H00C H 0.716176 0.195828 0.356610 0.018 Uiso 1 1 calc R U . . .
C00D C 0.3683(2) 0.17069(12) 0.81677(11) 0.0160(3) Uani 1 1 d . . . . .
H00B H 0.399782 0.100157 0.836205 0.019 Uiso 1 1 calc R U . . .
H00D H 0.223613 0.142928 0.763991 0.019 Uiso 1 1 calc R U . . .
C00E C 0.7647(2) 0.24583(12) 0.83006(11) 0.0155(3) Uani 1 1 d . . . . .
H00E H 0.872060 0.266395 0.786072 0.019 Uiso 1 1 calc R U . . .
H00F H 0.813134 0.178213 0.849594 0.019 Uiso 1 1 calc R U . . .
C00F C 0.9543(2) 0.38256(12) 0.59571(11) 0.0159(3) Uani 1 1 d . . . . .
H00G H 0.896360 0.375864 0.518509 0.019 Uiso 1 1 calc R U . . .
H00H H 1.060336 0.322159 0.586216 0.019 Uiso 1 1 calc R U . . .
C00G C 0.6065(2) 0.43503(12) 0.65851(11) 0.0163(3) Uani 1 1 d . . . . .
H00I H 0.480177 0.408789 0.689690 0.020 Uiso 1 1 calc R U . . .
H00J H 0.548099 0.429345 0.581734 0.020 Uiso 1 1 calc R U . . .
C00H C 1.0736(2) 0.51774(13) 0.67325(12) 0.0185(3) Uani 1 1 d . . . . .
H00K H 1.193704 0.540367 0.636577 0.022 Uiso 1 1 calc R U . . .
H00L H 1.142488 0.522093 0.747998 0.022 Uiso 1 1 calc R U . . .
C00I C 0.5820(2) 0.33976(13) 1.00557(11) 0.0190(3) Uani 1 1 d . . . . .
H00M H 0.622117 0.278042 1.035289 0.023 Uiso 1 1 calc R U . . .
H00N H 0.573133 0.420236 1.072323 0.023 Uiso 1 1 calc R U . . .
C00J C 0.3562(2) 0.28753(13) 0.92638(11) 0.0172(3) Uani 1 1 d . . . . .
H00O H 0.245461 0.264695 0.967687 0.021 Uiso 1 1 calc R U . . .
H00P H 0.306297 0.354159 0.905763 0.021 Uiso 1 1 calc R U . . .
C00K C 0.7137(2) 0.57183(12) 0.73917(12) 0.0185(3) Uani 1 1 d . . . . .
H00Q H 0.762592 0.578625 0.817357 0.022 Uiso 1 1 calc R U . . .
H00R H 0.603108 0.629043 0.744720 0.022 Uiso 1 1 calc R U . . .
C00L C 0.7615(2) 0.36405(12) 0.94060(11) 0.0173(3) Uani 1 1 d . . . . .
H00S H 0.733199 0.435044 0.921222 0.021 Uiso 1 1 calc R U . . .
H00T H 0.908730 0.389412 0.990935 0.021 Uiso 1 1 calc R U . . .
C00M C 0.2820(2) 0.07116(15) 0.07159(12) 0.0227(3) Uani 1 1 d . . . . .
H00U H 0.342347 0.073875 0.005445 0.034 Uiso 1 1 calc R U . . .
H00V H 0.165040 0.123938 0.089070 0.034 Uiso 1 1 calc R U . . .
H00W H 0.219474 -0.016871 0.053051 0.034 Uiso 1 1 calc R U . . .
C00N C 0.9134(2) 0.61298(13) 0.69451(12) 0.0197(3) Uani 1 1 d . . . . .
H00X H 0.861767 0.618511 0.621725 0.024 Uiso 1 1 calc R U . . .
H00Y H 0.990968 0.698285 0.751766 0.024 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
O001 C00B 1.3878(17) . ?
O001 C00M 1.4191(17) . ?
N002 C005 1.3033(18) . ?
N002 C007 1.4143(17) . ?
N003 C00G 1.4637(17) . ?
N003 C00F 1.4675(16) . ?
N003 C00A 1.4734(17) . ?
N004 C005 1.3472(18) . ?
N004 C00E 1.4561(17) . ?
N004 C00D 1.4629(16) . ?
C005 C00A 1.5431(17) . ?
C006 C007 1.3814(19) . ?
C006 C008 1.4013(19) . ?
C006 H006 0.9500 . ?
C007 C009 1.4025(18) . ?
C008 C00B 1.388(2) . ?
C008 H008 0.9500 . ?
C009 C00C 1.3829(19) . ?
C009 C00A 1.5217(18) . ?
C00A H00A 1.0000 . ?
C00B C00C 1.403(2) . ?
C00C H00C 0.9500 . ?
C00D C00J 1.5221(19) . ?
C00D H00B 0.9900 . ?
C00D H00D 0.9900 . ?
C00E C00L 1.5246(19) . ?
C00E H00E 0.9900 . ?
C00E H00F 0.9900 . ?
C00F C00H 1.5239(19) . ?
C00F H00G 0.9900 . ?
C00F H00H 0.9900 . ?
C00G C00K 1.5250(19) . ?
C00G H00I 0.9900 . ?
C00G H00J 0.9900 . ?
C00H C00N 1.523(2) . ?
C00H H00K 0.9900 . ?
C00H H00L 0.9900 . ?
C00I C00J 1.5259(19) . ?
C00I C00L 1.5294(19) . ?
C00I H00M 0.9900 . ?
C00I H00N 0.9900 . ?
C00J H00O 0.9900 . ?
C00J H00P 0.9900 . ?
C00K C00N 1.5273(18) . ?
C00K H00Q 0.9900 . ?
C00K H00R 0.9900 . ?
C00L H00S 0.9900 . ?
C00L H00T 0.9900 . ?
C00M H00U 0.9800 . ?
C00M H00V 0.9800 . ?
C00M H00W 0.9800 . ?
C00N H00X 0.9900 . ?
C00N H00Y 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
C00B O001 C00M 116.32(11) . . ?
C005 N002 C007 106.17(11) . . ?
C00G N003 C00F 110.93(10) . . ?
C00G N003 C00A 113.23(10) . . ?
C00F N003 C00A 111.89(10) . . ?
C005 N004 C00E 125.13(11) . . ?
C005 N004 C00D 119.91(11) . . ?
C00E N004 C00D 114.83(10) . . ?
N002 C005 N004 122.45(12) . . ?
N002 C005 C00A 115.04(11) . . ?
N004 C005 C00A 122.47(11) . . ?
C007 C006 C008 118.50(12) . . ?
C007 C006 H006 120.8 . . ?
C008 C006 H006 120.8 . . ?
C006 C007 C009 121.11(12) . . ?
C006 C007 N002 125.84(12) . . ?
C009 C007 N002 113.04(11) . . ?
C00B C008 C006 120.24(12) . . ?
C00B C008 H008 119.9 . . ?
C006 C008 H008 119.9 . . ?
C00C C009 C007 120.74(12) . . ?
C00C C009 C00A 132.31(12) . . ?
C007 C009 C00A 106.94(11) . . ?
N003 C00A C009 117.81(10) . . ?
N003 C00A C005 110.99(10) . . ?
C009 C00A C005 98.78(10) . . ?
N003 C00A H00A 109.6 . . ?
C009 C00A H00A 109.6 . . ?
C005 C00A H00A 109.6 . . ?
O001 C00B C008 124.19(12) . . ?
O001 C00B C00C 114.47(12) . . ?
C008 C00B C00C 121.33(12) . . ?
C009 C00C C00B 118.03(12) . . ?
C009 C00C H00C 121.0 . . ?
C00B C00C H00C 121.0 . . ?
N004 C00D C00J 109.95(11) . . ?
N004 C00D H00B 109.7 . . ?
C00J C00D H00B 109.7 . . ?
N004 C00D H00D 109.7 . . ?
C00J C00D H00D 109.7 . . ?
H00B C00D H00D 108.2 . . ?
N004 C00E C00L 110.08(11) . . ?
N004 C00E H00E 109.6 . . ?
C00L C00E H00E 109.6 . . ?
N004 C00E H00F 109.6 . . ?
C00L C00E H00F 109.6 . . ?
H00E C00E H00F 108.2 . . ?
N003 C00F C00H 109.90(11) . . ?
N003 C00F H00G 109.7 . . ?
C00H C00F H00G 109.7 . . ?
N003 C00F H00H 109.7 . . ?
C00H C00F H00H 109.7 . . ?
H00G C00F H00H 108.2 . . ?
N003 C00G C00K 110.17(11) . . ?
N003 C00G H00I 109.6 . . ?
C00K C00G H00I 109.6 . . ?
N003 C00G H00J 109.6 . . ?
C00K C00G H00J 109.6 . . ?
H00I C00G H00J 108.1 . . ?
C00F C00H C00N 111.27(11) . . ?
C00F C00H H00K 109.4 . . ?
C00N C00H H00K 109.4 . . ?
C00F C00H H00L 109.4 . . ?
C00N C00H H00L 109.4 . . ?
H00K C00H H00L 108.0 . . ?
C00J C00I C00L 110.67(11) . . ?
C00J C00I H00M 109.5 . . ?
C00L C00I H00M 109.5 . . ?
C00J C00I H00N 109.5 . . ?
C00L C00I H00N 109.5 . . ?
H00M C00I H00N 108.1 . . ?
C00D C00J C00I 111.17(11) . . ?
C00D C00J H00O 109.4 . . ?
C00I C00J H00O 109.4 . . ?
C00D C00J H00P 109.4 . . ?
C00I C00J H00P 109.4 . . ?
H00O C00J H00P 108.0 . . ?
C00G C00K C00N 110.50(11) . . ?
C00G C00K H00Q 109.6 . . ?
C00N C00K H00Q 109.6 . . ?
C00G C00K H00R 109.6 . . ?
C00N C00K H00R 109.6 . . ?
H00Q C00K H00R 108.1 . . ?
C00E C00L C00I 111.30(11) . . ?
C00E C00L H00S 109.4 . . ?
C00I C00L H00S 109.4 . . ?
C00E C00L H00T 109.4 . . ?
C00I C00L H00T 109.4 . . ?
H00S C00L H00T 108.0 . . ?
O001 C00M H00U 109.5 . . ?
O001 C00M H00V 109.5 . . ?
H00U C00M H00V 109.5 . . ?
O001 C00M H00W 109.5 . . ?
H00U C00M H00W 109.5 . . ?
H00V C00M H00W 109.5 . . ?
C00H C00N C00K 110.20(11) . . ?
C00H C00N H00X 109.6 . . ?
C00K C00N H00X 109.6 . . ?
C00H C00N H00Y 109.6 . . ?
C00K C00N H00Y 109.6 . . ?
H00X C00N H00Y 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
C007 N002 C005 N004 178.29(11) . . . . ?
C007 N002 C005 C00A 0.56(15) . . . . ?
C00E N004 C005 N002 174.82(12) . . . . ?
C00D N004 C005 N002 -0.86(19) . . . . ?
C00E N004 C005 C00A -7.62(19) . . . . ?
C00D N004 C005 C00A 176.70(11) . . . . ?
C008 C006 C007 C009 0.45(19) . . . . ?
C008 C006 C007 N002 -179.00(11) . . . . ?
C005 N002 C007 C006 -179.95(12) . . . . ?
C005 N002 C007 C009 0.57(15) . . . . ?
C007 C006 C008 C00B 1.23(19) . . . . ?
C006 C007 C009 C00C -2.1(2) . . . . ?
N002 C007 C009 C00C 177.45(11) . . . . ?
C006 C007 C009 C00A 179.07(11) . . . . ?
N002 C007 C009 C00A -1.42(15) . . . . ?
C00G N003 C00A C009 52.31(14) . . . . ?
C00F N003 C00A C009 -73.96(14) . . . . ?
C00G N003 C00A C005 -60.48(13) . . . . ?
C00F N003 C00A C005 173.26(10) . . . . ?
C00C C009 C00A N003 63.41(19) . . . . ?
C007 C009 C00A N003 -117.91(12) . . . . ?
C00C C009 C00A C005 -177.17(13) . . . . ?
C007 C009 C00A C005 1.51(12) . . . . ?
N002 C005 C00A N003 123.07(12) . . . . ?
N004 C005 C00A N003 -54.65(16) . . . . ?
N002 C005 C00A C009 -1.32(13) . . . . ?
N004 C005 C00A C009 -179.05(12) . . . . ?
C00M O001 C00B C008 1.16(19) . . . . ?
C00M O001 C00B C00C 179.80(11) . . . . ?
C006 C008 C00B O001 177.20(12) . . . . ?
C006 C008 C00B C00C -1.3(2) . . . . ?
C007 C009 C00C C00B 1.93(19) . . . . ?
C00A C009 C00C C00B -179.54(12) . . . . ?
O001 C00B C00C C009 -178.93(11) . . . . ?
C008 C00B C00C C009 -0.2(2) . . . . ?
C005 N004 C00D C00J -126.07(12) . . . . ?
C00E N004 C00D C00J 57.83(15) . . . . ?
C005 N004 C00E C00L 126.67(13) . . . . ?
C00D N004 C00E C00L -57.47(14) . . . . ?
C00G N003 C00F C00H 61.17(14) . . . . ?
C00A N003 C00F C00H -171.32(10) . . . . ?
C00F N003 C00G C00K -61.92(13) . . . . ?
C00A N003 C00G C00K 171.30(10) . . . . ?
N003 C00F C00H C00N -56.71(15) . . . . ?
N004 C00D C00J C00I -54.59(14) . . . . ?
C00L C00I C00J C00D 53.66(15) . . . . ?
N003 C00G C00K C00N 57.60(14) . . . . ?
N004 C00E C00L C00I 53.96(14) . . . . ?
C00J C00I C00L C00E -53.31(15) . . . . ?
C00F C00H C00N C00K 53.05(15) . . . . ?
C00G C00K C00N C00H -53.18(15) . . . . ?

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2103238'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H33 N3'
_chemical_formula_sum            'C30 H33 N3'
_chemical_formula_weight         435.59

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.7901(17)
_cell_length_b                   9.3624(14)
_cell_length_c                   16.873(4)
_cell_angle_alpha                93.673(5)
_cell_angle_beta                 91.942(8)
_cell_angle_gamma                109.928(4)
_cell_volume                     1300.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.13
_cell_special_details            
;
To simulate systematic errors the final estimation of uncertainties in unit cell
parameters were based on 32 Monte-Carlo simulations.
;

_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.216
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_T_max  0.7455
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.1080
0.00 0.00 1.00 0.0260
0.00 2.00 -1.00 0.0920
0.00 -2.00 1.00 0.1320
-1.00 2.00 2.00 0.0540
1.00 -2.00 -2.00 0.1730
1.00 -1.00 -2.00 0.1550
-1.00 1.00 2.00 0.0380
1.00 0.00 -2.00 0.1570
-1.00 0.00 2.00 0.0320
2.00 1.00 -2.00 0.1640
2.00 -2.00 1.00 0.1230
1.00 2.00 1.00 0.1200
1.00 0.00 1.00 0.1170
2.00 1.00 0.00 0.1500
2.00 -1.00 -1.00 0.1650
-1.00 -1.00 -1.00 0.1020
-2.00 1.00 -2.00 0.0730
-2.00 -1.00 -2.00 0.0820
2.00 1.00 2.00 0.1190

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon II)'
_diffrn_detector_area_resol_mean 7.5
_diffrn_reflns_number            39208
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5302
_reflns_number_gt                4726
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.The atomic displacement parameters of 
atoms C1_1 > C5_20 were restraint with RIGU keyword in ShelXL input ('enhanced rigid 
bond' restraint for all bonds in the connectivity list. Standard values of 
0.005 for both parameters s1 and s2 were used).
The displacement parameters of atoms C1_1 > C5_20 of the residues RESI 1, RESI 2, 
RESI 10 and RESI 20 were restrained to the same value with similarity restraint SIMU.
The Uii displacement parameters of atoms C1_1 > C5_20 were restrained with ISOR 
keyword to approximate isotropic behavior.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.5453P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5302
_refine_ls_number_parameters     407
_refine_ls_number_restraints     642
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.019
_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 0.58981(11) 0.21048(11) 0.76715(6) 0.0194(2) Uani 1 1 d . . . . .
C1 C 0.62691(13) 0.36508(13) 0.65544(7) 0.0189(2) Uani 1 1 d . . . . .
N2 N 0.85574(11) 0.36281(11) 0.75442(6) 0.0200(2) Uani 1 1 d . . . . .
C2 C 0.69767(14) 0.31120(13) 0.72925(7) 0.0182(2) Uani 1 1 d . . . . .
C6 C 0.15182(14) 0.07368(14) 0.70106(8) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.048554 0.006713 0.713457 0.029 Uiso 1 1 calc R U . . .
C5 C 0.16266(14) 0.15414(14) 0.63427(7) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.067652 0.140847 0.601799 0.030 Uiso 1 1 calc R U . . .
C4 C 0.31204(14) 0.25490(13) 0.61403(7) 0.0213(2) Uani 1 1 d . . . . .
H4 H 0.319400 0.313522 0.569478 0.026 Uiso 1 1 calc R U . . .
C3 C 0.44844(14) 0.26656(13) 0.66077(7) 0.0197(2) Uani 1 1 d . . . . .
C9 C 0.43751(14) 0.18281(13) 0.72771(7) 0.0198(2) Uani 1 1 d . . . . .
C8 C 0.28759(14) 0.08717(13) 0.75126(7) 0.0211(2) Uani 1 1 d . . . . .
C10 C 0.12547(17) -0.02516(15) 0.86558(9) 0.0341(3) Uani 1 1 d . . . . .
H10 H 0.041536 0.007889 0.845907 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1044(2) -0.10308(17) 0.93366(10) 0.0444(4) Uani 1 1 d . . . . .
H11 H 0.006410 -0.123018 0.960098 0.053 Uiso 1 1 calc R U . . .
C12 C 0.2245(2) -0.15192(17) 0.96333(9) 0.0433(4) Uani 1 1 d . . . . .
H12 H 0.209251 -0.206261 1.009772 0.052 Uiso 1 1 calc R U . . .
C13 C 0.36787(19) -0.12116(16) 0.92490(9) 0.0370(3) Uani 1 1 d . . . . .
H13 H 0.451547 -0.153734 0.945365 0.044 Uiso 1 1 calc R U . . .
C14 C 0.38953(16) -0.04289(14) 0.85661(8) 0.0280(3) Uani 1 1 d . . . . .
H14 H 0.488366 -0.022201 0.830876 0.034 Uiso 1 1 calc R U . . .
C15 C 0.90914(14) 0.28155(14) 0.81510(7) 0.0231(3) Uani 1 1 d . . . . .
H15A H 0.949361 0.205091 0.788557 0.028 Uiso 1 1 calc R U . . .
H15B H 0.815437 0.226555 0.845506 0.028 Uiso 1 1 calc R U . . .
C16 C 1.04189(16) 0.38874(16) 0.87203(8) 0.0320(3) Uani 1 1 d . . . . .
H16A H 1.081725 0.328897 0.908578 0.038 Uiso 1 1 calc R U . . .
H16B H 0.997613 0.455768 0.904376 0.038 Uiso 1 1 calc R U . . .
C17 C 1.18227(16) 0.48601(17) 0.82655(9) 0.0353(3) Uani 1 1 d . . . . .
H17A H 1.232527 0.420102 0.797357 0.042 Uiso 1 1 calc R U . . .
H17B H 1.265871 0.558832 0.864215 0.042 Uiso 1 1 calc R U . . .
C18 C 1.11780(15) 0.57289(15) 0.76797(8) 0.0291(3) Uani 1 1 d . . . . .
H18A H 1.073233 0.642807 0.797728 0.035 Uiso 1 1 calc R U . . .
H18B H 1.207827 0.634967 0.737528 0.035 Uiso 1 1 calc R U . . .
C19 C 0.98624(14) 0.46330(14) 0.71076(7) 0.0227(2) Uani 1 1 d . . . . .
H19A H 0.941247 0.521874 0.675719 0.027 Uiso 1 1 calc R U . . .
H19B H 1.033637 0.401023 0.676843 0.027 Uiso 1 1 calc R U . . .
C7 C 0.26834(15) 0.00582(13) 0.82520(7) 0.0245(3) Uani 1 1 d . . . . .
C1_1 C 0.6588(5) 0.1705(5) 0.5635(2) 0.0198(8) Uani 0.3477(15) 1 d . U P A 1
H1_1 H 0.590756 0.095833 0.594473 0.024 Uiso 0.3477(15) 1 calc R U P A 1
C2_1 C 0.7226(5) 0.1236(4) 0.4967(2) 0.0243(7) Uani 0.3477(15) 1 d . U P A 1
H2_1 H 0.696640 0.017940 0.482258 0.029 Uiso 0.3477(15) 1 calc R U P A 1
C3_1 C 0.8235(6) 0.2295(5) 0.4512(3) 0.0254(8) Uani 0.3477(15) 1 d . U P A 1
H3_1 H 0.866775 0.196833 0.405440 0.030 Uiso 0.3477(15) 1 calc R U P A 1
C4_1 C 0.8614(5) 0.3844(4) 0.4726(2) 0.0277(7) Uani 0.3477(15) 1 d . U P A 1
H4_1 H 0.930503 0.457833 0.441346 0.033 Uiso 0.3477(15) 1 calc R U P A 1
C5_1 C 0.7978(4) 0.4315(4) 0.5400(2) 0.0228(7) Uani 0.3477(15) 1 d . U P A 1
H5_1 H 0.827913 0.537861 0.553914 0.027 Uiso 0.3477(15) 1 calc R U P A 1
C6_1 C 0.694(2) 0.3326(19) 0.5876(8) 0.0169(13) Uani 0.3477(15) 1 d . U P A 1
N1_2 N 0.6598(19) 0.5397(18) 0.6658(9) 0.0151(13) Uani 0.3477(15) 1 d . U P A 1
C1_2 C 0.6342(6) 0.5961(5) 0.7505(3) 0.0191(8) Uani 0.3477(15) 1 d . U P A 1
H1A_2 H 0.517276 0.559305 0.760193 0.023 Uiso 0.3477(15) 1 calc R U P A 1
H1AB_2 H 0.691095 0.555759 0.790176 0.023 Uiso 0.3477(15) 1 calc R U P A 1
C2_2 C 0.7007(5) 0.7693(4) 0.7586(2) 0.0234(7) Uani 0.3477(15) 1 d . U P A 1
H2A_2 H 0.819307 0.804923 0.753277 0.028 Uiso 0.3477(15) 1 calc R U P A 1
H2AB_2 H 0.680619 0.806330 0.812149 0.028 Uiso 0.3477(15) 1 calc R U P A 1
C3_2 C 0.6222(7) 0.8363(7) 0.6958(4) 0.0259(10) Uani 0.3477(15) 1 d . U P A 1
H3A_2 H 0.677580 0.948127 0.698192 0.031 Uiso 0.3477(15) 1 calc R U P A 1
H3AB_2 H 0.506969 0.815967 0.706450 0.031 Uiso 0.3477(15) 1 calc R U P A 1
C4_2 C 0.6337(5) 0.7657(4) 0.6129(2) 0.0260(7) Uani 0.3477(15) 1 d . U P A 1
H4A_2 H 0.572037 0.800786 0.573056 0.031 Uiso 0.3477(15) 1 calc R U P A 1
H4AB_2 H 0.748380 0.798369 0.598957 0.031 Uiso 0.3477(15) 1 calc R U P A 1
C5_2 C 0.5648(4) 0.5922(4) 0.6121(2) 0.0210(7) Uani 0.3477(15) 1 d . U P A 1
H5A_2 H 0.451318 0.560015 0.627793 0.025 Uiso 0.3477(15) 1 calc R U P A 1
H5AB_2 H 0.565198 0.546335 0.557571 0.025 Uiso 0.3477(15) 1 calc R U P A 1
C1_10 C 0.6484(12) 0.5314(12) 0.6708(6) 0.0169(9) Uani 0.6523(15) 1 d . U P A 2
C2_10 C 0.7407(2) 0.6437(2) 0.62163(10) 0.0198(4) Uani 0.6523(15) 1 d . U P A 2
H2_10 H 0.794186 0.615961 0.578391 0.024 Uiso 0.6523(15) 1 calc R U P A 2
C3_10 C 0.7517(2) 0.7952(2) 0.63781(11) 0.0245(4) Uani 0.6523(15) 1 d . U P A 2
H3_10 H 0.811417 0.870417 0.604689 0.029 Uiso 0.6523(15) 1 calc R U P A 2
C4_10 C 0.6766(3) 0.8369(4) 0.7015(2) 0.0251(6) Uani 0.6523(15) 1 d . U P A 2
H4_10 H 0.684490 0.940133 0.712349 0.030 Uiso 0.6523(15) 1 calc R U P A 2
C5_10 C 0.5891(3) 0.7253(2) 0.74962(12) 0.0275(4) Uani 0.6523(15) 1 d . U P A 2
H5_10 H 0.539057 0.752875 0.794241 0.033 Uiso 0.6523(15) 1 calc R U P A 2
C6_10 C 0.5749(3) 0.5743(3) 0.73267(14) 0.0220(5) Uani 0.6523(15) 1 d . U P A 2
H6_10 H 0.512275 0.499302 0.765114 0.026 Uiso 0.6523(15) 1 calc R U P A 2
N1_20 N 0.7046(8) 0.3299(9) 0.5785(3) 0.0154(8) Uani 0.6523(15) 1 d . U P A 2
C1_20 C 0.7306(3) 0.1851(2) 0.57197(13) 0.0192(4) Uani 0.6523(15) 1 d . U P A 2
H1A_20 H 0.625137 0.100890 0.563685 0.023 Uiso 0.6523(15) 1 calc R U P A 2
H1AB_20 H 0.785547 0.171914 0.621744 0.023 Uiso 0.6523(15) 1 calc R U P A 2
C2_20 C 0.8351(2) 0.1805(2) 0.50195(11) 0.0214(4) Uani 0.6523(15) 1 d . U P A 2
H2A_20 H 0.943909 0.258829 0.513135 0.026 Uiso 0.6523(15) 1 calc R U P A 2
H2AB_20 H 0.848464 0.079671 0.496173 0.026 Uiso 0.6523(15) 1 calc R U P A 2
C3_20 C 0.7608(3) 0.2090(2) 0.42418(13) 0.0235(4) Uani 0.6523(15) 1 d . U P A 2
H3A_20 H 0.662288 0.120694 0.407204 0.028 Uiso 0.6523(15) 1 calc R U P A 2
H3AB_20 H 0.839090 0.220278 0.382162 0.028 Uiso 0.6523(15) 1 calc R U P A 2
C4_20 C 0.7169(2) 0.3531(2) 0.43493(10) 0.0229(4) Uani 0.6523(15) 1 d . U P A 2
H4A_20 H 0.817016 0.443549 0.443363 0.028 Uiso 0.6523(15) 1 calc R U P A 2
H4AB_20 H 0.656392 0.363646 0.386400 0.028 Uiso 0.6523(15) 1 calc R U P A 2
C5_20 C 0.6135(2) 0.3441(2) 0.50613(10) 0.0196(4) Uani 0.6523(15) 1 d . U P A 2
H5A_20 H 0.584021 0.437066 0.512853 0.023 Uiso 0.6523(15) 1 calc R U P A 2
H5AB_20 H 0.512215 0.254943 0.497181 0.023 Uiso 0.6523(15) 1 calc R U P 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3061(15) . ?
N1 C9 1.4082(15) . ?
C1 C6_1 1.367(15) . ?
C1 C1_10 1.507(11) . ?
C1 C3 1.5342(16) . ?
C1 N1_20 1.555(5) . ?
C1 N1_2 1.557(16) . ?
C1 C2 1.5603(15) . ?
N2 C2 1.3492(15) . ?
N2 C19 1.4678(14) . ?
N2 C15 1.4690(14) . ?
C6 C5 1.3833(18) . ?
C6 C8 1.4045(17) . ?
C6 H6 0.9500 . ?
C5 C4 1.3993(17) . ?
C5 H5 0.9500 . ?
C4 C3 1.3809(16) . ?
C4 H4 0.9500 . ?
C3 C9 1.4034(16) . ?
C9 C8 1.4046(16) . ?
C8 C7 1.4878(17) . ?
C10 C11 1.384(2) . ?
C10 C7 1.4001(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3889(19) . ?
C13 H13 0.9500 . ?
C14 C7 1.3955(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.5146(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5260(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5294(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5200(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C1_1 C2_1 1.387(5) . ?
C1_1 C6_1 1.469(18) . ?
C1_1 H1_1 0.9500 . ?
C2_1 C3_1 1.380(6) . ?
C2_1 H2_1 0.9500 . ?
C3_1 C4_1 1.393(6) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.395(5) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.382(16) . ?
C5_1 H5_1 0.9500 . ?
N1_2 C5_2 1.431(18) . ?
N1_2 C1_2 1.540(16) . ?
C1_2 C2_2 1.520(6) . ?
C1_2 H1A_2 0.9900 . ?
C1_2 H1AB_2 0.9900 . ?
C2_2 C3_2 1.524(7) . ?
C2_2 H2A_2 0.9900 . ?
C2_2 H2AB_2 0.9900 . ?
C3_2 C4_2 1.529(7) . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3AB_2 0.9900 . ?
C4_2 C5_2 1.527(5) . ?
C4_2 H4A_2 0.9900 . ?
C4_2 H4AB_2 0.9900 . ?
C5_2 H5A_2 0.9900 . ?
C5_2 H5AB_2 0.9900 . ?
C1_10 C6_10 1.355(11) . ?
C1_10 C2_10 1.425(9) . ?
C2_10 C3_10 1.396(3) . ?
C2_10 H2_10 0.9500 . ?
C3_10 C4_10 1.384(4) . ?
C3_10 H3_10 0.9500 . ?
C4_10 C5_10 1.395(4) . ?
C4_10 H4_10 0.9500 . ?
C5_10 C6_10 1.386(3) . ?
C5_10 H5_10 0.9500 . ?
C6_10 H6_10 0.9500 . ?
N1_20 C1_20 1.447(8) . ?
N1_20 C5_20 1.476(7) . ?
C1_20 C2_20 1.528(3) . ?
C1_20 H1A_20 0.9900 . ?
C1_20 H1AB_20 0.9900 . ?
C2_20 C3_20 1.524(3) . ?
C2_20 H2A_20 0.9900 . ?
C2_20 H2AB_20 0.9900 . ?
C3_20 C4_20 1.526(3) . ?
C3_20 H3A_20 0.9900 . ?
C3_20 H3AB_20 0.9900 . ?
C4_20 C5_20 1.521(2) . ?
C4_20 H4A_20 0.9900 . ?
C4_20 H4AB_20 0.9900 . ?
C5_20 H5A_20 0.9900 . ?
C5_20 H5AB_20 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 C9 107.47(9) . . ?
C6_1 C1 C3 113.9(7) . . ?
C1_10 C1 C3 110.2(4) . . ?
C1_10 C1 N1_20 113.2(5) . . ?
C3 C1 N1_20 114.6(3) . . ?
C6_1 C1 N1_2 109.1(9) . . ?
C3 C1 N1_2 114.0(6) . . ?
C6_1 C1 C2 110.7(7) . . ?
C1_10 C1 C2 109.2(4) . . ?
C3 C1 C2 97.97(9) . . ?
N1_20 C1 C2 110.6(3) . . ?
N1_2 C1 C2 110.8(6) . . ?
C2 N2 C19 124.32(9) . . ?
C2 N2 C15 118.19(9) . . ?
C19 N2 C15 114.98(9) . . ?
N1 C2 N2 121.07(10) . . ?
N1 C2 C1 114.40(10) . . ?
N2 C2 C1 124.53(10) . . ?
C5 C6 C8 122.54(11) . . ?
C5 C6 H6 118.7 . . ?
C8 C6 H6 118.7 . . ?
C6 C5 C4 120.71(11) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C3 C4 C5 118.00(11) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C3 C9 121.14(11) . . ?
C4 C3 C1 131.05(11) . . ?
C9 C3 C1 107.78(10) . . ?
C3 C9 C8 121.58(11) . . ?
C3 C9 N1 112.36(10) . . ?
C8 C9 N1 126.03(11) . . ?
C6 C8 C9 115.89(11) . . ?
C6 C8 C7 120.52(11) . . ?
C9 C8 C7 123.58(11) . . ?
C11 C10 C7 121.16(14) . . ?
C11 C10 H10 119.4 . . ?
C7 C10 H10 119.4 . . ?
C12 C11 C10 120.43(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.50(14) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.23(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C7 121.02(13) . . ?
C13 C14 H14 119.5 . . ?
C7 C14 H14 119.5 . . ?
N2 C15 C16 112.04(10) . . ?
N2 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 110.67(11) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 C18 108.95(11) . . ?
C16 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
C16 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C19 C18 C17 110.80(11) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
N2 C19 C18 110.75(10) . . ?
N2 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C14 C7 C10 117.65(12) . . ?
C14 C7 C8 121.95(11) . . ?
C10 C7 C8 120.40(12) . . ?
C2_1 C1_1 C6_1 121.7(7) . . ?
C2_1 C1_1 H1_1 119.1 . . ?
C6_1 C1_1 H1_1 119.1 . . ?
C3_1 C2_1 C1_1 120.5(4) . . ?
C3_1 C2_1 H2_1 119.8 . . ?
C1_1 C2_1 H2_1 119.8 . . ?
C2_1 C3_1 C4_1 119.6(4) . . ?
C2_1 C3_1 H3_1 120.2 . . ?
C4_1 C3_1 H3_1 120.2 . . ?
C3_1 C4_1 C5_1 119.9(3) . . ?
C3_1 C4_1 H4_1 120.1 . . ?
C5_1 C4_1 H4_1 120.1 . . ?
C6_1 C5_1 C4_1 123.8(7) . . ?
C6_1 C5_1 H5_1 118.1 . . ?
C4_1 C5_1 H5_1 118.1 . . ?
C1 C6_1 C5_1 129.0(13) . . ?
C1 C6_1 C1_1 116.5(11) . . ?
C5_1 C6_1 C1_1 114.4(10) . . ?
C5_2 N1_2 C1_2 106.9(11) . . ?
C5_2 N1_2 C1 114.5(10) . . ?
C1_2 N1_2 C1 113.5(9) . . ?
C2_2 C1_2 N1_2 109.0(6) . . ?
C2_2 C1_2 H1A_2 109.9 . . ?
N1_2 C1_2 H1A_2 109.9 . . ?
C2_2 C1_2 H1AB_2 109.9 . . ?
N1_2 C1_2 H1AB_2 109.9 . . ?
H1A_2 C1_2 H1AB_2 108.3 . . ?
C1_2 C2_2 C3_2 111.6(4) . . ?
C1_2 C2_2 H2A_2 109.3 . . ?
C3_2 C2_2 H2A_2 109.3 . . ?
C1_2 C2_2 H2AB_2 109.3 . . ?
C3_2 C2_2 H2AB_2 109.3 . . ?
H2A_2 C2_2 H2AB_2 108.0 . . ?
C2_2 C3_2 C4_2 110.1(4) . . ?
C2_2 C3_2 H3A_2 109.6 . . ?
C4_2 C3_2 H3A_2 109.6 . . ?
C2_2 C3_2 H3AB_2 109.6 . . ?
C4_2 C3_2 H3AB_2 109.6 . . ?
H3A_2 C3_2 H3AB_2 108.1 . . ?
C5_2 C4_2 C3_2 109.5(3) . . ?
C5_2 C4_2 H4A_2 109.8 . . ?
C3_2 C4_2 H4A_2 109.8 . . ?
C5_2 C4_2 H4AB_2 109.8 . . ?
C3_2 C4_2 H4AB_2 109.8 . . ?
H4A_2 C4_2 H4AB_2 108.2 . . ?
N1_2 C5_2 C4_2 110.2(7) . . ?
N1_2 C5_2 H5A_2 109.6 . . ?
C4_2 C5_2 H5A_2 109.6 . . ?
N1_2 C5_2 H5AB_2 109.6 . . ?
C4_2 C5_2 H5AB_2 109.6 . . ?
H5A_2 C5_2 H5AB_2 108.1 . . ?
C6_10 C1_10 C2_10 119.2(8) . . ?
C6_10 C1_10 C1 118.7(6) . . ?
C2_10 C1_10 C1 122.1(8) . . ?
C3_10 C2_10 C1_10 119.1(5) . . ?
C3_10 C2_10 H2_10 120.4 . . ?
C1_10 C2_10 H2_10 120.4 . . ?
C4_10 C3_10 C2_10 120.8(2) . . ?
C4_10 C3_10 H3_10 119.6 . . ?
C2_10 C3_10 H3_10 119.6 . . ?
C3_10 C4_10 C5_10 119.0(3) . . ?
C3_10 C4_10 H4_10 120.5 . . ?
C5_10 C4_10 H4_10 120.5 . . ?
C6_10 C5_10 C4_10 120.4(2) . . ?
C6_10 C5_10 H5_10 119.8 . . ?
C4_10 C5_10 H5_10 119.8 . . ?
C1_10 C6_10 C5_10 121.5(4) . . ?
C1_10 C6_10 H6_10 119.3 . . ?
C5_10 C6_10 H6_10 119.3 . . ?
C1_20 N1_20 C5_20 109.4(4) . . ?
C1_20 N1_20 C1 116.0(4) . . ?
C5_20 N1_20 C1 111.8(5) . . ?
N1_20 C1_20 C2_20 109.4(3) . . ?
N1_20 C1_20 H1A_20 109.8 . . ?
C2_20 C1_20 H1A_20 109.8 . . ?
N1_20 C1_20 H1AB_20 109.8 . . ?
C2_20 C1_20 H1AB_20 109.8 . . ?
H1A_20 C1_20 H1AB_20 108.2 . . ?
C3_20 C2_20 C1_20 112.15(16) . . ?
C3_20 C2_20 H2A_20 109.2 . . ?
C1_20 C2_20 H2A_20 109.2 . . ?
C3_20 C2_20 H2AB_20 109.2 . . ?
C1_20 C2_20 H2AB_20 109.2 . . ?
H2A_20 C2_20 H2AB_20 107.9 . . ?
C2_20 C3_20 C4_20 110.24(17) . . ?
C2_20 C3_20 H3A_20 109.6 . . ?
C4_20 C3_20 H3A_20 109.6 . . ?
C2_20 C3_20 H3AB_20 109.6 . . ?
C4_20 C3_20 H3AB_20 109.6 . . ?
H3A_20 C3_20 H3AB_20 108.1 . . ?
C5_20 C4_20 C3_20 109.67(15) . . ?
C5_20 C4_20 H4A_20 109.7 . . ?
C3_20 C4_20 H4A_20 109.7 . . ?
C5_20 C4_20 H4AB_20 109.7 . . ?
C3_20 C4_20 H4AB_20 109.7 . . ?
H4A_20 C4_20 H4AB_20 108.2 . . ?
N1_20 C5_20 C4_20 109.6(3) . . ?
N1_20 C5_20 H5A_20 109.7 . . ?
C4_20 C5_20 H5A_20 109.7 . . ?
N1_20 C5_20 H5AB_20 109.7 . . ?
C4_20 C5_20 H5AB_20 109.7 . . ?
H5A_20 C5_20 H5AB_20 108.2 . . ?

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
C9 N1 C2 N2 178.72(10) . . . . ?
C9 N1 C2 C1 -0.49(13) . . . . ?
C19 N2 C2 N1 173.34(11) . . . . ?
C15 N2 C2 N1 12.26(16) . . . . ?
C19 N2 C2 C1 -7.53(18) . . . . ?
C15 N2 C2 C1 -168.61(10) . . . . ?
C6_1 C1 C2 N1 -119.8(8) . . . . ?
C1_10 C1 C2 N1 114.2(4) . . . . ?
C3 C1 C2 N1 -0.45(12) . . . . ?
N1_20 C1 C2 N1 -120.5(3) . . . . ?
N1_2 C1 C2 N1 119.0(6) . . . . ?
C6_1 C1 C2 N2 61.0(8) . . . . ?
C1_10 C1 C2 N2 -65.0(4) . . . . ?
C3 C1 C2 N2 -179.64(11) . . . . ?
N1_20 C1 C2 N2 60.3(3) . . . . ?
N1_2 C1 C2 N2 -60.1(6) . . . . ?
C8 C6 C5 C4 -0.47(18) . . . . ?
C6 C5 C4 C3 2.62(17) . . . . ?
C5 C4 C3 C9 -1.51(17) . . . . ?
C5 C4 C3 C1 -179.50(11) . . . . ?
C6_1 C1 C3 C4 -63.7(8) . . . . ?
C1_10 C1 C3 C4 65.6(4) . . . . ?
N1_20 C1 C3 C4 -63.5(3) . . . . ?
N1_2 C1 C3 C4 62.3(6) . . . . ?
C2 C1 C3 C4 179.41(12) . . . . ?
C6_1 C1 C3 C9 118.1(8) . . . . ?
C1_10 C1 C3 C9 -112.6(4) . . . . ?
N1_20 C1 C3 C9 118.3(3) . . . . ?
N1_2 C1 C3 C9 -115.9(6) . . . . ?
C2 C1 C3 C9 1.22(11) . . . . ?
C4 C3 C9 C8 -1.79(17) . . . . ?
C1 C3 C9 C8 176.62(10) . . . . ?
C4 C3 C9 N1 179.91(10) . . . . ?
C1 C3 C9 N1 -1.68(13) . . . . ?
C2 N1 C9 C3 1.38(13) . . . . ?
C2 N1 C9 C8 -176.83(11) . . . . ?
C5 C6 C8 C9 -2.70(17) . . . . ?
C5 C6 C8 C7 176.08(11) . . . . ?
C3 C9 C8 C6 3.80(16) . . . . ?
N1 C9 C8 C6 -178.14(11) . . . . ?
C3 C9 C8 C7 -174.94(11) . . . . ?
N1 C9 C8 C7 3.11(18) . . . . ?
C7 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C7 -0.2(2) . . . . ?
C2 N2 C15 C16 -144.88(11) . . . . ?
C19 N2 C15 C16 52.31(14) . . . . ?
N2 C15 C16 C17 -53.75(15) . . . . ?
C15 C16 C17 C18 56.92(16) . . . . ?
C16 C17 C18 C19 -58.18(15) . . . . ?
C2 N2 C19 C18 145.58(11) . . . . ?
C15 N2 C19 C18 -52.80(14) . . . . ?
C17 C18 C19 N2 55.49(14) . . . . ?
C13 C14 C7 C10 0.87(19) . . . . ?
C13 C14 C7 C8 -178.79(12) . . . . ?
C11 C10 C7 C14 -0.8(2) . . . . ?
C11 C10 C7 C8 178.84(13) . . . . ?
C6 C8 C7 C14 150.26(12) . . . . ?
C9 C8 C7 C14 -31.05(18) . . . . ?
C6 C8 C7 C10 -29.39(17) . . . . ?
C9 C8 C7 C10 149.30(12) . . . . ?
C6_1 C1_1 C2_1 C3_1 0.8(9) . . . . ?
C1_1 C2_1 C3_1 C4_1 0.1(7) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.2(7) . . . . ?
C3_1 C4_1 C5_1 C6_1 -1.5(10) . . . . ?
C3 C1 C6_1 C5_1 139.1(12) . . . . ?
N1_2 C1 C6_1 C5_1 10.5(18) . . . . ?
C2 C1 C6_1 C5_1 -111.7(13) . . . . ?
C3 C1 C6_1 C1_1 -44.8(13) . . . . ?
N1_2 C1 C6_1 C1_1 -173.4(10) . . . . ?
C2 C1 C6_1 C1_1 64.4(12) . . . . ?
C4_1 C5_1 C6_1 C1 178.5(10) . . . . ?
C4_1 C5_1 C6_1 C1_1 2.3(15) . . . . ?
C2_1 C1_1 C6_1 C1 -178.6(7) . . . . ?
C2_1 C1_1 C6_1 C5_1 -1.9(15) . . . . ?
C6_1 C1 N1_2 C5_2 73.3(12) . . . . ?
C3 C1 N1_2 C5_2 -55.2(11) . . . . ?
C2 C1 N1_2 C5_2 -164.6(7) . . . . ?
C6_1 C1 N1_2 C1_2 -163.6(10) . . . . ?
C3 C1 N1_2 C1_2 67.9(11) . . . . ?
C2 C1 N1_2 C1_2 -41.5(11) . . . . ?
C5_2 N1_2 C1_2 C2_2 -63.9(9) . . . . ?
C1 N1_2 C1_2 C2_2 169.0(8) . . . . ?
N1_2 C1_2 C2_2 C3_2 56.7(8) . . . . ?
C1_2 C2_2 C3_2 C4_2 -52.1(5) . . . . ?
C2_2 C3_2 C4_2 C5_2 53.1(5) . . . . ?
C1_2 N1_2 C5_2 C4_2 67.3(9) . . . . ?
C1 N1_2 C5_2 C4_2 -166.2(7) . . . . ?
C3_2 C4_2 C5_2 N1_2 -63.2(8) . . . . ?
C3 C1 C1_10 C6_10 45.1(8) . . . . ?
N1_20 C1 C1_10 C6_10 174.9(6) . . . . ?
C2 C1 C1_10 C6_10 -61.4(8) . . . . ?
C3 C1 C1_10 C2_10 -133.8(7) . . . . ?
N1_20 C1 C1_10 C2_10 -4.0(9) . . . . ?
C2 C1 C1_10 C2_10 119.7(7) . . . . ?
C6_10 C1_10 C2_10 C3_10 -0.8(10) . . . . ?
C1 C1_10 C2_10 C3_10 178.1(5) . . . . ?
C1_10 C2_10 C3_10 C4_10 1.2(5) . . . . ?
C2_10 C3_10 C4_10 C5_10 -0.1(3) . . . . ?
C3_10 C4_10 C5_10 C6_10 -1.4(4) . . . . ?
C2_10 C1_10 C6_10 C5_10 -0.7(10) . . . . ?
C1 C1_10 C6_10 C5_10 -179.6(5) . . . . ?
C4_10 C5_10 C6_10 C1_10 1.8(6) . . . . ?
C1_10 C1 N1_20 C1_20 162.7(5) . . . . ?
C3 C1 N1_20 C1_20 -69.8(5) . . . . ?
C2 C1 N1_20 C1_20 39.8(5) . . . . ?
C1_10 C1 N1_20 C5_20 -71.1(6) . . . . ?
C3 C1 N1_20 C5_20 56.4(5) . . . . ?
C2 C1 N1_20 C5_20 166.0(3) . . . . ?
C5_20 N1_20 C1_20 C2_20 63.0(5) . . . . ?
C1 N1_20 C1_20 C2_20 -169.5(3) . . . . ?
N1_20 C1_20 C2_20 C3_20 -56.3(4) . . . . ?
C1_20 C2_20 C3_20 C4_20 50.9(2) . . . . ?
C2_20 C3_20 C4_20 C5_20 -52.3(2) . . . . ?
C1_20 N1_20 C5_20 C4_20 -66.0(4) . . . . ?
C1 N1_20 C5_20 C4_20 164.2(3) . . . . ?
C3_20 C4_20 C5_20 N1_20 59.9(4) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 2103240'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H30 N6'
_chemical_formula_sum            'C20 H30 N6'
_chemical_formula_weight         354.50

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.1184(16)
_cell_length_b                   10.4276(18)
_cell_length_c                   10.849(2)
_cell_angle_alpha                88.78(2)
_cell_angle_beta                 72.367(9)
_cell_angle_gamma                76.798(9)
_cell_volume                     955.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.29


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_T_max  0.7457
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 -3.00 1.00 0.0980
0.00 -3.00 1.00 0.0790
0.00 3.00 -1.00 0.0810
3.00 -2.00 1.00 0.0290
-3.00 2.00 -1.00 0.1360
-1.00 3.00 -2.00 0.0960
-1.00 1.00 -1.00 0.1220
-3.00 0.00 -1.00 0.1540
2.00 -1.00 3.00 0.0220
-2.00 1.00 -3.00 0.1110
-2.00 -1.00 0.00 0.1420
-1.00 -1.00 3.00 0.0960
1.00 1.00 -3.00 0.0450
-2.00 -1.00 -1.00 0.1540
0.00 0.00 -1.00 0.0750
0.00 0.00 1.00 0.0850
-3.00 -2.00 -3.00 0.1390
-2.00 -1.00 3.00 0.1170
0.00 1.00 3.00 0.1060
0.00 -1.00 -3.00 0.0770

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon II)'
_diffrn_detector_area_resol_mean 7.5
_diffrn_reflns_number            21531
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.410
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3892
_reflns_number_gt                3452
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.4502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3892
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.69562(13) 0.64443(10) 0.95826(10) 0.0188(2) Uani 1 1 d . . . . .
C1 C 0.52098(16) 0.67968(13) 0.99786(13) 0.0216(3) Uani 1 1 d . . . . .
H1A H 0.479080 0.611162 1.052772 0.026 Uiso 1 1 calc R U . . .
H1AB H 0.485009 0.683646 0.920141 0.026 Uiso 1 1 calc R U . . .
N2 N 0.68792(13) 0.62844(10) 0.66532(11) 0.0166(2) Uani 1 1 d . . . . .
C2 C 0.45768(18) 0.81258(14) 1.07276(14) 0.0267(3) Uani 1 1 d . . . . .
H2A H 0.340547 0.833727 1.101602 0.032 Uiso 1 1 calc R U . . .
H2AB H 0.492898 0.882168 1.015686 0.032 Uiso 1 1 calc R U . . .
N4 N 0.85557(14) 0.42298(11) 0.88392(11) 0.0211(2) Uani 1 1 d . . . . .
C4 C 0.69681(18) 0.76175(14) 1.14994(14) 0.0271(3) Uani 1 1 d . . . . .
H4A H 0.745854 0.828233 1.096953 0.033 Uiso 1 1 calc R U . . .
H4AB H 0.732026 0.751833 1.228149 0.033 Uiso 1 1 calc R U . . .
N3 N 0.87586(14) 0.15420(11) 0.22741(11) 0.0228(3) Uani 1 1 d . . . . .
C3 C 0.51708(18) 0.80980(15) 1.19037(14) 0.0291(3) Uani 1 1 d . . . . .
H3A H 0.485597 0.899426 1.232404 0.035 Uiso 1 1 calc R U . . .
H3AB H 0.468068 0.750444 1.253952 0.035 Uiso 1 1 calc R U . . .
N6 N 0.83845(13) 0.41142(10) 0.69061(11) 0.0176(2) Uani 1 1 d . . . . .
C6 C 0.54346(15) 0.61386(12) 0.63925(13) 0.0180(3) Uani 1 1 d . . . . .
H6A H 0.449827 0.651660 0.713809 0.022 Uiso 1 1 calc R U . . .
H6AB H 0.547429 0.519185 0.626955 0.022 Uiso 1 1 calc R U . . .
N5 N 0.90009(14) 0.34411(11) 0.77898(11) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.75188(17) 0.63004(13) 1.07220(13) 0.0223(3) Uani 1 1 d . . . . .
H5A H 0.868861 0.602442 1.044424 0.027 Uiso 1 1 calc R U . . .
H5AB H 0.709343 0.561490 1.126626 0.027 Uiso 1 1 calc R U . . .
C8 C 0.53611(16) 0.82897(13) 0.53049(13) 0.0207(3) Uani 1 1 d . . . . .
H8A H 0.536662 0.871362 0.447892 0.025 Uiso 1 1 calc R U . . .
H8AB H 0.440734 0.876367 0.598946 0.025 Uiso 1 1 calc R U . . .
C7 C 0.52965(16) 0.68505(12) 0.51770(13) 0.0196(3) Uani 1 1 d . . . . .
H7A H 0.428526 0.680849 0.503561 0.024 Uiso 1 1 calc R U . . .
H7AB H 0.617179 0.640597 0.441713 0.024 Uiso 1 1 calc R U . . .
C9 C 0.68382(16) 0.83904(12) 0.56437(13) 0.0207(3) Uani 1 1 d . . . . .
H9A H 0.779157 0.800790 0.491354 0.025 Uiso 1 1 calc R U . . .
H9AB H 0.681895 0.932976 0.578466 0.025 Uiso 1 1 calc R U . . .
C10 C 0.69199(16) 0.76607(12) 0.68599(13) 0.0191(3) Uani 1 1 d . . . . .
H10A H 0.790835 0.769474 0.704655 0.023 Uiso 1 1 calc R U . . .
H10B H 0.601241 0.808270 0.760887 0.023 Uiso 1 1 calc R U . . .
C11 C 0.76444(15) 0.53957(12) 0.86409(13) 0.0176(3) Uani 1 1 d . . . . .
C12 C 0.75336(15) 0.53564(12) 0.73985(12) 0.0165(3) Uani 1 1 d . . . . .
C13 C 0.85828(15) 0.34609(12) 0.56986(12) 0.0172(3) Uani 1 1 d . . . . .
C14 C 0.86305(15) 0.21182(12) 0.56581(13) 0.0187(3) Uani 1 1 d . . . . .
H14 H 0.856334 0.164389 0.642288 0.022 Uiso 1 1 calc R U . . .
C15 C 0.87748(15) 0.14683(12) 0.45130(13) 0.0187(3) Uani 1 1 d . . . . .
H15 H 0.885102 0.054449 0.449491 0.022 Uiso 1 1 calc R U . . .
C16 C 0.88106(15) 0.21509(12) 0.33748(13) 0.0183(3) Uani 1 1 d . . . . .
C17 C 0.88374(15) 0.35006(12) 0.34233(13) 0.0187(3) Uani 1 1 d . . . . .
H17 H 0.892760 0.397887 0.265930 0.022 Uiso 1 1 calc R U . . .
C18 C 0.87345(15) 0.41362(12) 0.45653(13) 0.0178(3) Uani 1 1 d . . . . .
H18 H 0.876774 0.503983 0.457377 0.021 Uiso 1 1 calc R U . . .
C19 C 0.9160(2) 0.01150(14) 0.21310(15) 0.0323(4) Uani 1 1 d . . . . .
H19A H 0.898038 -0.016071 0.134136 0.048 Uiso 1 1 calc R U . . .
H19B H 0.849505 -0.024089 0.288243 0.048 Uiso 1 1 calc R U . . .
H19C H 1.027572 -0.021858 0.207250 0.048 Uiso 1 1 calc R U . . .
C20 C 0.8988(2) 0.22396(14) 0.10856(14) 0.0287(3) Uani 1 1 d . . . . .
H20A H 1.007308 0.236037 0.078542 0.043 Uiso 1 1 calc R U . . .
H20B H 0.824063 0.310328 0.124570 0.043 Uiso 1 1 calc R U . . .
H20C H 0.880627 0.172683 0.042243 0.043 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 C11 1.4067(17) . ?
N1 C5 1.4680(17) . ?
N1 C1 1.4766(17) . ?
C1 C2 1.5206(19) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
N2 C12 1.3935(16) . ?
N2 C10 1.4677(15) . ?
N2 C6 1.4688(16) . ?
C2 C3 1.527(2) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
N4 N5 1.3209(16) . ?
N4 C11 1.3604(17) . ?
C4 C5 1.5255(19) . ?
C4 C3 1.526(2) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
N3 C16 1.3827(17) . ?
N3 C19 1.4487(18) . ?
N3 C20 1.4498(18) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
N6 N5 1.3585(15) . ?
N6 C12 1.3727(16) . ?
N6 C13 1.4322(17) . ?
C6 C7 1.5240(18) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C8 C9 1.5252(19) . ?
C8 C7 1.5261(18) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C9 C10 1.5222(18) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.3840(18) . ?
C13 C18 1.3898(18) . ?
C13 C14 1.3921(18) . ?
C14 C15 1.3842(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.4077(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.4156(18) . ?
C17 C18 1.3853(18) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C11 N1 C5 115.09(10) . . ?
C11 N1 C1 113.65(10) . . ?
C5 N1 C1 110.66(11) . . ?
N1 C1 C2 110.25(11) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1AB 109.6 . . ?
C2 C1 H1AB 109.6 . . ?
H1A C1 H1AB 108.1 . . ?
C12 N2 C10 116.99(10) . . ?
C12 N2 C6 118.22(10) . . ?
C10 N2 C6 113.67(10) . . ?
C1 C2 C3 110.32(12) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2AB 109.6 . . ?
C3 C2 H2AB 109.6 . . ?
H2A C2 H2AB 108.1 . . ?
N5 N4 C11 109.13(11) . . ?
C5 C4 C3 111.31(12) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4AB 109.4 . . ?
C3 C4 H4AB 109.4 . . ?
H4A C4 H4AB 108.0 . . ?
C16 N3 C19 119.47(11) . . ?
C16 N3 C20 118.99(11) . . ?
C19 N3 C20 116.30(11) . . ?
C4 C3 C2 110.55(12) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3AB 109.5 . . ?
C2 C3 H3AB 109.5 . . ?
H3A C3 H3AB 108.1 . . ?
N5 N6 C12 110.67(10) . . ?
N5 N6 C13 119.48(10) . . ?
C12 N6 C13 129.67(11) . . ?
N2 C6 C7 109.41(11) . . ?
N2 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
N2 C6 H6AB 109.8 . . ?
C7 C6 H6AB 109.8 . . ?
H6A C6 H6AB 108.2 . . ?
N4 N5 N6 107.27(10) . . ?
N1 C5 C4 109.11(11) . . ?
N1 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
N1 C5 H5AB 109.9 . . ?
C4 C5 H5AB 109.9 . . ?
H5A C5 H5AB 108.3 . . ?
C9 C8 C7 110.79(10) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8AB 109.5 . . ?
C7 C8 H8AB 109.5 . . ?
H8A C8 H8AB 108.1 . . ?
C6 C7 C8 110.69(11) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7AB 109.5 . . ?
C8 C7 H7AB 109.5 . . ?
H7A C7 H7AB 108.1 . . ?
C10 C9 C8 110.60(11) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9AB 109.5 . . ?
C8 C9 H9AB 109.5 . . ?
H9A C9 H9AB 108.1 . . ?
N2 C10 C9 108.77(10) . . ?
N2 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
N2 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
N4 C11 C12 109.07(11) . . ?
N4 C11 N1 123.43(11) . . ?
C12 C11 N1 127.50(11) . . ?
N6 C12 C11 103.84(11) . . ?
N6 C12 N2 122.18(11) . . ?
C11 C12 N2 133.82(12) . . ?
C18 C13 C14 119.24(12) . . ?
C18 C13 N6 121.49(11) . . ?
C14 C13 N6 119.26(12) . . ?
C15 C14 C13 120.56(12) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.22(12) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
N3 C16 C15 121.38(12) . . ?
N3 C16 C17 121.49(12) . . ?
C15 C16 C17 117.09(12) . . ?
C18 C17 C16 121.16(12) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 120.45(12) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C11 N1 C1 C2 -166.02(11) . . . . ?
C5 N1 C1 C2 62.69(14) . . . . ?
N1 C1 C2 C3 -57.18(15) . . . . ?
C5 C4 C3 C2 -53.26(17) . . . . ?
C1 C2 C3 C4 52.64(17) . . . . ?
C12 N2 C6 C7 -157.18(11) . . . . ?
C10 N2 C6 C7 59.92(14) . . . . ?
C11 N4 N5 N6 0.72(14) . . . . ?
C12 N6 N5 N4 0.16(14) . . . . ?
C13 N6 N5 N4 -175.48(11) . . . . ?
C11 N1 C5 C4 167.38(11) . . . . ?
C1 N1 C5 C4 -62.09(14) . . . . ?
C3 C4 C5 N1 57.51(16) . . . . ?
N2 C6 C7 C8 -55.10(14) . . . . ?
C9 C8 C7 C6 54.11(15) . . . . ?
C7 C8 C9 C10 -55.12(14) . . . . ?
C12 N2 C10 C9 155.98(11) . . . . ?
C6 N2 C10 C9 -60.63(14) . . . . ?
C8 C9 C10 N2 56.81(14) . . . . ?
N5 N4 C11 C12 -1.33(15) . . . . ?
N5 N4 C11 N1 178.83(12) . . . . ?
C5 N1 C11 N4 10.83(18) . . . . ?
C1 N1 C11 N4 -118.25(14) . . . . ?
C5 N1 C11 C12 -168.97(13) . . . . ?
C1 N1 C11 C12 61.95(17) . . . . ?
N5 N6 C12 C11 -0.93(14) . . . . ?
C13 N6 C12 C11 174.13(12) . . . . ?
N5 N6 C12 N2 174.99(11) . . . . ?
C13 N6 C12 N2 -9.9(2) . . . . ?
N4 C11 C12 N6 1.35(14) . . . . ?
N1 C11 C12 N6 -178.82(12) . . . . ?
N4 C11 C12 N2 -173.86(13) . . . . ?
N1 C11 C12 N2 6.0(2) . . . . ?
C10 N2 C12 N6 -141.88(12) . . . . ?
C6 N2 C12 N6 76.44(16) . . . . ?
C10 N2 C12 C11 32.6(2) . . . . ?
C6 N2 C12 C11 -109.06(16) . . . . ?
N5 N6 C13 C18 -147.22(12) . . . . ?
C12 N6 C13 C18 38.1(2) . . . . ?
N5 N6 C13 C14 32.55(17) . . . . ?
C12 N6 C13 C14 -142.15(13) . . . . ?
C18 C13 C14 C15 -2.11(19) . . . . ?
N6 C13 C14 C15 178.12(11) . . . . ?
C13 C14 C15 C16 -2.7(2) . . . . ?
C19 N3 C16 C15 -19.2(2) . . . . ?
C20 N3 C16 C15 -172.73(13) . . . . ?
C19 N3 C16 C17 163.36(13) . . . . ?
C20 N3 C16 C17 9.87(19) . . . . ?
C14 C15 C16 N3 -171.95(12) . . . . ?
C14 C15 C16 C17 5.56(19) . . . . ?
N3 C16 C17 C18 173.66(12) . . . . ?
C15 C16 C17 C18 -3.85(18) . . . . ?
C16 C17 C18 C13 -0.77(19) . . . . ?
C14 C13 C18 C17 3.81(19) . . . . ?
N6 C13 C18 C17 -176.42(11) . . . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2103242'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki '
;Institut fuer Anorganische Chemie Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-08-14 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 F4 N3'
_chemical_formula_sum            'C19 H23 F4 N3'
_chemical_formula_weight         369.40

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   25.7461(8)
_cell_length_b                   9.7101(3)
_cell_length_c                   16.6172(5)
_cell_angle_alpha                90
_cell_angle_beta                 121.8730(10)
_cell_angle_gamma                90
_cell_volume                     3527.88(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9803
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      35.52


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_T_max  0.7471
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 0.00 3.00 0.0380
2.00 0.00 -3.00 0.0780
1.00 0.00 -3.00 0.0900
-3.00 0.00 1.00 0.0360
3.00 0.00 -1.00 0.1330
3.00 -1.00 2.00 0.0940
-3.00 1.00 -2.00 0.0780
3.00 -1.00 -1.00 0.1310
-1.00 -1.00 1.00 0.0740
2.00 -3.00 0.00 0.1020
-2.00 3.00 0.00 0.0320
2.00 3.00 -2.00 0.0550
-2.00 -3.00 2.00 0.0800
-3.00 2.00 2.00 0.0170
3.00 -2.00 -2.00 0.1300
2.00 3.00 0.00 0.0400
-2.00 -3.00 0.00 0.0990
-1.00 -1.00 0.00 0.0960
1.00 1.00 0.00 0.0480
-1.00 -2.00 -3.00 0.1220

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon II)'
_diffrn_detector_area_resol_mean 7.5
_diffrn_reflns_number            58203
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        26.000
_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             3604
_reflns_number_gt                3280
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+2.0238P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3604
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
C1_1 C 0.34880(5) 0.60355(11) 0.20642(8) 0.0182(2) Uani 1 1 d . . . . .
H1A_1 H 0.320912 0.554168 0.220627 0.022 Uiso 1 1 calc R U . . .
H1AB_1 H 0.370299 0.534428 0.190583 0.022 Uiso 1 1 calc R U . . .
N1_1 N 0.39354(4) 0.68355(9) 0.28968(6) 0.0146(2) Uani 1 1 d . . . . .
C2_1 C 0.31199(5) 0.70033(13) 0.12238(8) 0.0208(2) Uani 1 1 d . . . . .
H2A_1 H 0.282803 0.645993 0.065845 0.025 Uiso 1 1 calc R U . . .
H2AB_1 H 0.288183 0.764885 0.136743 0.025 Uiso 1 1 calc R U . . .
C3_1 C 0.35410(5) 0.78179(13) 0.10120(8) 0.0222(2) Uani 1 1 d . . . . .
H3A_1 H 0.329884 0.850522 0.051043 0.027 Uiso 1 1 calc R U . . .
H3AB_1 H 0.373447 0.718595 0.077813 0.027 Uiso 1 1 calc R U . . .
C4_1 C 0.40360(5) 0.85505(12) 0.19049(8) 0.0201(2) Uani 1 1 d . . . . .
H4A_1 H 0.433165 0.899327 0.177706 0.024 Uiso 1 1 calc R U . . .
H4AB_1 H 0.384715 0.927855 0.208534 0.024 Uiso 1 1 calc R U . . .
C5_1 C 0.43697(5) 0.75261(11) 0.27166(8) 0.0166(2) Uani 1 1 d . . . . .
H5A_1 H 0.458161 0.683324 0.255347 0.020 Uiso 1 1 calc R U . . .
H5AB_1 H 0.468132 0.801545 0.329568 0.020 Uiso 1 1 calc R U . . .
C1_2 C 0.30115(5) 0.55635(12) 0.44207(8) 0.0198(2) Uani 1 1 d . . . . .
H1A_2 H 0.314138 0.586933 0.506895 0.024 Uiso 1 1 calc R U . . .
H1AB_2 H 0.304942 0.454829 0.442808 0.024 Uiso 1 1 calc R U . . .
N1_2 N 0.34085(4) 0.61872(10) 0.41363(7) 0.0179(2) Uani 1 1 d . . . . .
C2_2 C 0.23472(5) 0.59750(12) 0.37360(9) 0.0223(3) Uani 1 1 d . . . . .
H2A_2 H 0.209427 0.564112 0.398296 0.027 Uiso 1 1 calc R U . . .
H2AB_2 H 0.219725 0.552732 0.311572 0.027 Uiso 1 1 calc R U . . .
C3_2 C 0.22723(5) 0.75368(13) 0.35969(9) 0.0239(3) Uani 1 1 d . . . . .
H3A_2 H 0.184630 0.775360 0.309130 0.029 Uiso 1 1 calc R U . . .
H3AB_2 H 0.235358 0.797673 0.419006 0.029 Uiso 1 1 calc R U . . .
C4_2 C 0.27115(6) 0.81147(12) 0.33277(9) 0.0223(3) Uani 1 1 d . . . . .
H4A_2 H 0.259510 0.777002 0.269309 0.027 Uiso 1 1 calc R U . . .
H4AB_2 H 0.268186 0.913197 0.329662 0.027 Uiso 1 1 calc R U . . .
C5_2 C 0.33680(5) 0.76903(11) 0.40502(8) 0.0191(2) Uani 1 1 d . . . . .
H5A_2 H 0.364347 0.802870 0.384612 0.023 Uiso 1 1 calc R U . . .
H5AB_2 H 0.349917 0.810656 0.467328 0.023 Uiso 1 1 calc R U . . .
N1_3 N 0.38239(4) 0.40645(10) 0.41182(7) 0.0167(2) Uani 1 1 d . . . . .
F1_3 F 0.57145(3) 0.28781(7) 0.35880(5) 0.02431(17) Uani 1 1 d . . . . .
C2_3 C 0.42448(5) 0.60334(11) 0.37748(8) 0.0151(2) Uani 1 1 d . . . . .
H2_3 H 0.454037 0.664328 0.430628 0.018 Uiso 1 1 calc R U . . .
F2_3 F 0.43854(3) -0.01148(7) 0.41056(5) 0.02598(18) Uani 1 1 d . . . . .
C3_3 C 0.45724(5) 0.47226(11) 0.37884(7) 0.0158(2) Uani 1 1 d . . . . .
F3_3 F 0.43055(3) 0.11609(7) 0.50940(5) 0.02354(17) Uani 1 1 d . . . . .
C4_3 C 0.50600(5) 0.44934(12) 0.36783(8) 0.0176(2) Uani 1 1 d . . . . .
H4_3 H 0.526557 0.523281 0.358769 0.021 Uiso 1 1 calc R U . . .
F4_3 F 0.35743(3) 0.10988(7) 0.36335(5) 0.02843(19) Uani 1 1 d . . . . .
C5_3 C 0.52382(5) 0.31304(12) 0.37055(8) 0.0187(2) Uani 1 1 d . . . . .
C6_3 C 0.49599(5) 0.20303(12) 0.38505(8) 0.0185(2) Uani 1 1 d . . . . .
H6_3 H 0.509310 0.111602 0.385616 0.022 Uiso 1 1 calc R U . . .
C7_3 C 0.44761(5) 0.22822(11) 0.39899(7) 0.0169(2) Uani 1 1 d . . . . .
C8_3 C 0.42827(5) 0.36329(11) 0.39621(7) 0.0154(2) Uani 1 1 d . . . . .
C9_3 C 0.41853(5) 0.11212(11) 0.41987(8) 0.0187(2) Uani 1 1 d . . . . .
C1_3 C 0.37951(5) 0.54117(11) 0.40221(7) 0.0155(2) Uani 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
C1_1 N1_1 1.4702(14) . ?
C1_1 C2_1 1.5277(16) . ?
C1_1 H1A_1 0.9900 . ?
C1_1 H1AB_1 0.9900 . ?
N1_1 C5_1 1.4638(13) . ?
N1_1 C2_3 1.4637(14) . ?
C2_1 C3_1 1.5258(16) . ?
C2_1 H2A_1 0.9900 . ?
C2_1 H2AB_1 0.9900 . ?
C3_1 C4_1 1.5279(17) . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3AB_1 0.9900 . ?
C4_1 C5_1 1.5242(15) . ?
C4_1 H4A_1 0.9900 . ?
C4_1 H4AB_1 0.9900 . ?
C5_1 H5A_1 0.9900 . ?
C5_1 H5AB_1 0.9900 . ?
C1_2 N1_2 1.4645(14) . ?
C1_2 C2_2 1.5245(16) . ?
C1_2 H1A_2 0.9900 . ?
C1_2 H1AB_2 0.9900 . ?
N1_2 C1_3 1.3391(15) . ?
N1_2 C5_2 1.4648(14) . ?
C2_2 C3_2 1.5308(17) . ?
C2_2 H2A_2 0.9900 . ?
C2_2 H2AB_2 0.9900 . ?
C3_2 C4_2 1.5256(16) . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3AB_2 0.9900 . ?
C4_2 C5_2 1.5248(16) . ?
C4_2 H4A_2 0.9900 . ?
C4_2 H4AB_2 0.9900 . ?
C5_2 H5A_2 0.9900 . ?
C5_2 H5AB_2 0.9900 . ?
N1_3 C1_3 1.3152(15) . ?
N1_3 C8_3 1.4007(14) . ?
F1_3 C5_3 1.3619(13) . ?
C2_3 C3_3 1.5206(15) . ?
C2_3 C1_3 1.5415(14) . ?
C2_3 H2_3 1.0000 . ?
F2_3 C9_3 1.3467(13) . ?
C3_3 C4_3 1.3789(15) . ?
C3_3 C8_3 1.4094(15) . ?
F3_3 C9_3 1.3507(13) . ?
C4_3 C5_3 1.3936(16) . ?
C4_3 H4_3 0.9500 . ?
F4_3 C9_3 1.3405(14) . ?
C5_3 C6_3 1.3765(17) . ?
C6_3 C7_3 1.4036(16) . ?
C6_3 H6_3 0.9500 . ?
C7_3 C8_3 1.3949(15) . ?
C7_3 C9_3 1.4919(16) . ?

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_1 C1_1 C2_1 109.56(9) . . ?
N1_1 C1_1 H1A_1 109.8 . . ?
C2_1 C1_1 H1A_1 109.8 . . ?
N1_1 C1_1 H1AB_1 109.8 . . ?
C2_1 C1_1 H1AB_1 109.8 . . ?
H1A_1 C1_1 H1AB_1 108.2 . . ?
C5_1 N1_1 C2_3 112.04(8) . . ?
C5_1 N1_1 C1_1 110.68(8) . . ?
C2_3 N1_1 C1_1 113.61(8) . . ?
C3_1 C2_1 C1_1 110.88(9) . . ?
C3_1 C2_1 H2A_1 109.5 . . ?
C1_1 C2_1 H2A_1 109.5 . . ?
C3_1 C2_1 H2AB_1 109.5 . . ?
C1_1 C2_1 H2AB_1 109.5 . . ?
H2A_1 C2_1 H2AB_1 108.1 . . ?
C2_1 C3_1 C4_1 110.32(9) . . ?
C2_1 C3_1 H3A_1 109.6 . . ?
C4_1 C3_1 H3A_1 109.6 . . ?
C2_1 C3_1 H3AB_1 109.6 . . ?
C4_1 C3_1 H3AB_1 109.6 . . ?
H3A_1 C3_1 H3AB_1 108.1 . . ?
C5_1 C4_1 C3_1 110.29(10) . . ?
C5_1 C4_1 H4A_1 109.6 . . ?
C3_1 C4_1 H4A_1 109.6 . . ?
C5_1 C4_1 H4AB_1 109.6 . . ?
C3_1 C4_1 H4AB_1 109.6 . . ?
H4A_1 C4_1 H4AB_1 108.1 . . ?
N1_1 C5_1 C4_1 110.21(9) . . ?
N1_1 C5_1 H5A_1 109.6 . . ?
C4_1 C5_1 H5A_1 109.6 . . ?
N1_1 C5_1 H5AB_1 109.6 . . ?
C4_1 C5_1 H5AB_1 109.6 . . ?
H5A_1 C5_1 H5AB_1 108.1 . . ?
N1_2 C1_2 C2_2 110.47(9) . . ?
N1_2 C1_2 H1A_2 109.6 . . ?
C2_2 C1_2 H1A_2 109.6 . . ?
N1_2 C1_2 H1AB_2 109.6 . . ?
C2_2 C1_2 H1AB_2 109.6 . . ?
H1A_2 C1_2 H1AB_2 108.1 . . ?
C1_3 N1_2 C5_2 124.49(9) . . ?
C1_3 N1_2 C1_2 120.72(9) . . ?
C5_2 N1_2 C1_2 114.69(9) . . ?
C1_2 C2_2 C3_2 112.00(10) . . ?
C1_2 C2_2 H2A_2 109.2 . . ?
C3_2 C2_2 H2A_2 109.2 . . ?
C1_2 C2_2 H2AB_2 109.2 . . ?
C3_2 C2_2 H2AB_2 109.2 . . ?
H2A_2 C2_2 H2AB_2 107.9 . . ?
C4_2 C3_2 C2_2 110.78(10) . . ?
C4_2 C3_2 H3A_2 109.5 . . ?
C2_2 C3_2 H3A_2 109.5 . . ?
C4_2 C3_2 H3AB_2 109.5 . . ?
C2_2 C3_2 H3AB_2 109.5 . . ?
H3A_2 C3_2 H3AB_2 108.1 . . ?
C5_2 C4_2 C3_2 110.78(10) . . ?
C5_2 C4_2 H4A_2 109.5 . . ?
C3_2 C4_2 H4A_2 109.5 . . ?
C5_2 C4_2 H4AB_2 109.5 . . ?
C3_2 C4_2 H4AB_2 109.5 . . ?
H4A_2 C4_2 H4AB_2 108.1 . . ?
N1_2 C5_2 C4_2 109.77(10) . . ?
N1_2 C5_2 H5A_2 109.7 . . ?
C4_2 C5_2 H5A_2 109.7 . . ?
N1_2 C5_2 H5AB_2 109.7 . . ?
C4_2 C5_2 H5AB_2 109.7 . . ?
H5A_2 C5_2 H5AB_2 108.2 . . ?
C1_3 N1_3 C8_3 105.92(9) . . ?
N1_1 C2_3 C3_3 117.76(9) . . ?
N1_1 C2_3 C1_3 112.60(9) . . ?
C3_3 C2_3 C1_3 99.04(8) . . ?
N1_1 C2_3 H2_3 109.0 . . ?
C3_3 C2_3 H2_3 109.0 . . ?
C1_3 C2_3 H2_3 109.0 . . ?
C4_3 C3_3 C8_3 121.55(10) . . ?
C4_3 C3_3 C2_3 132.06(10) . . ?
C8_3 C3_3 C2_3 106.38(9) . . ?
C3_3 C4_3 C5_3 117.14(10) . . ?
C3_3 C4_3 H4_3 121.4 . . ?
C5_3 C4_3 H4_3 121.4 . . ?
F1_3 C5_3 C6_3 118.48(10) . . ?
F1_3 C5_3 C4_3 118.17(10) . . ?
C6_3 C5_3 C4_3 123.35(10) . . ?
C5_3 C6_3 C7_3 118.89(10) . . ?
C5_3 C6_3 H6_3 120.6 . . ?
C7_3 C6_3 H6_3 120.6 . . ?
C8_3 C7_3 C6_3 119.38(10) . . ?
C8_3 C7_3 C9_3 120.27(10) . . ?
C6_3 C7_3 C9_3 120.31(10) . . ?
C7_3 C8_3 N1_3 126.60(10) . . ?
C7_3 C8_3 C3_3 119.64(10) . . ?
N1_3 C8_3 C3_3 113.73(10) . . ?
F4_3 C9_3 F2_3 106.47(9) . . ?
F4_3 C9_3 F3_3 105.89(9) . . ?
F2_3 C9_3 F3_3 105.83(9) . . ?
F4_3 C9_3 C7_3 113.36(9) . . ?
F2_3 C9_3 C7_3 112.18(9) . . ?
F3_3 C9_3 C7_3 112.54(9) . . ?
N1_3 C1_3 N1_2 122.73(10) . . ?
N1_3 C1_3 C2_3 114.81(9) . . ?
N1_2 C1_3 C2_3 122.46(10) . . ?

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
C2_1 C1_1 N1_1 C5_1 -61.92(11) . . . . ?
C2_1 C1_1 N1_1 C2_3 171.01(9) . . . . ?
N1_1 C1_1 C2_1 C3_1 57.32(12) . . . . ?
C1_1 C2_1 C3_1 C4_1 -53.45(13) . . . . ?
C2_1 C3_1 C4_1 C5_1 53.28(13) . . . . ?
C2_3 N1_1 C5_1 C4_1 -169.58(9) . . . . ?
C1_1 N1_1 C5_1 C4_1 62.50(11) . . . . ?
C3_1 C4_1 C5_1 N1_1 -57.72(12) . . . . ?
C2_2 C1_2 N1_2 C1_3 -127.28(11) . . . . ?
C2_2 C1_2 N1_2 C5_2 56.15(13) . . . . ?
N1_2 C1_2 C2_2 C3_2 -51.92(13) . . . . ?
C1_2 C2_2 C3_2 C4_2 52.25(13) . . . . ?
C2_2 C3_2 C4_2 C5_2 -54.20(13) . . . . ?
C1_3 N1_2 C5_2 C4_2 125.16(11) . . . . ?
C1_2 N1_2 C5_2 C4_2 -58.42(12) . . . . ?
C3_2 C4_2 C5_2 N1_2 56.19(13) . . . . ?
C5_1 N1_1 C2_3 C3_3 -71.08(12) . . . . ?
C1_1 N1_1 C2_3 C3_3 55.27(12) . . . . ?
C5_1 N1_1 C2_3 C1_3 174.63(8) . . . . ?
C1_1 N1_1 C2_3 C1_3 -59.02(12) . . . . ?
N1_1 C2_3 C3_3 C4_3 62.42(16) . . . . ?
C1_3 C2_3 C3_3 C4_3 -176.02(11) . . . . ?
N1_1 C2_3 C3_3 C8_3 -118.41(10) . . . . ?
C1_3 C2_3 C3_3 C8_3 3.15(10) . . . . ?
C8_3 C3_3 C4_3 C5_3 2.67(16) . . . . ?
C2_3 C3_3 C4_3 C5_3 -178.27(10) . . . . ?
C3_3 C4_3 C5_3 F1_3 179.29(9) . . . . ?
C3_3 C4_3 C5_3 C6_3 -1.10(17) . . . . ?
F1_3 C5_3 C6_3 C7_3 178.83(9) . . . . ?
C4_3 C5_3 C6_3 C7_3 -0.77(17) . . . . ?
C5_3 C6_3 C7_3 C8_3 1.09(16) . . . . ?
C5_3 C6_3 C7_3 C9_3 -176.83(10) . . . . ?
C6_3 C7_3 C8_3 N1_3 -177.65(10) . . . . ?
C9_3 C7_3 C8_3 N1_3 0.27(17) . . . . ?
C6_3 C7_3 C8_3 C3_3 0.43(16) . . . . ?
C9_3 C7_3 C8_3 C3_3 178.35(9) . . . . ?
C1_3 N1_3 C8_3 C7_3 -179.99(11) . . . . ?
C1_3 N1_3 C8_3 C3_3 1.83(12) . . . . ?
C4_3 C3_3 C8_3 C7_3 -2.39(16) . . . . ?
C2_3 C3_3 C8_3 C7_3 178.34(9) . . . . ?
C4_3 C3_3 C8_3 N1_3 175.93(10) . . . . ?
C2_3 C3_3 C8_3 N1_3 -3.35(12) . . . . ?
C8_3 C7_3 C9_3 F4_3 53.27(14) . . . . ?
C6_3 C7_3 C9_3 F4_3 -128.83(11) . . . . ?
C8_3 C7_3 C9_3 F2_3 173.91(9) . . . . ?
C6_3 C7_3 C9_3 F2_3 -8.19(14) . . . . ?
C8_3 C7_3 C9_3 F3_3 -66.87(13) . . . . ?
C6_3 C7_3 C9_3 F3_3 111.03(11) . . . . ?
C8_3 N1_3 C1_3 N1_2 -179.04(10) . . . . ?
C8_3 N1_3 C1_3 C2_3 0.52(12) . . . . ?
C5_2 N1_2 C1_3 N1_3 179.03(10) . . . . ?
C1_2 N1_2 C1_3 N1_3 2.81(16) . . . . ?
C5_2 N1_2 C1_3 C2_3 -0.50(17) . . . . ?
C1_2 N1_2 C1_3 C2_3 -176.72(10) . . . . ?
N1_1 C2_3 C1_3 N1_3 122.89(10) . . . . ?
C3_3 C2_3 C1_3 N1_3 -2.35(12) . . . . ?
N1_1 C2_3 C1_3 N1_2 -57.55(13) . . . . ?
C3_3 C2_3 C1_3 N1_2 177.21(10) . . . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.038

