# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_pelle152
_database_code_depnum_ccdc_archive 'CCDC 1993284'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_audit_creation_date             2018-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 N6'
_chemical_formula_sum            'C19 H28 N6'
_chemical_formula_weight         340.47
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0070 '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 0.0241 0.0137 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   14.6085(5)
_cell_length_b                   12.2750(4)
_cell_length_c                   10.4746(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1878.30(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5739
_cell_measurement_temperature    150
_cell_measurement_theta_max      49.852
_cell_measurement_theta_min      3.133
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_correction_T_min  0.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 45309 reflections, Rint = 0.1364
 (19850 with I > 3sig(I), Rint = 0.0978)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15250
_diffrn_reflns_point_group_measured_fraction_full 0.531
_diffrn_reflns_point_group_measured_fraction_max 0.529
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.076
_diffrn_reflns_theta_min         3.132
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                1570
_reflns_number_total             1836
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;       
SAINT (2013) V8.38A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;       
SAINT (2013) V8.38A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
As the sample is twinned, no Flack 
parameter value is reported 
;
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         1836
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0795
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1278P)²+0.1134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.2022
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?


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 0.5553(3) 0.4175(3) 0.4098(4) 0.0430(10) Uani 1 1 d . . . . .
N2 N 0.6222(3) 0.5872(3) 0.4741(4) 0.0388(9) Uani 1 1 d . . . . .
N3 N 0.7043(3) 0.4208(3) 0.5063(4) 0.0445(10) Uani 1 1 d . . . . .
N4 N 0.6398(3) 0.2601(3) 0.4389(5) 0.0509(11) Uani 1 1 d . . . . .
N5 N 0.4791(3) 0.5793(3) 0.3795(4) 0.0418(10) Uani 1 1 d . . . . .
N6 N 0.7630(3) 0.5861(3) 0.5717(4) 0.0410(9) Uani 1 1 d . . . . .
C1 C 0.6333(3) 0.3694(4) 0.4514(4) 0.0400(11) Uani 1 1 d . . . . .
C2 C 0.5552(3) 0.5263(4) 0.4234(5) 0.0377(10) Uani 1 1 d . . . . .
C3 C 0.6950(3) 0.5291(4) 0.5155(4) 0.0369(10) Uani 1 1 d . . . . .
C4 C 0.5722(4) 0.1989(4) 0.3678(8) 0.0652(16) Uani 1 1 d . . . . .
H4A H 0.518892 0.245149 0.351128 0.098 Uiso 1 1 calc GR . . . .
H4B H 0.553292 0.135148 0.417636 0.098 Uiso 1 1 calc GR . . . .
H4C H 0.598728 0.174857 0.286634 0.098 Uiso 1 1 calc GR . . . .
C5 C 0.7229(4) 0.2037(4) 0.4779(7) 0.0628(16) Uani 1 1 d . . . . .
H5A H 0.766551 0.203040 0.406937 0.094 Uiso 1 1 calc GR . . . .
H5B H 0.707895 0.128600 0.502018 0.094 Uiso 1 1 calc GR . . . .
H5C H 0.750087 0.241376 0.551148 0.094 Uiso 1 1 calc GR . . . .
C6 C 0.4096(3) 0.5155(4) 0.3100(5) 0.0517(13) Uani 1 1 d . . . . .
H6A H 0.431612 0.499972 0.223524 0.078 Uiso 1 1 calc GR . . . .
H6B H 0.352521 0.557317 0.305126 0.078 Uiso 1 1 calc GR . . . .
H6C H 0.398380 0.446877 0.355140 0.078 Uiso 1 1 calc GR . . . .
C7 C 0.8361(3) 0.5261(5) 0.6368(6) 0.0533(14) Uani 1 1 d . . . . .
H7A H 0.834382 0.542544 0.728350 0.080 Uiso 1 1 calc GR . . . .
H7B H 0.895505 0.547839 0.601713 0.080 Uiso 1 1 calc GR . . . .
H7C H 0.827214 0.447691 0.624011 0.080 Uiso 1 1 calc GR . . . .
C8 C 0.4705(3) 0.6937(4) 0.3800(5) 0.0402(11) Uani 1 1 d . . . . .
C9 C 0.4435(3) 0.7482(4) 0.2697(5) 0.0517(13) Uani 1 1 d . . . . .
H9 H 0.431980 0.708026 0.193861 0.062 Uiso 1 1 calc R . . . .
C10 C 0.4332(4) 0.8601(4) 0.2696(6) 0.0554(14) Uani 1 1 d . . . . .
H10 H 0.415148 0.896465 0.193589 0.066 Uiso 1 1 calc R . . . .
C11 C 0.4490(4) 0.9198(4) 0.3801(7) 0.0626(16) Uani 1 1 d . . . . .
H11 H 0.441920 0.996705 0.380083 0.075 Uiso 1 1 calc R . . . .
C12 C 0.4752(4) 0.8659(5) 0.4900(7) 0.0642(16) Uani 1 1 d . . . . .
H12 H 0.486603 0.906382 0.565595 0.077 Uiso 1 1 calc R . . . .
C13 C 0.4850(4) 0.7537(4) 0.4915(5) 0.0489(12) Uani 1 1 d . . . . .
H13 H 0.501554 0.717520 0.568281 0.059 Uiso 1 1 calc R . . . .
C14 C 0.7545(3) 0.7040(3) 0.5925(5) 0.0406(11) Uani 1 1 d . . . . .
H14 H 0.717252 0.734310 0.520643 0.049 Uiso 1 1 calc R . . . .
C15 C 0.7043(3) 0.7293(4) 0.7157(5) 0.0484(12) Uani 1 1 d . . . . .
H15A H 0.738841 0.698484 0.788520 0.058 Uiso 1 1 calc R . . . .
H15B H 0.643209 0.694384 0.713899 0.058 Uiso 1 1 calc R . . . .
C16 C 0.6929(4) 0.8522(4) 0.7348(6) 0.0569(14) Uani 1 1 d . . . . .
H16A H 0.652822 0.881792 0.666946 0.068 Uiso 1 1 calc R . . . .
H16B H 0.663054 0.866006 0.818097 0.068 Uiso 1 1 calc R . . . .
C17 C 0.7846(4) 0.9098(4) 0.7310(7) 0.0688(17) Uani 1 1 d . . . . .
H17A H 0.775066 0.989514 0.736815 0.083 Uiso 1 1 calc R . . . .
H17B H 0.822063 0.886886 0.805060 0.083 Uiso 1 1 calc R . . . .
C18 C 0.8347(4) 0.8832(4) 0.6090(6) 0.0592(15) Uani 1 1 d . . . . .
H18A H 0.895529 0.918677 0.610474 0.071 Uiso 1 1 calc R . . . .
H18B H 0.800041 0.913374 0.535873 0.071 Uiso 1 1 calc R . . . .
C19 C 0.8472(4) 0.7604(4) 0.5898(6) 0.0543(13) Uani 1 1 d . . . . .
H19A H 0.877561 0.746572 0.506791 0.065 Uiso 1 1 calc R . . . .
H19B H 0.886689 0.730596 0.658226 0.065 Uiso 1 1 calc R . . . .


_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 C1 1.355(6) . ?
N1 C2 1.343(5) . ?
N2 C2 1.341(6) . ?
N2 C3 1.352(6) . ?
N3 C1 1.343(6) . ?
N3 C3 1.341(6) . ?
N4 C1 1.352(6) . ?
N4 C4 1.446(8) . ?
N4 C5 1.456(7) . ?
N5 C2 1.368(6) . ?
N5 C6 1.475(6) . ?
N5 C8 1.410(5) . ?
N6 C3 1.350(6) . ?
N6 C7 1.465(6) . ?
N6 C14 1.469(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.391(8) . ?
C8 C13 1.397(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(8) . ?
C13 H13 0.9500 . ?
C14 H14 1.0000 . ?
C14 C15 1.516(8) . ?
C14 C19 1.522(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.530(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.516(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.508(10) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.533(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 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 C1 113.6(4) . . ?
C2 N2 C3 114.0(4) . . ?
C3 N3 C1 114.7(4) . . ?
C1 N4 C4 121.2(5) . . ?
C1 N4 C5 120.2(4) . . ?
C4 N4 C5 117.8(4) . . ?
C2 N5 C6 118.2(4) . . ?
C2 N5 C8 123.0(4) . . ?
C8 N5 C6 118.0(4) . . ?
C3 N6 C7 118.6(4) . . ?
C3 N6 C14 120.8(4) . . ?
C7 N6 C14 119.2(4) . . ?
N3 C1 N1 125.6(4) . . ?
N3 C1 N4 116.9(4) . . ?
N4 C1 N1 117.4(4) . . ?
N1 C2 N5 116.0(4) . . ?
N2 C2 N1 126.6(4) . . ?
N2 C2 N5 117.4(4) . . ?
N3 C3 N2 125.5(4) . . ?
N3 C3 N6 118.1(4) . . ?
N6 C3 N2 116.5(4) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N5 C6 H6A 109.5 . . ?
N5 C6 H6B 109.5 . . ?
N5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N6 C7 H7A 109.5 . . ?
N6 C7 H7B 109.5 . . ?
N6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N5 120.0(5) . . ?
C9 C8 C13 119.0(4) . . ?
C13 C8 N5 121.0(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(5) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(5) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(5) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(6) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 119.9(5) . . ?
C12 C13 H13 120.0 . . ?
N6 C14 H14 107.5 . . ?
N6 C14 C15 111.6(4) . . ?
N6 C14 C19 111.7(4) . . ?
C15 C14 H14 107.5 . . ?
C15 C14 C19 110.7(4) . . ?
C19 C14 H14 107.5 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C14 C15 C16 111.4(4) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 C15 111.1(4) . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 C16 110.5(5) . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C17 C18 C19 112.5(5) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C14 C19 C18 109.8(4) . . ?
C14 C19 H19A 109.7 . . ?
C14 C19 H19B 109.7 . . ?
C18 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 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
N5 C8 C9 C10 178.8(4) . . . . ?
N5 C8 C13 C12 -179.3(4) . . . . ?
N6 C14 C15 C16 -178.2(4) . . . . ?
N6 C14 C19 C18 178.8(4) . . . . ?
C1 N1 C2 N2 -1.0(7) . . . . ?
C1 N1 C2 N5 178.2(4) . . . . ?
C1 N3 C3 N2 -0.4(7) . . . . ?
C1 N3 C3 N6 178.9(4) . . . . ?
C2 N1 C1 N3 2.5(7) . . . . ?
C2 N1 C1 N4 -178.8(4) . . . . ?
C2 N2 C3 N3 1.7(7) . . . . ?
C2 N2 C3 N6 -177.6(4) . . . . ?
C2 N5 C8 C9 129.9(5) . . . . ?
C2 N5 C8 C13 -52.9(7) . . . . ?
C3 N2 C2 N1 -0.9(7) . . . . ?
C3 N2 C2 N5 179.9(4) . . . . ?
C3 N3 C1 N1 -1.9(7) . . . . ?
C3 N3 C1 N4 179.4(4) . . . . ?
C3 N6 C14 C15 85.1(5) . . . . ?
C3 N6 C14 C19 -150.3(5) . . . . ?
C4 N4 C1 N1 8.5(7) . . . . ?
C4 N4 C1 N3 -172.6(5) . . . . ?
C5 N4 C1 N1 178.0(5) . . . . ?
C5 N4 C1 N3 -3.1(7) . . . . ?
C6 N5 C2 N1 -6.3(7) . . . . ?
C6 N5 C2 N2 172.9(4) . . . . ?
C6 N5 C8 C9 -40.1(7) . . . . ?
C6 N5 C8 C13 137.2(5) . . . . ?
C7 N6 C3 N2 170.1(4) . . . . ?
C7 N6 C3 N3 -9.3(7) . . . . ?
C7 N6 C14 C15 -81.4(6) . . . . ?
C7 N6 C14 C19 43.1(6) . . . . ?
C8 N5 C2 N1 -176.3(4) . . . . ?
C8 N5 C2 N2 3.0(7) . . . . ?
C8 C9 C10 C11 -0.5(8) . . . . ?
C9 C8 C13 C12 -2.0(7) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
C10 C11 C12 C13 -0.5(9) . . . . ?
C11 C12 C13 C8 1.6(8) . . . . ?
C13 C8 C9 C10 1.5(7) . . . . ?
C14 N6 C3 N2 3.4(6) . . . . ?
C14 N6 C3 N3 -175.9(4) . . . . ?
C14 C15 C16 C17 -56.0(6) . . . . ?
C15 C14 C19 C18 -56.1(6) . . . . ?
C15 C16 C17 C18 54.8(7) . . . . ?
C16 C17 C18 C19 -56.0(7) . . . . ?
C17 C18 C19 C14 56.6(6) . . . . ?
C19 C14 C15 C16 56.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pell12
_database_code_depnum_ccdc_archive 'CCDC 1993286'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H31 N5 O'
_chemical_formula_sum            'C18 H31 N5 O'
_chemical_formula_weight         333.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0140 0.0070 '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 0.0240 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   14.7113(3)
_cell_length_b                   10.5414(2)
_cell_length_c                   24.3585(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3777.46(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.678
_cell_measurement_theta_min      3.158
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1251 before and 0.0451 after correction. The Ratio of minimum to maximum transmission is 0.9287. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1456
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crysallized from MeOH'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            30234
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.647
_diffrn_reflns_theta_min         3.157
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4124
_reflns_number_total             4341
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0276(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0703P)²+0.7981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.37835(5) 0.56050(7) 0.29255(3) 0.01924(18) Uani 1 1 d . . . . .
C1 C 0.35700(6) 0.54416(9) 0.18479(4) 0.0227(2) Uani 1 1 d . . . . .
C2 C 0.44081(6) 0.50695(8) 0.25976(4) 0.01848(19) Uani 1 1 d . . . . .
N2 N 0.43431(5) 0.49809(8) 0.20405(3) 0.02223(19) Uani 1 1 d . . . . .
N3 N 0.28885(5) 0.59807(8) 0.21193(3) 0.02458(19) Uani 1 1 d . . . . .
C3 C 0.30402(6) 0.60449(8) 0.26666(4) 0.0201(2) Uani 1 1 d . . . . .
C4 C 0.58931(6) 0.40665(10) 0.25064(4) 0.0275(2) Uani 1 1 d . . . . .
H4A H 0.583894 0.314119 0.248548 0.041 Uiso 1 1 calc GR . . . .
H4B H 0.647590 0.429104 0.267531 0.041 Uiso 1 1 calc GR . . . .
H4C H 0.586268 0.442601 0.213580 0.041 Uiso 1 1 calc GR . . . .
N4 N 0.51523(5) 0.45740(7) 0.28373(3) 0.02049(18) Uani 1 1 d . . . . .
N5 N 0.23928(5) 0.65945(8) 0.29819(3) 0.02371(19) Uani 1 1 d . . . . .
C5 C 0.16498(7) 0.73028(11) 0.27266(4) 0.0326(2) Uani 1 1 d . . . . .
H5A H 0.176279 0.738022 0.233151 0.049 Uiso 1 1 calc GR . . . .
H5B H 0.161322 0.815031 0.289044 0.049 Uiso 1 1 calc GR . . . .
H5C H 0.107561 0.685246 0.278674 0.049 Uiso 1 1 calc GR . . . .
C6 C 0.52412(6) 0.45983(8) 0.34401(4) 0.0200(2) Uani 1 1 d . . . . .
H6 H 0.461243 0.460716 0.359610 0.024 Uiso 1 1 calc R . . . .
C7 C 0.57150(7) 0.34120(9) 0.36598(4) 0.0254(2) Uani 1 1 d . . . . .
H7A H 0.634478 0.337332 0.351760 0.030 Uiso 1 1 calc R . . . .
H7B H 0.538784 0.264481 0.353367 0.030 Uiso 1 1 calc R . . . .
C8 C 0.57292(7) 0.34496(10) 0.42883(4) 0.0302(2) Uani 1 1 d . . . . .
H8A H 0.509824 0.342239 0.442905 0.036 Uiso 1 1 calc R . . . .
H8B H 0.605441 0.269478 0.442931 0.036 Uiso 1 1 calc R . . . .
C9 C 0.61979(7) 0.46496(10) 0.44959(4) 0.0321(2) Uani 1 1 d . . . . .
H9A H 0.617167 0.467130 0.490189 0.038 Uiso 1 1 calc R . . . .
H9B H 0.684542 0.463597 0.438537 0.038 Uiso 1 1 calc R . . . .
C10 C 0.57443(8) 0.58363(10) 0.42648(4) 0.0313(2) Uani 1 1 d . . . . .
H10A H 0.608382 0.659633 0.438712 0.038 Uiso 1 1 calc R . . . .
H10B H 0.511686 0.589948 0.440926 0.038 Uiso 1 1 calc R . . . .
C11 C 0.57167(7) 0.58042(9) 0.36369(4) 0.0250(2) Uani 1 1 d . . . . .
H11A H 0.538692 0.655761 0.349829 0.030 Uiso 1 1 calc R . . . .
H11B H 0.634390 0.582992 0.348994 0.030 Uiso 1 1 calc R . . . .
C12 C 0.25293(6) 0.67011(9) 0.35791(4) 0.0219(2) Uani 1 1 d . . . . .
H12 H 0.289460 0.594854 0.369649 0.026 Uiso 1 1 calc R . . . .
C13 C 0.30766(7) 0.78843(9) 0.37300(4) 0.0270(2) Uani 1 1 d . . . . .
H13A H 0.366711 0.786965 0.353523 0.032 Uiso 1 1 calc R . . . .
H13B H 0.274142 0.865147 0.361183 0.032 Uiso 1 1 calc R . . . .
C14 C 0.32417(8) 0.79410(10) 0.43494(4) 0.0319(2) Uani 1 1 d . . . . .
H14A H 0.363689 0.722490 0.445975 0.038 Uiso 1 1 calc R . . . .
H14B H 0.356106 0.874003 0.444112 0.038 Uiso 1 1 calc R . . . .
C15 C 0.23510(8) 0.78751(11) 0.46687(4) 0.0376(3) Uani 1 1 d . . . . .
H15A H 0.248291 0.785485 0.506714 0.045 Uiso 1 1 calc R . . . .
H15B H 0.198583 0.864378 0.459185 0.045 Uiso 1 1 calc R . . . .
C16 C 0.18067(8) 0.67000(11) 0.45110(5) 0.0354(3) Uani 1 1 d . . . . .
H16A H 0.121864 0.670557 0.470861 0.042 Uiso 1 1 calc R . . . .
H16B H 0.214477 0.593090 0.462380 0.042 Uiso 1 1 calc R . . . .
C17 C 0.16314(7) 0.66530(10) 0.38931(4) 0.0299(2) Uani 1 1 d . . . . .
H17A H 0.130277 0.586220 0.379998 0.036 Uiso 1 1 calc R . . . .
H17B H 0.124592 0.738054 0.378425 0.036 Uiso 1 1 calc R . . . .
O18 O 0.34150(5) 0.53769(7) 0.13031(3) 0.03120(19) Uani 1 1 d . . . . .
C19 C 0.40991(9) 0.47698(13) 0.09749(4) 0.0401(3) Uani 1 1 d . . . . .
H19A H 0.390134 0.474927 0.059080 0.060 Uiso 1 1 calc GR . . . .
H19B H 0.419301 0.390101 0.110640 0.060 Uiso 1 1 calc GR . . . .
H19C H 0.466985 0.524462 0.100342 0.060 Uiso 1 1 calc GR . . . .


_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 1.3419(11) . ?
N1 C3 1.3448(11) . ?
C1 N2 1.3227(12) . ?
C1 N3 1.3286(12) . ?
C1 O18 1.3483(11) . ?
C2 N2 1.3636(11) . ?
C2 N4 1.3462(11) . ?
N3 C3 1.3534(11) . ?
C3 N5 1.3537(11) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 N4 1.4572(11) . ?
N4 C6 1.4745(10) . ?
N5 C5 1.4625(12) . ?
N5 C12 1.4728(11) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C7 1.5283(12) . ?
C6 C11 1.5281(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5314(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5268(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5255(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5305(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C13 1.5294(13) . ?
C12 C17 1.5273(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5293(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5254(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5243(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5278(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O18 C19 1.4358(14) . ?
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
C2 N1 C3 115.01(7) . . ?
N2 C1 N3 129.02(8) . . ?
N2 C1 O18 118.42(8) . . ?
N3 C1 O18 112.56(8) . . ?
N1 C2 N2 124.97(8) . . ?
N1 C2 N4 117.52(8) . . ?
N4 C2 N2 117.51(8) . . ?
C1 N2 C2 112.83(8) . . ?
C1 N3 C3 112.77(8) . . ?
N1 C3 N3 125.37(8) . . ?
N1 C3 N5 116.97(8) . . ?
N3 C3 N5 117.66(8) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
C2 N4 C4 120.72(7) . . ?
C2 N4 C6 119.82(7) . . ?
C4 N4 C6 119.40(7) . . ?
C3 N5 C5 120.20(8) . . ?
C3 N5 C12 119.81(7) . . ?
C5 N5 C12 118.87(8) . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6 107.2 . . ?
N4 C6 C7 112.02(7) . . ?
N4 C6 C11 111.55(7) . . ?
C7 C6 H6 107.2 . . ?
C11 C6 H6 107.2 . . ?
C11 C6 C7 111.23(8) . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C6 C7 C8 109.57(8) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.02(8) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.08(8) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 111.23(8) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C6 C11 C10 110.12(8) . . ?
C6 C11 H11A 109.6 . . ?
C6 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
N5 C12 H12 107.2 . . ?
N5 C12 C13 111.81(7) . . ?
N5 C12 C17 111.98(8) . . ?
C13 C12 H12 107.2 . . ?
C17 C12 H12 107.2 . . ?
C17 C12 C13 111.22(8) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 C12 110.65(8) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.40(9) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.09(9) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C15 C16 C17 111.30(9) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C12 C17 C16 110.27(8) . . ?
C12 C17 H17A 109.6 . . ?
C12 C17 H17B 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C1 O18 C19 116.88(8) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19B 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
N1 C2 N2 C1 -2.44(12) . . . . ?
N1 C2 N4 C4 -175.14(8) . . . . ?
N1 C2 N4 C6 1.93(12) . . . . ?
N1 C3 N5 C5 168.58(8) . . . . ?
N1 C3 N5 C12 0.77(12) . . . . ?
C1 N3 C3 N1 -1.00(12) . . . . ?
C1 N3 C3 N5 179.10(8) . . . . ?
C2 N1 C3 N3 0.19(12) . . . . ?
C2 N1 C3 N5 -179.91(8) . . . . ?
C2 N4 C6 C7 144.37(8) . . . . ?
C2 N4 C6 C11 -90.21(9) . . . . ?
N2 C1 N3 C3 0.05(14) . . . . ?
N2 C1 O18 C19 1.89(13) . . . . ?
N2 C2 N4 C4 5.33(12) . . . . ?
N2 C2 N4 C6 -177.60(7) . . . . ?
N3 C1 N2 C2 1.53(14) . . . . ?
N3 C1 O18 C19 -177.94(9) . . . . ?
N3 C3 N5 C5 -11.51(13) . . . . ?
N3 C3 N5 C12 -179.32(8) . . . . ?
C3 N1 C2 N2 1.69(12) . . . . ?
C3 N1 C2 N4 -177.80(7) . . . . ?
C3 N5 C12 C13 85.04(10) . . . . ?
C3 N5 C12 C17 -149.37(8) . . . . ?
C4 N4 C6 C7 -38.52(11) . . . . ?
C4 N4 C6 C11 86.90(10) . . . . ?
N4 C2 N2 C1 177.05(8) . . . . ?
N4 C6 C7 C8 -176.18(7) . . . . ?
N4 C6 C11 C10 176.49(7) . . . . ?
N5 C12 C13 C14 -177.63(8) . . . . ?
N5 C12 C17 C16 177.19(8) . . . . ?
C5 N5 C12 C13 -82.93(11) . . . . ?
C5 N5 C12 C17 42.66(11) . . . . ?
C6 C7 C8 C9 -57.23(11) . . . . ?
C7 C6 C11 C10 -57.65(10) . . . . ?
C7 C8 C9 C10 56.36(12) . . . . ?
C8 C9 C10 C11 -55.59(12) . . . . ?
C9 C10 C11 C6 55.89(11) . . . . ?
C11 C6 C7 C8 58.22(10) . . . . ?
C12 C13 C14 C15 -55.34(11) . . . . ?
C13 C12 C17 C16 -56.90(11) . . . . ?
C13 C14 C15 C16 55.26(12) . . . . ?
C14 C15 C16 C17 -55.97(12) . . . . ?
C15 C16 C17 C12 56.62(11) . . . . ?
C17 C12 C13 C14 56.37(11) . . . . ?
O18 C1 N2 C2 -178.26(8) . . . . ?
O18 C1 N3 C3 179.85(7) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Cryoloop'
_olex2_submission_original_sample_id 'AI-2 / MeOH'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pell11
_database_code_depnum_ccdc_archive 'CCDC 1993285'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H34 N6'
_chemical_formula_sum            'C19 H34 N6'
_chemical_formula_weight         346.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0140 0.0070 '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 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.7373(3)
_cell_length_b                   30.1441(16)
_cell_length_c                   6.1322(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.223(3)
_cell_angle_gamma                90
_cell_volume                     1001.41(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4757
_cell_measurement_temperature    150
_cell_measurement_theta_max      53.053
_cell_measurement_theta_min      2.551
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1510 before and 0.0779 after correction. The Ratio of minimum to maximum transmission is 0.7297. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             380
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crystallized from MeOH'
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12348
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.850
_diffrn_reflns_theta_min         2.550
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1244
_reflns_number_total             1861
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1861
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0768
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1330P)²+0.2033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2351
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.494(9)
 0.506(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.6438(6) 0.250000 0.3274(5) 0.0418(8) Uani 1 2 d S T P . .
C1 C 0.7204(5) 0.29087(9) 0.2465(5) 0.0460(7) Uani 1 1 d . . . . .
H1A H 0.673890 0.316145 0.323882 0.069 Uiso 1 1 calc GR . . . .
H1B H 0.639184 0.293473 0.079213 0.069 Uiso 1 1 calc GR . . . .
H1C H 0.899816 0.290623 0.281540 0.069 Uiso 1 1 calc GR . . . .
N2 N 0.4373(4) 0.28983(6) 0.5266(3) 0.0390(6) Uani 1 1 d . . . . .
C2 C 0.5006(6) 0.250000 0.4630(5) 0.0366(8) Uani 1 2 d S T P . .
N3 N 0.2244(5) 0.250000 0.7417(5) 0.0403(8) Uani 1 2 d S T P . .
C3 C 0.3008(5) 0.28736(8) 0.6672(4) 0.0381(6) Uani 1 1 d . . . . .
C4 C 0.0679(6) 0.32496(9) 0.8790(5) 0.0523(8) Uani 1 1 d . . . . .
H4A H -0.060985 0.302627 0.816284 0.078 Uiso 1 1 calc GR . . . .
H4B H -0.008682 0.354111 0.876230 0.078 Uiso 1 1 calc GR . . . .
H4C H 0.164322 0.317223 1.038460 0.078 Uiso 1 1 calc GR . . . .
N4 N 0.2299(4) 0.32633(7) 0.7392(4) 0.0434(6) Uani 1 1 d . . . . .
C5 C 0.3132(5) 0.36912(8) 0.6801(4) 0.0460(7) Uani 1 1 d . . . . .
H5 H 0.444565 0.362672 0.610535 0.055 Uiso 1 1 calc R . . . .
C6 C 0.1112(6) 0.39396(10) 0.4996(5) 0.0608(9) Uani 1 1 d . . . . .
H6A H -0.028931 0.398786 0.557304 0.073 Uiso 1 1 calc R . . . .
H6B H 0.051292 0.375693 0.357910 0.073 Uiso 1 1 calc R . . . .
C7 C 0.1992(8) 0.43845(11) 0.4405(6) 0.0749(10) Uani 1 1 d . . . . .
H7A H 0.058600 0.454417 0.330273 0.090 Uiso 1 1 calc R . . . .
H7B H 0.325374 0.433593 0.365120 0.090 Uiso 1 1 calc R . . . .
C8 C 0.3084(7) 0.46654(10) 0.6560(6) 0.0705(10) Uani 1 1 d . . . . .
H8A H 0.369668 0.494910 0.614161 0.085 Uiso 1 1 calc R . . . .
H8B H 0.179137 0.473368 0.725247 0.085 Uiso 1 1 calc R . . . .
C9 C 0.5191(7) 0.44190(11) 0.8299(6) 0.0738(10) Uani 1 1 d . . . . .
H9A H 0.586453 0.460176 0.970850 0.089 Uiso 1 1 calc R . . . .
H9B H 0.652841 0.436875 0.763889 0.089 Uiso 1 1 calc R . . . .
C10 C 0.4320(7) 0.39749(10) 0.8932(5) 0.0653(9) Uani 1 1 d . . . . .
H10A H 0.574517 0.381383 0.999881 0.078 Uiso 1 1 calc R . . . .
H10B H 0.311186 0.402722 0.974303 0.078 Uiso 1 1 calc R . . . .


_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 C1 1.449(3) 4_565 ?
N1 C1 1.449(3) . ?
N1 C2 1.347(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 C2 1.349(2) . ?
N2 C3 1.344(3) . ?
N3 C3 1.342(3) 4_565 ?
N3 C3 1.342(3) . ?
C3 N4 1.363(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 N4 1.458(3) . ?
N4 C5 1.462(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.511(4) . ?
C5 C10 1.522(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.518(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.517(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 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 N1 C1 116.4(3) . 4_565 ?
C2 N1 C1 121.77(14) . . ?
C2 N1 C1 121.76(14) . 4_565 ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N2 C2 113.9(2) . . ?
N1 C2 N2 117.10(15) . 4_565 ?
N1 C2 N2 117.10(15) . . ?
N2 C2 N2 125.8(3) . 4_565 ?
C3 N3 C3 114.1(3) . 4_565 ?
N2 C3 N4 117.3(2) . . ?
N3 C3 N2 126.1(2) . . ?
N3 C3 N4 116.5(2) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
C3 N4 C4 118.8(2) . . ?
C3 N4 C5 121.5(2) . . ?
C4 N4 C5 119.6(2) . . ?
N4 C5 H5 106.7 . . ?
N4 C5 C6 112.6(2) . . ?
N4 C5 C10 111.9(2) . . ?
C6 C5 H5 106.7 . . ?
C6 C5 C10 111.7(2) . . ?
C10 C5 H5 106.7 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C5 C6 C7 112.2(3) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C8 111.0(3) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 110.1(3) . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 C10 110.9(3) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C5 C10 C9 111.5(3) . . ?
C5 C10 H10A 109.3 . . ?
C5 C10 H10B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C2 N2 -2.0(5) . . . . ?
C1 N1 C2 N2 179.2(3) . . . 4_565 ?
C1 N1 C2 N2 2.0(5) 4_565 . . 4_565 ?
C1 N1 C2 N2 -179.2(3) 4_565 . . . ?
N2 C3 N4 C4 175.9(2) . . . . ?
N2 C3 N4 C5 -4.3(4) . . . . ?
C2 N2 C3 N3 -1.0(4) . . . . ?
C2 N2 C3 N4 179.9(2) . . . . ?
N3 C3 N4 C4 -3.3(4) . . . . ?
N3 C3 N4 C5 176.5(2) . . . . ?
C3 N2 C2 N1 -178.1(3) . . . . ?
C3 N2 C2 N2 0.5(5) . . . 4_565 ?
C3 N3 C3 N2 1.3(5) 4_565 . . . ?
C3 N3 C3 N4 -179.52(16) 4_565 . . . ?
C3 N4 C5 C6 106.8(3) . . . . ?
C3 N4 C5 C10 -126.5(3) . . . . ?
C4 N4 C5 C6 -73.4(3) . . . . ?
C4 N4 C5 C10 53.4(3) . . . . ?
N4 C5 C6 C7 179.7(2) . . . . ?
N4 C5 C10 C9 179.7(2) . . . . ?
C5 C6 C7 C8 -55.2(4) . . . . ?
C6 C5 C10 C9 -53.0(4) . . . . ?
C6 C7 C8 C9 57.3(4) . . . . ?
C7 C8 C9 C10 -57.9(4) . . . . ?
C8 C9 C10 C5 55.9(4) . . . . ?
C10 C5 C6 C7 52.8(3) . . . . ?

_olex2_date_sample_submission    2017-10-18
_olex2_exptl_crystal_mounting_method 'mounted on a Cryoloop'
_olex2_submission_original_sample_id AI-7/MeOH
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.494(9)
2 0.506(9)

####################################################################### 
# 
# 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_pell10
_database_code_depnum_ccdc_archive 'CCDC 1993287'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2020-03-27 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H33 N5'
_chemical_formula_sum            'C19 H33 N5'
_chemical_formula_weight         331.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0140 0.0070 '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 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   15.0700(3)
_cell_length_b                   10.3551(2)
_cell_length_c                   24.4042(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3808.31(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.647
_cell_measurement_theta_min      3.152
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1355 before and 0.0590 after correction. The Ratio of minimum to maximum transmission is 0.8516. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1456
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crystallized frommeOH'
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.088
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            34870
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.665
_diffrn_reflns_theta_min         3.151
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3894
_reflns_number_total             4386
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0067(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²+1.0642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1173
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C18(H18A,H18B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.38400(5) 0.45487(8) 0.70734(3) 0.01885(19) Uani 1 1 d . . . . .
N3 N 0.30114(6) 0.42936(9) 0.79045(4) 0.0234(2) Uani 1 1 d . . . . .
N2 N 0.44410(6) 0.52841(9) 0.79290(3) 0.0221(2) Uani 1 1 d . . . . .
N4 N 0.52019(5) 0.55489(9) 0.71116(3) 0.0207(2) Uani 1 1 d . . . . .
N5 N 0.24753(6) 0.35597(9) 0.70673(4) 0.0229(2) Uani 1 1 d . . . . .
C1 C 0.36925(7) 0.48696(10) 0.81566(4) 0.0222(2) Uani 1 1 d . . . . .
C2 C 0.44757(6) 0.51120(9) 0.73759(4) 0.0182(2) Uani 1 1 d . . . . .
C3 C 0.31270(6) 0.41490(9) 0.73556(4) 0.0193(2) Uani 1 1 d . . . . .
C4 C 0.59509(7) 0.60749(12) 0.74178(4) 0.0265(2) Uani 1 1 d . . . . .
H4A H 0.590190 0.701795 0.743319 0.040 Uiso 1 1 calc GR . . . .
H4B H 0.650619 0.583594 0.723512 0.040 Uiso 1 1 calc GR . . . .
H4C H 0.594753 0.572420 0.779078 0.040 Uiso 1 1 calc GR . . . .
C5 C 0.17759(8) 0.28460(12) 0.73510(5) 0.0310(3) Uani 1 1 d . . . . .
H5A H 0.189862 0.283821 0.774536 0.047 Uiso 1 1 calc GR . . . .
H5B H 0.175764 0.195699 0.721373 0.047 Uiso 1 1 calc GR . . . .
H5C H 0.120270 0.326413 0.728418 0.047 Uiso 1 1 calc GR . . . .
C6 C 0.52693(6) 0.54434(10) 0.65126(4) 0.0195(2) Uani 1 1 d . . . . .
H6 H 0.465190 0.535901 0.636681 0.023 Uiso 1 1 calc R . . . .
C7 C 0.56731(7) 0.66547(10) 0.62557(4) 0.0243(2) Uani 1 1 d . . . . .
H7A H 0.629364 0.675849 0.638140 0.029 Uiso 1 1 calc R . . . .
H7B H 0.533303 0.742551 0.637187 0.029 Uiso 1 1 calc R . . . .
C8 C 0.56508(8) 0.65369(11) 0.56305(4) 0.0284(2) Uani 1 1 d . . . . .
H8A H 0.502675 0.649698 0.550478 0.034 Uiso 1 1 calc R . . . .
H8B H 0.592911 0.730995 0.546490 0.034 Uiso 1 1 calc R . . . .
C9 C 0.61435(8) 0.53266(12) 0.54402(4) 0.0288(3) Uani 1 1 d . . . . .
H9A H 0.608666 0.524375 0.503755 0.035 Uiso 1 1 calc R . . . .
H9B H 0.678182 0.541437 0.552854 0.035 Uiso 1 1 calc R . . . .
C10 C 0.57793(8) 0.41131(11) 0.57127(4) 0.0295(3) Uani 1 1 d . . . . .
H10A H 0.614594 0.336190 0.560452 0.035 Uiso 1 1 calc R . . . .
H10B H 0.516602 0.395801 0.558308 0.035 Uiso 1 1 calc R . . . .
C11 C 0.57781(7) 0.42339(11) 0.63386(4) 0.0246(2) Uani 1 1 d . . . . .
H11A H 0.549671 0.346060 0.650197 0.030 Uiso 1 1 calc R . . . .
H11B H 0.639637 0.428451 0.647401 0.030 Uiso 1 1 calc R . . . .
C12 C 0.25708(7) 0.33976(10) 0.64700(4) 0.0212(2) Uani 1 1 d . . . . .
H12 H 0.290291 0.416609 0.633033 0.025 Uiso 1 1 calc R . . . .
C13 C 0.31168(7) 0.22012(10) 0.63231(4) 0.0239(2) Uani 1 1 d . . . . .
H13A H 0.281015 0.141776 0.645805 0.029 Uiso 1 1 calc R . . . .
H13B H 0.370376 0.225015 0.650409 0.029 Uiso 1 1 calc R . . . .
C14 C 0.32424(8) 0.21063(12) 0.57021(5) 0.0289(2) Uani 1 1 d . . . . .
H14A H 0.360869 0.284095 0.557460 0.035 Uiso 1 1 calc R . . . .
H14B H 0.356318 0.129852 0.561350 0.035 Uiso 1 1 calc R . . . .
C15 C 0.23558(9) 0.21197(13) 0.54017(5) 0.0354(3) Uani 1 1 d . . . . .
H15A H 0.246240 0.212490 0.500143 0.042 Uiso 1 1 calc R . . . .
H15B H 0.202014 0.132641 0.549291 0.042 Uiso 1 1 calc R . . . .
C16 C 0.18087(8) 0.32993(12) 0.55591(5) 0.0342(3) Uani 1 1 d . . . . .
H16A H 0.122350 0.325548 0.537573 0.041 Uiso 1 1 calc R . . . .
H16B H 0.211418 0.408966 0.543052 0.041 Uiso 1 1 calc R . . . .
C17 C 0.16742(7) 0.33774(11) 0.61789(5) 0.0294(3) Uani 1 1 d . . . . .
H17A H 0.133805 0.416972 0.627087 0.035 Uiso 1 1 calc R . . . .
H17B H 0.132552 0.262350 0.630492 0.035 Uiso 1 1 calc R . . . .
C18 C 0.35698(8) 0.51096(13) 0.87674(4) 0.0301(3) Uani 1 1 d . . . . .
H18A H 0.316924 0.585927 0.881417 0.036 Uiso 1 1 calc R . . . .
H18B H 0.326976 0.434878 0.892873 0.036 Uiso 1 1 calc R . . . .
C19 C 0.44074(9) 0.53621(14) 0.90868(5) 0.0351(3) Uani 1 1 d . . . . .
H19A H 0.470554 0.612705 0.893838 0.053 Uiso 1 1 calc GR . . . .
H19B H 0.480240 0.461364 0.905701 0.053 Uiso 1 1 calc GR . . . .
H19C H 0.425910 0.551007 0.947268 0.053 Uiso 1 1 calc GR . . . .


_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 1.3427(12) . ?
N1 C3 1.3417(12) . ?
N3 C1 1.3371(14) . ?
N3 C3 1.3590(13) . ?
N2 C1 1.3286(13) . ?
N2 C2 1.3624(12) . ?
N4 C2 1.3485(13) . ?
N4 C4 1.4591(12) . ?
N4 C6 1.4694(12) . ?
N5 C3 1.3535(13) . ?
N5 C5 1.4617(13) . ?
N5 C12 1.4742(13) . ?
C1 C18 1.5223(14) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C7 1.5285(14) . ?
C6 C11 1.5287(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5312(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5290(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5240(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5325(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C13 1.5299(14) . ?
C12 C17 1.5266(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5306(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5241(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5229(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5284(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5064(17) . ?
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
C3 N1 C2 115.03(9) . . ?
C1 N3 C3 113.85(9) . . ?
C1 N2 C2 113.86(9) . . ?
C2 N4 C4 120.54(8) . . ?
C2 N4 C6 120.46(8) . . ?
C4 N4 C6 118.93(8) . . ?
C3 N5 C5 120.33(9) . . ?
C3 N5 C12 119.64(8) . . ?
C5 N5 C12 118.76(8) . . ?
N3 C1 C18 115.47(9) . . ?
N2 C1 N3 127.11(9) . . ?
N2 C1 C18 117.37(9) . . ?
N1 C2 N2 125.04(9) . . ?
N1 C2 N4 117.50(8) . . ?
N4 C2 N2 117.46(9) . . ?
N1 C3 N3 125.07(9) . . ?
N1 C3 N5 116.96(9) . . ?
N5 C3 N3 117.97(9) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6 107.2 . . ?
N4 C6 C7 112.00(8) . . ?
N4 C6 C11 111.84(8) . . ?
C7 C6 H6 107.2 . . ?
C7 C6 C11 111.02(8) . . ?
C11 C6 H6 107.2 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C6 C7 C8 109.55(9) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 110.94(9) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.61(9) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C9 C10 C11 111.60(9) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C6 C11 C10 110.15(9) . . ?
C6 C11 H11A 109.6 . . ?
C6 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N5 C12 H12 107.2 . . ?
N5 C12 C13 112.11(8) . . ?
N5 C12 C17 112.04(9) . . ?
C13 C12 H12 107.2 . . ?
C17 C12 H12 107.2 . . ?
C17 C12 C13 110.85(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 C14 110.52(9) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.54(10) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.14(9) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C15 C16 C17 111.34(10) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C12 C17 C16 110.11(9) . . ?
C12 C17 H17A 109.6 . . ?
C12 C17 H17B 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
C1 C18 H18A 108.4 . . ?
C1 C18 H18B 108.4 . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 C1 115.67(9) . . ?
C19 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 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
N3 C1 C18 C19 161.69(11) . . . . ?
N2 C1 C18 C19 -20.38(15) . . . . ?
N4 C6 C7 C8 -175.05(8) . . . . ?
N4 C6 C11 C10 176.22(8) . . . . ?
N5 C12 C13 C14 -177.00(8) . . . . ?
N5 C12 C17 C16 176.21(9) . . . . ?
C1 N3 C3 N1 -0.99(14) . . . . ?
C1 N3 C3 N5 179.16(9) . . . . ?
C1 N2 C2 N1 -1.77(14) . . . . ?
C1 N2 C2 N4 177.76(9) . . . . ?
C2 N1 C3 N3 1.02(14) . . . . ?
C2 N1 C3 N5 -179.13(9) . . . . ?
C2 N2 C1 N3 1.84(16) . . . . ?
C2 N2 C1 C18 -175.81(9) . . . . ?
C2 N4 C6 C7 139.16(10) . . . . ?
C2 N4 C6 C11 -95.48(11) . . . . ?
C3 N1 C2 N2 0.47(14) . . . . ?
C3 N1 C2 N4 -179.06(9) . . . . ?
C3 N3 C1 N2 -0.58(16) . . . . ?
C3 N3 C1 C18 177.11(9) . . . . ?
C3 N5 C12 C13 83.62(11) . . . . ?
C3 N5 C12 C17 -151.01(9) . . . . ?
C4 N4 C2 N1 -174.93(9) . . . . ?
C4 N4 C2 N2 5.50(14) . . . . ?
C4 N4 C6 C7 -43.83(12) . . . . ?
C4 N4 C6 C11 81.52(11) . . . . ?
C5 N5 C3 N1 166.36(9) . . . . ?
C5 N5 C3 N3 -13.77(14) . . . . ?
C5 N5 C12 C13 -83.51(11) . . . . ?
C5 N5 C12 C17 41.86(13) . . . . ?
C6 N4 C2 N1 2.02(14) . . . . ?
C6 N4 C2 N2 -177.55(9) . . . . ?
C6 C7 C8 C9 -57.40(12) . . . . ?
C7 C6 C11 C10 -57.89(11) . . . . ?
C7 C8 C9 C10 55.41(12) . . . . ?
C8 C9 C10 C11 -54.18(13) . . . . ?
C9 C10 C11 C6 55.02(12) . . . . ?
C11 C6 C7 C8 59.15(11) . . . . ?
C12 N5 C3 N1 -0.57(14) . . . . ?
C12 N5 C3 N3 179.30(9) . . . . ?
C12 C13 C14 C15 -55.38(12) . . . . ?
C13 C12 C17 C16 -57.73(12) . . . . ?
C13 C14 C15 C16 54.76(13) . . . . ?
C14 C15 C16 C17 -55.64(13) . . . . ?
C15 C16 C17 C12 57.04(12) . . . . ?
C17 C12 C13 C14 56.98(12) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id OL-VI-119/MeOH
_olex2_submission_special_instructions 'No special instructions were received'
