# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Mezei_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2090886'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University, Department of Chemistry
United States of America
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-08-18 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         ?
_chemical_formula_sum            'C10 H14 N4'
_chemical_formula_weight         190.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.5321(3)
_cell_length_b                   8.0983(3)
_cell_length_c                   9.2836(4)
_cell_angle_alpha                71.4315(18)
_cell_angle_beta                 73.3773(17)
_cell_angle_gamma                66.8118(19)
_cell_volume                     484.97(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3428
_cell_measurement_theta_min      5.1136
_cell_measurement_theta_max      78.7672

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.660
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            4616
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.113
_diffrn_reflns_theta_max         78.756
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             1952
_reflns_number_gt                1780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1172 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+0.1693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1952
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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 0.67011(18) 0.81024(18) 0.96981(14) 0.0262(3) Uani 1 1 d . . . . .
H1N H 0.674(3) 0.887(3) 1.022(2) 0.031 Uiso 1 1 d . U . . .
N2 N 0.49633(17) 0.82861(17) 0.93923(14) 0.0253(3) Uani 1 1 d . . . . .
N3 N -0.06731(18) 0.84308(18) 0.14635(14) 0.0280(3) Uani 1 1 d . . . . .
N4 N 0.09930(18) 0.84682(18) 0.17137(14) 0.0252(3) Uani 1 1 d . . . . .
H4N H 0.192(3) 0.872(3) 0.093(2) 0.030 Uiso 1 1 d . U . . .
C1 C 0.8222(2) 0.6867(2) 0.90191(17) 0.0265(3) Uani 1 1 d . . . . .
H1 H 0.956656 0.653360 0.906415 0.032 Uiso 1 1 calc R U . . .
C2 C 0.7474(2) 0.6176(2) 0.82475(16) 0.0254(3) Uani 1 1 d . . . . .
H2 H 0.818236 0.526722 0.766086 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5433(2) 0.70998(19) 0.85103(15) 0.0221(3) Uani 1 1 d . . . . .
C4 C 0.3878(2) 0.6930(2) 0.79202(16) 0.0254(3) Uani 1 1 d . . . . .
H4A H 0.258230 0.776684 0.831748 0.030 Uiso 1 1 calc R U . . .
H4B H 0.385198 0.564996 0.832139 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4212(2) 0.7404(2) 0.61488(16) 0.0245(3) Uani 1 1 d . . . . .
H5A H 0.435366 0.864267 0.574325 0.029 Uiso 1 1 calc R U . . .
H5B H 0.545198 0.649871 0.575435 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2535(2) 0.7390(2) 0.55538(16) 0.0251(3) Uani 1 1 d . . . . .
H6A H 0.128452 0.823404 0.600592 0.030 Uiso 1 1 calc R U . . .
H6B H 0.244925 0.612955 0.590759 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2781(2) 0.7978(2) 0.37887(16) 0.0262(3) Uani 1 1 d . . . . .
H7A H 0.291738 0.921900 0.342840 0.031 Uiso 1 1 calc R U . . .
H7B H 0.400134 0.710378 0.333429 0.031 Uiso 1 1 calc R U . . .
C8 C 0.1082(2) 0.80281(19) 0.32297(16) 0.0226(3) Uani 1 1 d . . . . .
C9 C -0.0631(2) 0.7673(2) 0.40199(17) 0.0277(3) Uani 1 1 d . . . . .
H9 H -0.103279 0.732018 0.510771 0.033 Uiso 1 1 calc R U . . .
C10 C -0.1649(2) 0.7945(2) 0.28729(17) 0.0291(4) Uani 1 1 d . . . . .
H10 H -0.289605 0.779947 0.307967 0.035 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 C1 1.340(2) . ?
N1 N2 1.3595(16) . ?
N1 H1N 0.91(2) . ?
N2 C3 1.3365(19) . ?
N3 C10 1.325(2) . ?
N3 N4 1.3531(16) . ?
N4 C8 1.3520(18) . ?
N4 H4N 0.886(19) . ?
C1 C2 1.371(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.4066(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.4939(18) . ?
C4 C5 1.5338(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5216(19) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5314(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.4947(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.379(2) . ?
C9 C10 1.398(2) . ?
C9 H9 0.9500 . ?
C10 H10 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
C1 N1 N2 112.01(12) . . ?
C1 N1 H1N 127.6(12) . . ?
N2 N1 H1N 120.0(12) . . ?
C3 N2 N1 104.94(12) . . ?
C10 N3 N4 103.85(11) . . ?
C8 N4 N3 113.23(12) . . ?
C8 N4 H4N 125.6(12) . . ?
N3 N4 H4N 121.1(12) . . ?
N1 C1 C2 107.21(12) . . ?
N1 C1 H1 126.4 . . ?
C2 C1 H1 126.4 . . ?
C1 C2 C3 105.23(13) . . ?
C1 C2 H2 127.4 . . ?
C3 C2 H2 127.4 . . ?
N2 C3 C2 110.61(12) . . ?
N2 C3 C4 120.47(13) . . ?
C2 C3 C4 128.91(13) . . ?
C3 C4 C5 112.58(11) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 112.35(11) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 113.07(12) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 112.29(12) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N4 C8 C9 105.70(12) . . ?
N4 C8 C7 122.91(12) . . ?
C9 C8 C7 131.40(12) . . ?
C8 C9 C10 105.05(13) . . ?
C8 C9 H9 127.5 . . ?
C10 C9 H9 127.5 . . ?
N3 C10 C9 112.17(13) . . ?
N3 C10 H10 123.9 . . ?
C9 C10 H10 123.9 . . ?

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 N2 C3 0.88(16) . . . . ?
C10 N3 N4 C8 -0.18(17) . . . . ?
N2 N1 C1 C2 -0.91(16) . . . . ?
N1 C1 C2 C3 0.55(16) . . . . ?
N1 N2 C3 C2 -0.50(16) . . . . ?
N1 N2 C3 C4 -179.19(12) . . . . ?
C1 C2 C3 N2 -0.03(16) . . . . ?
C1 C2 C3 C4 178.53(13) . . . . ?
N2 C3 C4 C5 119.52(14) . . . . ?
C2 C3 C4 C5 -58.9(2) . . . . ?
C3 C4 C5 C6 -175.09(12) . . . . ?
C4 C5 C6 C7 176.40(12) . . . . ?
C5 C6 C7 C8 -177.72(12) . . . . ?
N3 N4 C8 C9 0.26(17) . . . . ?
N3 N4 C8 C7 -179.96(13) . . . . ?
C6 C7 C8 N4 -178.48(13) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
N4 C8 C9 C10 -0.22(17) . . . . ?
C7 C8 C9 C10 -179.97(15) . . . . ?
N4 N3 C10 C9 0.03(18) . . . . ?
C8 C9 C10 N3 0.12(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N N2 0.91(2) 2.243(19) 2.9863(18) 138.2(16) 2_677 yes
N1 H1N N3 0.91(2) 2.394(19) 3.0356(17) 127.4(15) 1_656 yes
N4 H4N N2 0.886(19) 2.287(19) 3.1268(18) 158.2(16) 1_554 yes

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pentane, Chloroform'
####################################################################### 
# 
# 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_Mezei11_0m
_database_code_depnum_ccdc_archive 'CCDC 2090887'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University, Department of Chemistry
United States of America
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-08-18 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         ?
_chemical_formula_sum            'C20 H30 N4 O2'
_chemical_formula_weight         358.48

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'
O O 0.0106 0.0060 '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                   16.5743(11)
_cell_length_b                   4.6460(3)
_cell_length_c                   12.7547(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.570(3)
_cell_angle_gamma                90
_cell_volume                     973.61(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6558
_cell_measurement_theta_min      2.4794
_cell_measurement_theta_max      33.1626

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            21842
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.297
_diffrn_reflns_theta_max         33.217
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3653
_reflns_number_gt                2575
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Apex3 v2019.11-0 (Bruker, 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1231(Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The tetrahydropyrane was refined as disordered by a slight rotation. 
The two disordered moieties were restrained to have similar geometries. 
Uij components of ADPs for disordered atoms closer to each other than 
2.0 Angstrom were restrained to be similar. Subject to these conditions 
the occupancy ratio refined to 0.585(11) to 0.451(11). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+0.0939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3653
_refine_ls_number_parameters     164
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.26109(5) 0.3786(2) 0.14758(7) 0.0444(2) Uani 1 1 d . . . . .
N2 N 0.27874(4) 0.56816(17) 0.07210(6) 0.03408(17) Uani 1 1 d . . . . .
C1 C 0.48304(5) 0.9045(2) 0.04013(7) 0.0366(2) Uani 1 1 d . . . . .
H1A H 0.491516 0.999101 0.110271 0.044 Uiso 1 1 calc R U . . .
H1B H 0.513098 0.719866 0.045881 0.044 Uiso 1 1 calc R U . . .
C2 C 0.39254(5) 0.8446(2) 0.00966(7) 0.0361(2) Uani 1 1 d . . . . .
H2A H 0.362431 1.029043 0.006884 0.043 Uiso 1 1 calc R U . . .
H2B H 0.383985 0.758811 -0.062000 0.043 Uiso 1 1 calc R U . . .
C3 C 0.35848(5) 0.64649(19) 0.08492(7) 0.03367(19) Uani 1 1 d . . . . .
C4 C 0.39408(6) 0.5040(2) 0.17396(7) 0.0421(2) Uani 1 1 d . . . . .
H4 H 0.449401 0.512854 0.204844 0.050 Uiso 1 1 calc R U . . .
C5 C 0.33160(7) 0.3438(2) 0.20916(8) 0.0470(2) Uani 1 1 d . . . . .
H5 H 0.338670 0.223980 0.270022 0.056 Uiso 1 1 calc R U . . .
C6 C 0.21744(5) 0.65964(19) -0.01221(6) 0.03232(18) Uani 0.585(11) 1 d D U P A
1
H6 H 0.225933 0.868536 -0.026151 0.039 Uiso 0.585(11) 1 calc R U P A 1
C7 C 0.1309(2) 0.6186(12) 0.0119(3) 0.0433(8) Uani 0.585(11) 1 d D U P A 1
H7A H 0.122070 0.733510 0.074769 0.052 Uiso 0.585(11) 1 calc R U P A 1
H7B H 0.121345 0.413481 0.027246 0.052 Uiso 0.585(11) 1 calc R U P A 1
C8 C 0.0718(3) 0.7161(13) -0.0840(4) 0.0508(11) Uani 0.585(11) 1 d D U P A 1
H8A H 0.015647 0.662192 -0.073664 0.061 Uiso 0.585(11) 1 calc R U P A 1
H8B H 0.074103 0.928270 -0.090302 0.061 Uiso 0.585(11) 1 calc R U P A 1
C9 C 0.0929(3) 0.5788(13) -0.1858(4) 0.0498(8) Uani 0.585(11) 1 d D U P A 1
H9A H 0.079263 0.371304 -0.186125 0.060 Uiso 0.585(11) 1 calc R U P A 1
H9B H 0.059930 0.669527 -0.247404 0.060 Uiso 0.585(11) 1 calc R U P A 1
C10 C 0.1822(2) 0.6149(11) -0.1953(3) 0.0457(7) Uani 0.585(11) 1 d D U P A 1
H10A H 0.195170 0.513654 -0.259304 0.055 Uiso 0.585(11) 1 calc R U P A 1
H10B H 0.194660 0.821745 -0.202867 0.055 Uiso 0.585(11) 1 calc R U P A 1
O1 O 0.2317(2) 0.5005(11) -0.1033(3) 0.0390(6) Uani 0.585(11) 1 d D U P A 1
C6B C 0.21744(5) 0.65964(19) -0.01221(6) 0.03232(18) Uani 0.415(11) 1 d D . P A
2
H6B H 0.235769 0.844175 -0.041795 0.039 Uiso 0.415(11) 1 calc R U P A 2
C7B C 0.1360(4) 0.7090(16) 0.0237(5) 0.0492(13) Uani 0.415(11) 1 d D . P A 2
H7C H 0.140194 0.862245 0.078065 0.059 Uiso 0.415(11) 1 calc R U P A 2
H7D H 0.117126 0.530498 0.055172 0.059 Uiso 0.415(11) 1 calc R U P A 2
C8B C 0.0755(5) 0.7985(16) -0.0723(6) 0.0480(13) Uani 0.415(11) 1 d D . P A 2
H8C H 0.020238 0.813105 -0.051305 0.058 Uiso 0.415(11) 1 calc R U P A 2
H8D H 0.090738 0.990132 -0.097374 0.058 Uiso 0.415(11) 1 calc R U P A 2
C9B C 0.0750(4) 0.5820(16) -0.1609(5) 0.0458(11) Uani 0.415(11) 1 d D . P A 2
H9C H 0.051981 0.397436 -0.139817 0.055 Uiso 0.415(11) 1 calc R U P A 2
H9D H 0.040381 0.653544 -0.224795 0.055 Uiso 0.415(11) 1 calc R U P A 2
C10B C 0.1606(4) 0.5352(16) -0.1853(4) 0.0508(12) Uani 0.415(11) 1 d D . P A 2
H10C H 0.160357 0.385598 -0.240569 0.061 Uiso 0.415(11) 1 calc R U P A 2
H10D H 0.181376 0.715848 -0.212993 0.061 Uiso 0.415(11) 1 calc R U P A 2
O1B O 0.2136(4) 0.4469(14) -0.0920(5) 0.0412(10) Uani 0.415(11) 1 d D . 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 C5 1.3292(13) . ?
N1 N2 1.3647(11) . ?
N2 C3 1.3598(11) . ?
N2 C6B 1.4426(10) . ?
N2 C6 1.4426(10) . ?
C1 C1 1.5173(19) 3_675 ?
C1 C2 1.5249(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.4932(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.3782(12) . ?
C4 C5 1.3964(16) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 O1 1.423(4) . ?
C6 C7 1.518(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.531(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.527(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.511(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O1 1.441(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6B O1B 1.414(6) . ?
C6B C7B 1.498(6) . ?
C6B H6B 1.0000 . ?
C7B C8B 1.535(9) . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C8B C9B 1.512(8) . ?
C8B H8C 0.9900 . ?
C8B H8D 0.9900 . ?
C9B C10B 1.508(6) . ?
C9B H9C 0.9900 . ?
C9B H9D 0.9900 . ?
C10B O1B 1.443(7) . ?
C10B H10C 0.9900 . ?
C10B H10D 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
C5 N1 N2 103.99(8) . . ?
C3 N2 N1 112.53(7) . . ?
C3 N2 C6B 126.07(7) . . ?
N1 N2 C6B 121.37(7) . . ?
C3 N2 C6 126.07(7) . . ?
N1 N2 C6 121.37(7) . . ?
C1 C1 C2 111.99(8) 3_675 . ?
C1 C1 H1A 109.2 3_675 . ?
C2 C1 H1A 109.2 . . ?
C1 C1 H1B 109.2 3_675 . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 113.03(7) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N2 C3 C4 105.92(8) . . ?
N2 C3 C2 122.10(7) . . ?
C4 C3 C2 131.97(8) . . ?
C3 C4 C5 105.42(8) . . ?
C3 C4 H4 127.3 . . ?
C5 C4 H4 127.3 . . ?
N1 C5 C4 112.14(9) . . ?
N1 C5 H5 123.9 . . ?
C4 C5 H5 123.9 . . ?
O1 C6 N2 106.21(18) . . ?
O1 C6 C7 111.29(19) . . ?
N2 C6 C7 113.80(17) . . ?
O1 C6 H6 108.5 . . ?
N2 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
C6 C7 C8 108.8(3) . . ?
C6 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C7 111.2(4) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 110.9(4) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O1 C10 C9 110.6(3) . . ?
O1 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C6 O1 C10 109.6(3) . . ?
O1B C6B N2 106.9(3) . . ?
O1B C6B C7B 111.7(3) . . ?
N2 C6B C7B 113.0(3) . . ?
O1B C6B H6B 108.3 . . ?
N2 C6B H6B 108.3 . . ?
C7B C6B H6B 108.3 . . ?
C6B C7B C8B 108.5(5) . . ?
C6B C7B H7C 110.0 . . ?
C8B C7B H7C 110.0 . . ?
C6B C7B H7D 110.0 . . ?
C8B C7B H7D 110.0 . . ?
H7C C7B H7D 108.4 . . ?
C9B C8B C7B 110.8(5) . . ?
C9B C8B H8C 109.5 . . ?
C7B C8B H8C 109.5 . . ?
C9B C8B H8D 109.5 . . ?
C7B C8B H8D 109.5 . . ?
H8C C8B H8D 108.1 . . ?
C10B C9B C8B 109.7(6) . . ?
C10B C9B H9C 109.7 . . ?
C8B C9B H9C 109.7 . . ?
C10B C9B H9D 109.7 . . ?
C8B C9B H9D 109.7 . . ?
H9C C9B H9D 108.2 . . ?
O1B C10B C9B 111.0(4) . . ?
O1B C10B H10C 109.4 . . ?
C9B C10B H10C 109.4 . . ?
O1B C10B H10D 109.4 . . ?
C9B C10B H10D 109.4 . . ?
H10C C10B H10D 108.0 . . ?
C6B O1B C10B 111.1(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
C5 N1 N2 C3 1.02(11) . . . . ?
C5 N1 N2 C6B 179.03(9) . . . . ?
C5 N1 N2 C6 179.03(9) . . . . ?
C1 C1 C2 C3 177.46(10) 3_675 . . . ?
N1 N2 C3 C4 -0.88(11) . . . . ?
C6B N2 C3 C4 -178.79(8) . . . . ?
C6 N2 C3 C4 -178.79(8) . . . . ?
N1 N2 C3 C2 177.93(8) . . . . ?
C6B N2 C3 C2 0.03(14) . . . . ?
C6 N2 C3 C2 0.03(14) . . . . ?
C1 C2 C3 N2 179.47(8) . . . . ?
C1 C2 C3 C4 -2.06(15) . . . . ?
N2 C3 C4 C5 0.37(11) . . . . ?
C2 C3 C4 C5 -178.28(10) . . . . ?
N2 N1 C5 C4 -0.76(13) . . . . ?
C3 C4 C5 N1 0.25(13) . . . . ?
C3 N2 C6 O1 75.8(2) . . . . ?
N1 N2 C6 O1 -101.9(2) . . . . ?
C3 N2 C6 C7 -161.4(2) . . . . ?
N1 N2 C6 C7 20.9(3) . . . . ?
O1 C6 C7 C8 -58.7(4) . . . . ?
N2 C6 C7 C8 -178.6(2) . . . . ?
C6 C7 C8 C9 50.3(4) . . . . ?
C7 C8 C9 C10 -49.7(5) . . . . ?
C8 C9 C10 O1 55.5(5) . . . . ?
N2 C6 O1 C10 -169.98(18) . . . . ?
C7 C6 O1 C10 65.7(3) . . . . ?
C9 C10 O1 C6 -63.3(4) . . . . ?
C3 N2 C6B O1B 93.9(3) . . . . ?
N1 N2 C6B O1B -83.8(3) . . . . ?
C3 N2 C6B C7B -142.7(3) . . . . ?
N1 N2 C6B C7B 39.5(3) . . . . ?
O1B C6B C7B C8B -58.1(5) . . . . ?
N2 C6B C7B C8B -178.8(3) . . . . ?
C6B C7B C8B C9B 53.6(7) . . . . ?
C7B C8B C9B C10B -53.1(8) . . . . ?
C8B C9B C10B O1B 56.0(7) . . . . ?
N2 C6B O1B C10B -173.3(3) . . . . ?
C7B C6B O1B C10B 62.5(4) . . . . ?
C9B C10B O1B C6B -60.9(5) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.033



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Heptane, Ethyl Acetate'
####################################################################### 
# 
# 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_Mezei10_0m
_database_code_depnum_ccdc_archive 'CCDC 2090888'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University, Department of Chemistry
United States of America
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-08-18 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         ?
_chemical_formula_sum            'C21 H32 N4 O2'
_chemical_formula_weight         372.50

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'
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                   8.2970(3)
_cell_length_b                   9.2575(3)
_cell_length_c                   15.0135(5)
_cell_angle_alpha                87.5026(18)
_cell_angle_beta                 80.0574(19)
_cell_angle_gamma                64.7954(17)
_cell_volume                     1027.14(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5939
_cell_measurement_theta_min      2.7537
_cell_measurement_theta_max      33.1139

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            21263
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.433
_diffrn_reflns_theta_max         33.285
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7387
_reflns_number_gt                4424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Apex3 v2019.11-0 (Bruker, 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1231(Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+0.0195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         7387
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.71556(11) 0.09472(9) 0.74231(5) 0.02797(18) Uani 1 1 d . . . . .
O2 O -0.08539(11) 0.68266(9) 0.21161(5) 0.02788(18) Uani 1 1 d . . . . .
N1 N 0.49588(13) 0.37051(11) 0.89593(6) 0.0293(2) Uani 1 1 d . . . . .
N2 N 0.47982(12) 0.31454(11) 0.81670(6) 0.02334(18) Uani 1 1 d . . . . .
N3 N -0.28432(14) 1.02929(12) 0.30449(7) 0.0315(2) Uani 1 1 d . . . . .
N4 N -0.12874(12) 0.89271(11) 0.30321(6) 0.02469(19) Uani 1 1 d . . . . .
C1 C 0.44196(16) 0.52664(13) 0.88402(8) 0.0305(2) Uani 1 1 d . . . . .
H1 H 0.437617 0.599311 0.928131 0.037 Uiso 1 1 calc R U . . .
C2 C 0.39236(16) 0.57127(13) 0.79879(8) 0.0292(2) Uani 1 1 d . . . . .
H2 H 0.349314 0.675415 0.775265 0.035 Uiso 1 1 calc R U . . .
C3 C 0.41956(14) 0.43128(13) 0.75645(7) 0.0228(2) Uani 1 1 d . . . . .
C4 C 0.39375(15) 0.39994(13) 0.66370(7) 0.0251(2) Uani 1 1 d . . . . .
H4A H 0.352331 0.313863 0.666485 0.030 Uiso 1 1 calc R U . . .
H4B H 0.511054 0.362837 0.622055 0.030 Uiso 1 1 calc R U . . .
C5 C 0.25689(17) 0.54813(14) 0.62686(8) 0.0324(3) Uani 1 1 d . . . . .
H5A H 0.292017 0.636832 0.631541 0.039 Uiso 1 1 calc R U . . .
H5B H 0.137692 0.577829 0.665939 0.039 Uiso 1 1 calc R U . . .
C6 C 0.23579(15) 0.53322(14) 0.52954(8) 0.0286(2) Uani 1 1 d . . . . .
H6A H 0.207790 0.440928 0.522596 0.034 Uiso 1 1 calc R U . . .
H6B H 0.350609 0.514210 0.488638 0.034 Uiso 1 1 calc R U . . .
C7 C 0.08422(16) 0.68545(14) 0.50367(8) 0.0308(2) Uani 1 1 d . . . . .
H7A H -0.031472 0.695556 0.540459 0.037 Uiso 1 1 calc R U . . .
H7B H 0.104788 0.777900 0.520127 0.037 Uiso 1 1 calc R U . . .
C8 C 0.06437(15) 0.69568(15) 0.40455(8) 0.0294(2) Uani 1 1 d . . . . .
H8A H 0.175595 0.694459 0.367123 0.035 Uiso 1 1 calc R U . . .
H8B H 0.049497 0.601236 0.386218 0.035 Uiso 1 1 calc R U . . .
C9 C -0.09517(15) 0.84476(14) 0.38774(7) 0.0262(2) Uani 1 1 d . . . . .
C10 C -0.23335(17) 0.95711(15) 0.44625(8) 0.0326(3) Uani 1 1 d . . . . .
H10 H -0.249123 0.959810 0.510451 0.039 Uiso 1 1 calc R U . . .
C11 C -0.34604(18) 1.06670(15) 0.39189(9) 0.0350(3) Uani 1 1 d . . . . .
H11 H -0.454007 1.157241 0.414788 0.042 Uiso 1 1 calc R U . . .
C12 C 0.54184(14) 0.14539(12) 0.79921(7) 0.0236(2) Uani 1 1 d . . . . .
H12 H 0.457304 0.129575 0.764774 0.028 Uiso 1 1 calc R U . . .
C13 C 0.55421(16) 0.04854(13) 0.88345(8) 0.0285(2) Uani 1 1 d . . . . .
H13A H 0.433823 0.085692 0.922316 0.034 Uiso 1 1 calc R U . . .
H13B H 0.638433 0.061552 0.918297 0.034 Uiso 1 1 calc R U . . .
C14 C 0.62286(18) -0.12774(14) 0.85473(8) 0.0329(3) Uani 1 1 d . . . . .
H14A H 0.642043 -0.194430 0.908695 0.040 Uiso 1 1 calc R U . . .
H14B H 0.531227 -0.142032 0.826325 0.040 Uiso 1 1 calc R U . . .
C15 C 0.79978(18) -0.18112(14) 0.78788(9) 0.0372(3) Uani 1 1 d . . . . .
H15A H 0.896811 -0.185016 0.819470 0.045 Uiso 1 1 calc R U . . .
H15B H 0.834211 -0.289920 0.763578 0.045 Uiso 1 1 calc R U . . .
C16 C 0.78101(19) -0.06758(14) 0.71080(9) 0.0358(3) Uani 1 1 d . . . . .
H16A H 0.900111 -0.099275 0.671301 0.043 Uiso 1 1 calc R U . . .
H16B H 0.696595 -0.075665 0.674152 0.043 Uiso 1 1 calc R U . . .
C17 C -0.02799(15) 0.80637(13) 0.21894(7) 0.0244(2) Uani 1 1 d . . . . .
H17 H 0.103596 0.756136 0.222987 0.029 Uiso 1 1 calc R U . . .
C18 C -0.05568(18) 0.91093(14) 0.13795(7) 0.0306(2) Uani 1 1 d . . . . .
H18A H -0.013945 0.994883 0.144310 0.037 Uiso 1 1 calc R U . . .
H18B H -0.185682 0.963558 0.133448 0.037 Uiso 1 1 calc R U . . .
C19 C 0.05235(19) 0.80649(15) 0.05280(8) 0.0348(3) Uani 1 1 d . . . . .
H19A H 0.025786 0.871380 -0.001479 0.042 Uiso 1 1 calc R U . . .
H19B H 0.183290 0.766107 0.053904 0.042 Uiso 1 1 calc R U . . .
C20 C 0.00398(18) 0.66591(15) 0.04745(8) 0.0333(3) Uani 1 1 d . . . . .
H20A H -0.121486 0.705270 0.035927 0.040 Uiso 1 1 calc R U . . .
H20B H 0.085744 0.592182 -0.003348 0.040 Uiso 1 1 calc R U . . .
C21 C 0.02113(18) 0.57792(14) 0.13483(8) 0.0328(3) Uani 1 1 d . . . . .
H21A H -0.018591 0.491668 0.131943 0.039 Uiso 1 1 calc R U . . .
H21B H 0.149594 0.527953 0.142369 0.039 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 C16 1.4334(13) . ?
O1 C12 1.4357(13) . ?
O2 C17 1.4297(12) . ?
O2 C21 1.4372(13) . ?
N1 C1 1.3325(15) . ?
N1 N2 1.3669(12) . ?
N2 C3 1.3591(14) . ?
N2 C12 1.4452(13) . ?
N3 C11 1.3268(16) . ?
N3 N4 1.3670(14) . ?
N4 C9 1.3613(14) . ?
N4 C17 1.4464(13) . ?
C1 C2 1.4029(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3812(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.5034(15) . ?
C4 C5 1.5170(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5202(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5264(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5197(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.4999(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3726(16) . ?
C10 C11 1.3976(18) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.5104(16) . ?
C12 H12 1.0000 . ?
C13 C14 1.5356(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5241(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5117(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5075(16) . ?
C17 H17 1.0000 . ?
C18 C19 1.5318(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5252(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5091(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 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
C16 O1 C12 110.74(9) . . ?
C17 O2 C21 110.58(8) . . ?
C1 N1 N2 103.81(9) . . ?
C3 N2 N1 112.79(9) . . ?
C3 N2 C12 125.85(9) . . ?
N1 N2 C12 121.01(9) . . ?
C11 N3 N4 103.93(10) . . ?
C9 N4 N3 112.59(9) . . ?
C9 N4 C17 126.40(10) . . ?
N3 N4 C17 120.72(9) . . ?
N1 C1 C2 112.18(10) . . ?
N1 C1 H1 123.9 . . ?
C2 C1 H1 123.9 . . ?
C3 C2 C1 105.20(10) . . ?
C3 C2 H2 127.4 . . ?
C1 C2 H2 127.4 . . ?
N2 C3 C2 106.01(10) . . ?
N2 C3 C4 123.10(9) . . ?
C2 C3 C4 130.89(11) . . ?
C3 C4 C5 111.82(9) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 115.73(10) . . ?
C4 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C5 C6 C7 110.26(9) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 115.81(10) . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 C8 C7 111.38(9) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N4 C9 C10 105.70(10) . . ?
N4 C9 C8 122.89(10) . . ?
C10 C9 C8 131.41(11) . . ?
C9 C10 C11 105.80(10) . . ?
C9 C10 H10 127.1 . . ?
C11 C10 H10 127.1 . . ?
N3 C11 C10 111.98(11) . . ?
N3 C11 H11 124.0 . . ?
C10 C11 H11 124.0 . . ?
O1 C12 N2 105.63(8) . . ?
O1 C12 C13 110.96(9) . . ?
N2 C12 C13 114.11(9) . . ?
O1 C12 H12 108.7 . . ?
N2 C12 H12 108.7 . . ?
C13 C12 H12 108.7 . . ?
C12 C13 C14 108.38(9) . . ?
C12 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C15 C14 C13 110.20(10) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.74(11) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O1 C16 C15 112.10(10) . . ?
O1 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
O1 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
O2 C17 N4 105.89(8) . . ?
O2 C17 C18 111.48(9) . . ?
N4 C17 C18 113.20(9) . . ?
O2 C17 H17 108.7 . . ?
N4 C17 H17 108.7 . . ?
C18 C17 H17 108.7 . . ?
C17 C18 C19 108.60(10) . . ?
C17 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C20 C19 C18 110.59(10) . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 110.17(10) . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
O2 C21 C20 111.78(10) . . ?
O2 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
O2 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?

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 N2 C3 0.63(12) . . . . ?
C1 N1 N2 C12 174.22(9) . . . . ?
C11 N3 N4 C9 0.77(13) . . . . ?
C11 N3 N4 C17 174.91(10) . . . . ?
N2 N1 C1 C2 -0.16(13) . . . . ?
N1 C1 C2 C3 -0.33(14) . . . . ?
N1 N2 C3 C2 -0.85(12) . . . . ?
C12 N2 C3 C2 -174.06(9) . . . . ?
N1 N2 C3 C4 178.87(9) . . . . ?
C12 N2 C3 C4 5.65(16) . . . . ?
C1 C2 C3 N2 0.68(12) . . . . ?
C1 C2 C3 C4 -179.00(11) . . . . ?
N2 C3 C4 C5 155.80(10) . . . . ?
C2 C3 C4 C5 -24.56(16) . . . . ?
C3 C4 C5 C6 173.89(10) . . . . ?
C4 C5 C6 C7 175.51(10) . . . . ?
C5 C6 C7 C8 172.35(10) . . . . ?
C6 C7 C8 C9 176.42(9) . . . . ?
N3 N4 C9 C10 -1.22(13) . . . . ?
C17 N4 C9 C10 -174.96(10) . . . . ?
N3 N4 C9 C8 178.18(10) . . . . ?
C17 N4 C9 C8 4.44(17) . . . . ?
C7 C8 C9 N4 171.13(10) . . . . ?
C7 C8 C9 C10 -9.64(18) . . . . ?
N4 C9 C10 C11 1.13(13) . . . . ?
C8 C9 C10 C11 -178.20(12) . . . . ?
N4 N3 C11 C10 0.00(14) . . . . ?
C9 C10 C11 N3 -0.72(15) . . . . ?
C16 O1 C12 N2 -172.62(9) . . . . ?
C16 O1 C12 C13 63.23(12) . . . . ?
C3 N2 C12 O1 73.08(12) . . . . ?
N1 N2 C12 O1 -99.62(11) . . . . ?
C3 N2 C12 C13 -164.77(10) . . . . ?
N1 N2 C12 C13 22.52(14) . . . . ?
O1 C12 C13 C14 -60.36(12) . . . . ?
N2 C12 C13 C14 -179.53(9) . . . . ?
C12 C13 C14 C15 54.40(13) . . . . ?
C13 C14 C15 C16 -51.60(14) . . . . ?
C12 O1 C16 C15 -59.44(14) . . . . ?
C14 C15 C16 O1 53.94(14) . . . . ?
C21 O2 C17 N4 -173.62(9) . . . . ?
C21 O2 C17 C18 62.86(12) . . . . ?
C9 N4 C17 O2 77.13(12) . . . . ?
N3 N4 C17 O2 -96.14(11) . . . . ?
C9 N4 C17 C18 -160.44(10) . . . . ?
N3 N4 C17 C18 26.29(14) . . . . ?
O2 C17 C18 C19 -59.08(12) . . . . ?
N4 C17 C18 C19 -178.34(9) . . . . ?
C17 C18 C19 C20 53.51(14) . . . . ?
C18 C19 C20 C21 -52.01(15) . . . . ?
C17 O2 C21 C20 -60.42(13) . . . . ?
C19 C20 C21 O2 55.13(14) . . . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Heptane, Ethyl Acetate'
