# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_cmpd_3
_database_code_depnum_ccdc_archive 'CCDC 2382889'
loop_
_audit_author_name
_audit_author_address
'Yasuhide Inokuma'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-09-10 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H36 N4'
_chemical_formula_sum            'C28 H36 N4'
_chemical_formula_weight         428.61

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0906(8)
_cell_length_b                   9.1054(5)
_cell_length_c                   9.2735(5)
_cell_angle_alpha                62.149(6)
_cell_angle_beta                 61.589(7)
_cell_angle_gamma                65.472(7)
_cell_volume                     578.30(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3346
_cell_measurement_theta_min      2.5900
_cell_measurement_theta_max      30.8510

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.65680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.822
_oxdiff_exptl_absorpt_empirical_full_max 1.738
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            6420
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.612
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2429
_reflns_number_gt                2268
_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       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0464P)²+0.2646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2429
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 1.03536(12) 0.39224(12) 0.42845(13) 0.0177(2) Uani 1 1 d . . . . .
H1 H 0.983(2) 0.349(2) 0.544(2) 0.028(4) Uiso 1 1 d . . . . .
N2 N 0.48794(12) 0.73629(12) 0.42824(13) 0.0183(2) Uani 1 1 d . . . . .
C8 C 0.63402(15) 0.65096(14) 0.32635(15) 0.0185(3) Uani 1 1 d . . . . .
C1 C 1.20834(14) 0.39091(14) 0.35441(15) 0.0180(2) Uani 1 1 d . . . . .
C5 C 0.76426(15) 0.59957(14) 0.38813(15) 0.0175(2) Uani 1 1 d . . . . .
C6 C 0.69460(15) 0.65880(14) 0.53351(15) 0.0176(2) Uani 1 1 d . . . . .
C7 C 0.52365(15) 0.74213(14) 0.55436(15) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.94768(15) 0.51525(14) 0.31729(15) 0.0182(3) Uani 1 1 d . . . . .
C2 C 1.23515(15) 0.49468(16) 0.18323(15) 0.0220(3) Uani 1 1 d . . . . .
H2 H 1.343548 0.511710 0.095609 0.026 Uiso 1 1 calc R U . . .
C3 C 1.07260(15) 0.57201(16) 0.16019(15) 0.0223(3) Uani 1 1 d . . . . .
H3 H 1.053615 0.649511 0.054464 0.027 Uiso 1 1 calc R U . . .
C11 C 0.32085(15) 0.80604(15) 0.40555(16) 0.0207(3) Uani 1 1 d . . . . .
H10 H 0.228146 0.797240 0.520994 0.025 Uiso 1 1 calc R U . . .
H11 H 0.311082 0.735624 0.356764 0.025 Uiso 1 1 calc R U . . .
C12 C 0.29350(16) 0.99212(15) 0.28647(17) 0.0231(3) Uani 1 1 d . . . . .
H12 H 0.395643 1.005052 0.177905 0.028 Uiso 1 1 calc R U . . .
H13 H 0.282748 1.065668 0.344500 0.028 Uiso 1 1 calc R U . . .
C10 C 0.63542(16) 0.62376(16) 0.17944(16) 0.0233(3) Uani 1 1 d . . . . .
H4 H 0.549842 0.560065 0.223245 0.035 Uiso 1 1 calc R U . . .
H5 H 0.750354 0.558269 0.125717 0.035 Uiso 1 1 calc R U . . .
H6 H 0.606990 0.735048 0.092578 0.035 Uiso 1 1 calc R U . . .
C9 C 0.39030(15) 0.82490(16) 0.68575(16) 0.0234(3) Uani 1 1 d . . . . .
H7 H 0.442241 0.816576 0.761634 0.035 Uiso 1 1 calc R U . . .
H8 H 0.296169 0.766761 0.755935 0.035 Uiso 1 1 calc R U . . .
H9 H 0.344721 0.945868 0.626184 0.035 Uiso 1 1 calc R U . . .
C13 C 0.13202(17) 1.05244(17) 0.24080(18) 0.0275(3) Uani 1 1 d . . . . .
H14 H 0.035594 1.014589 0.348412 0.033 Uiso 1 1 calc R U . . .
H15 H 0.099832 1.179345 0.195290 0.033 Uiso 1 1 calc R U . . .
C14 C 0.1546(2) 0.9858(2) 0.1073(2) 0.0374(4) Uani 1 1 d . . . . .
H16 H 0.239405 1.034689 -0.004418 0.056 Uiso 1 1 calc R U . . .
H17 H 0.043747 1.019047 0.093090 0.056 Uiso 1 1 calc R U . . .
H18 H 0.195207 0.860491 0.147095 0.056 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 1.3816(15) . ?
N1 C4 1.3836(15) . ?
N2 C8 1.3766(15) . ?
N2 C7 1.3820(15) . ?
N2 C11 1.4606(14) . ?
C8 C5 1.3726(17) . ?
C8 C10 1.4879(16) . ?
C1 C2 1.3761(17) . ?
C1 C6 1.4715(16) 2_766 ?
C5 C6 1.4466(16) . ?
C5 C4 1.4721(16) . ?
C6 C7 1.3785(16) . ?
C7 C9 1.4886(16) . ?
C4 C3 1.3743(17) . ?
C2 C3 1.4216(17) . ?
C11 C12 1.5217(16) . ?
C12 C13 1.5299(17) . ?
C13 C14 1.516(2) . ?

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 C4 111.10(10) . . ?
C8 N2 C7 109.84(10) . . ?
C8 N2 C11 124.05(10) . . ?
C7 N2 C11 126.10(10) . . ?
C5 C8 N2 107.97(10) . . ?
C5 C8 C10 129.76(11) . . ?
N2 C8 C10 122.26(10) . . ?
C2 C1 N1 105.75(10) . . ?
C2 C1 C6 130.45(11) . 2_766 ?
N1 C1 C6 119.72(10) . 2_766 ?
C8 C5 C6 107.43(10) . . ?
C8 C5 C4 129.24(11) . . ?
C6 C5 C4 123.07(10) . . ?
C7 C6 C5 106.85(10) . . ?
C7 C6 C1 129.98(11) . 2_766 ?
C5 C6 C1 122.53(10) . 2_766 ?
C6 C7 N2 107.90(10) . . ?
C6 C7 C9 129.70(11) . . ?
N2 C7 C9 122.40(10) . . ?
C3 C4 N1 105.77(10) . . ?
C3 C4 C5 130.09(11) . . ?
N1 C4 C5 120.22(10) . . ?
C1 C2 C3 108.19(10) . . ?
C4 C3 C2 108.19(10) . . ?
N2 C11 C12 113.35(10) . . ?
C11 C12 C13 112.13(10) . . ?
C14 C13 C12 113.68(11) . . ?

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
C7 N2 C8 C5 0.71(13) . . . . ?
C11 N2 C8 C5 -178.19(10) . . . . ?
C7 N2 C8 C10 179.81(10) . . . . ?
C11 N2 C8 C10 0.91(17) . . . . ?
C4 N1 C1 C2 -9.94(13) . . . . ?
C4 N1 C1 C6 149.64(10) . . . 2_766 ?
N2 C8 C5 C6 -0.85(12) . . . . ?
C10 C8 C5 C6 -179.86(11) . . . . ?
N2 C8 C5 C4 -175.10(11) . . . . ?
C10 C8 C5 C4 5.9(2) . . . . ?
C8 C5 C6 C7 0.69(13) . . . . ?
C4 C5 C6 C7 175.38(10) . . . . ?
C8 C5 C6 C1 172.39(10) . . . 2_766 ?
C4 C5 C6 C1 -12.93(17) . . . 2_766 ?
C5 C6 C7 N2 -0.26(12) . . . . ?
C1 C6 C7 N2 -171.12(11) 2_766 . . . ?
C5 C6 C7 C9 178.77(11) . . . . ?
C1 C6 C7 C9 7.9(2) 2_766 . . . ?
C8 N2 C7 C6 -0.26(13) . . . . ?
C11 N2 C7 C6 178.61(10) . . . . ?
C8 N2 C7 C9 -179.38(10) . . . . ?
C11 N2 C7 C9 -0.51(17) . . . . ?
C1 N1 C4 C3 10.01(13) . . . . ?
C1 N1 C4 C5 -149.85(11) . . . . ?
C8 C5 C4 C3 62.20(19) . . . . ?
C6 C5 C4 C3 -111.24(15) . . . . ?
C8 C5 C4 N1 -143.47(12) . . . . ?
C6 C5 C4 N1 43.09(16) . . . . ?
N1 C1 C2 C3 5.85(13) . . . . ?
C6 C1 C2 C3 -150.69(12) 2_766 . . . ?
N1 C4 C3 C2 -5.99(13) . . . . ?
C5 C4 C3 C2 151.12(12) . . . . ?
C1 C2 C3 C4 0.09(14) . . . . ?
C8 N2 C11 C12 -92.06(13) . . . . ?
C7 N2 C11 C12 89.23(14) . . . . ?
N2 C11 C12 C13 170.45(10) . . . . ?
C11 C12 C13 C14 -75.72(15) . . . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041


####################################################################### 
# 
# 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_cmpd_10
_database_code_depnum_ccdc_archive 'CCDC 2382890'
loop_
_audit_author_name
_audit_author_address
'Yasuhide Inokuma'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-09-10 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H37 N3 O2'
_chemical_formula_sum            'C28 H37 N3 O2'
_chemical_formula_weight         447.60

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.8130(5)
_cell_length_b                   13.3344(5)
_cell_length_c                   14.2787(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.632(4)
_cell_angle_gamma                90
_cell_volume                     2438.58(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8863
_cell_measurement_theta_min      2.0970
_cell_measurement_theta_max      30.4530

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_correction_T_min  0.56654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.652
_oxdiff_exptl_absorpt_empirical_full_max 1.437
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            20678
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.090
_diffrn_reflns_theta_max         30.730
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.785
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.785
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5970
_reflns_number_gt                5076
_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       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0582P)²+0.8654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5970
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.53750(9) 0.48233(8) 0.79907(8) 0.0188(2) Uani 1 1 d . . . . .
C2 C 0.45948(10) 0.48753(10) 0.86315(8) 0.0237(2) Uani 1 1 d . . . . .
H1 H 0.464162 0.464882 0.926208 0.028 Uiso 1 1 calc R U . . .
C3 C 0.37116(10) 0.53243(10) 0.81885(8) 0.0238(3) Uani 1 1 d . . . . .
H2 H 0.306123 0.545584 0.846731 0.029 Uiso 1 1 calc R U . . .
C4 C 0.39659(9) 0.55360(8) 0.72794(8) 0.0188(2) Uani 1 1 d . . . . .
N1 N 0.49893(7) 0.52601(7) 0.71823(7) 0.0174(2) Uani 1 1 d . . . . .
H34 H 0.534801 0.535076 0.667268 0.021 Uiso 1 1 calc R U . . .
C5 C 0.33066(8) 0.57513(9) 0.64538(8) 0.0190(2) Uani 1 1 d . . . . .
C6 C 0.26130(9) 0.65232(9) 0.63335(9) 0.0226(2) Uani 1 1 d . . . . .
N2 N 0.21196(8) 0.63976(8) 0.54632(7) 0.0225(2) Uani 1 1 d . . . . .
C7 C 0.23557(11) 0.73643(11) 0.69676(11) 0.0346(3) Uani 1 1 d . . . . .
H35 H 0.280198 0.732850 0.753547 0.052 Uiso 1 1 calc R U . . .
H36 H 0.162173 0.731655 0.713755 0.052 Uiso 1 1 calc R U . . .
H37 H 0.247351 0.800323 0.664827 0.052 Uiso 1 1 calc R U . . .
C8 C 0.13567(10) 0.70898(10) 0.50438(10) 0.0279(3) Uani 1 1 d . . . . .
H3 H 0.146326 0.711685 0.436028 0.033 Uiso 1 1 calc R U . . .
H4 H 0.149372 0.776905 0.529877 0.033 Uiso 1 1 calc R U . . .
C9 C 0.02260(10) 0.68245(10) 0.52054(10) 0.0280(3) Uani 1 1 d . . . . .
H5 H 0.008885 0.685000 0.588379 0.034 Uiso 1 1 calc R U . . .
H6 H 0.008166 0.613470 0.498035 0.034 Uiso 1 1 calc R U . . .
C10 C -0.04840(10) 0.75630(10) 0.46817(11) 0.0315(3) Uani 1 1 d . . . . .
H7 H -0.035069 0.824581 0.492975 0.038 Uiso 1 1 calc R U . . .
H8 H -0.030752 0.756233 0.401123 0.038 Uiso 1 1 calc R U . . .
C11 C -0.16295(10) 0.73237(12) 0.47643(11) 0.0340(3) Uani 1 1 d . . . . .
H9 H -0.177985 0.667333 0.447075 0.051 Uiso 1 1 calc R U . . .
H10 H -0.204714 0.784558 0.444828 0.051 Uiso 1 1 calc R U . . .
H11 H -0.180492 0.729705 0.542738 0.051 Uiso 1 1 calc R U . . .
C12 C 0.24939(9) 0.55687(9) 0.50281(8) 0.0206(2) Uani 1 1 d . . . . .
C13 C 0.20533(10) 0.52174(10) 0.41059(9) 0.0256(3) Uani 1 1 d . . . . .
H12 H 0.128936 0.525067 0.410977 0.038 Uiso 1 1 calc R U . . .
H13 H 0.227162 0.452369 0.399718 0.038 Uiso 1 1 calc R U . . .
H14 H 0.230975 0.564716 0.360544 0.038 Uiso 1 1 calc R U . . .
C14 C 0.32453(8) 0.51394(9) 0.56224(8) 0.0186(2) Uani 1 1 d . . . . .
C15 C 0.38382(8) 0.42439(9) 0.53865(8) 0.0181(2) Uani 1 1 d . . . . .
O1 O 0.40285(6) 0.40464(7) 0.45644(6) 0.02296(19) Uani 1 1 d . . . . .
C16 C 0.42239(8) 0.35137(9) 0.61372(8) 0.0186(2) Uani 1 1 d . . . . .
H15 H 0.385889 0.286351 0.605818 0.022 Uiso 1 1 calc R U . . .
H16 H 0.406868 0.378139 0.676474 0.022 Uiso 1 1 calc R U . . .
C17 C 0.54117(9) 0.33579(9) 0.60594(8) 0.0198(2) Uani 1 1 d . . . . .
H17 H 0.554490 0.299418 0.547034 0.024 Uiso 1 1 calc R U . . .
H18 H 0.575263 0.402223 0.602010 0.024 Uiso 1 1 calc R U . . .
C18 C 0.59091(9) 0.27801(9) 0.68710(9) 0.0219(2) Uani 1 1 d . . . . .
O2 O 0.58131(8) 0.18691(7) 0.68968(8) 0.0367(2) Uani 1 1 d . . . . .
C19 C 0.65574(9) 0.33238(9) 0.75747(8) 0.0194(2) Uani 1 1 d . . . . .
C20 C 0.75194(9) 0.29827(9) 0.79086(8) 0.0201(2) Uani 1 1 d . . . . .
C21 C 0.81088(10) 0.20647(9) 0.76499(9) 0.0254(3) Uani 1 1 d . . . . .
H19 H 0.875921 0.225865 0.735370 0.038 Uiso 1 1 calc R U . . .
H20 H 0.768337 0.166091 0.721086 0.038 Uiso 1 1 calc R U . . .
H21 H 0.827122 0.167082 0.821484 0.038 Uiso 1 1 calc R U . . .
N3 N 0.79072(7) 0.36751(8) 0.85360(7) 0.0201(2) Uani 1 1 d . . . . .
C22 C 0.89020(9) 0.36034(10) 0.90662(9) 0.0253(3) Uani 1 1 d . . . . .
H22 H 0.914479 0.289876 0.905620 0.030 Uiso 1 1 calc R U . . .
H23 H 0.878534 0.378669 0.972692 0.030 Uiso 1 1 calc R U . . .
C23 C 0.97575(10) 0.42762(11) 0.86858(10) 0.0316(3) Uani 1 1 d . . . . .
H24 H 0.950888 0.497912 0.868602 0.038 Uiso 1 1 calc R U . . .
H25 H 1.037841 0.423651 0.911289 0.038 Uiso 1 1 calc R U . . .
C24 C 1.00781(11) 0.40071(12) 0.77089(11) 0.0365(3) Uani 1 1 d . . . . .
H26 H 0.944848 0.397944 0.729146 0.044 Uiso 1 1 calc R U . . .
H27 H 1.039922 0.333173 0.771906 0.044 Uiso 1 1 calc R U . . .
C25 C 1.08503(13) 0.47555(14) 0.73122(13) 0.0493(4) Uani 1 1 d . . . . .
H28 H 1.053551 0.542528 0.729719 0.074 Uiso 1 1 calc R U . . .
H29 H 1.102477 0.455470 0.667521 0.074 Uiso 1 1 calc R U . . .
H30 H 1.148677 0.476717 0.770929 0.074 Uiso 1 1 calc R U . . .
C26 C 0.71976(9) 0.44478(9) 0.86296(8) 0.0198(2) Uani 1 1 d . . . . .
C27 C 0.73544(10) 0.52715(10) 0.93235(9) 0.0253(3) Uani 1 1 d . . . . .
H31 H 0.674801 0.571960 0.929821 0.038 Uiso 1 1 calc R U . . .
H32 H 0.798350 0.565105 0.917518 0.038 Uiso 1 1 calc R U . . .
H33 H 0.743497 0.498609 0.995391 0.038 Uiso 1 1 calc R U . . .
C28 C 0.63632(9) 0.42691(9) 0.80311(8) 0.0188(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3724(14) . ?
C1 C2 1.3759(16) . ?
C1 C28 1.4658(15) . ?
C2 C3 1.4137(17) . ?
C3 C4 1.3766(16) . ?
C4 N1 1.3727(14) . ?
C4 C5 1.4590(16) . ?
C5 C6 1.3674(16) . ?
C5 C14 1.4408(16) . ?
C6 N2 1.3882(16) . ?
C6 C7 1.4844(18) . ?
N2 C12 1.3618(16) . ?
N2 C8 1.4603(15) . ?
C8 C9 1.5154(18) . ?
C9 C10 1.5224(18) . ?
C10 C11 1.5098(19) . ?
C12 C14 1.3885(16) . ?
C12 C13 1.4933(17) . ?
C14 C15 1.4598(16) . ?
C15 O1 1.2342(14) . ?
C15 C16 1.5202(16) . ?
C16 C17 1.5431(15) . ?
C17 C18 1.5168(16) . ?
C18 O2 1.2216(15) . ?
C18 C19 1.4757(16) . ?
C19 C20 1.3857(16) . ?
C19 C28 1.4439(16) . ?
C20 N3 1.3699(15) . ?
C20 C21 1.4903(16) . ?
N3 C26 1.3832(15) . ?
N3 C22 1.4670(15) . ?
C22 C23 1.5281(18) . ?
C23 C24 1.509(2) . ?
C24 C25 1.526(2) . ?
C26 C28 1.3704(16) . ?
C26 C27 1.4890(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 106.67(10) . . ?
N1 C1 C28 122.48(10) . . ?
C2 C1 C28 129.97(11) . . ?
C1 C2 C3 108.14(10) . . ?
C4 C3 C2 107.50(11) . . ?
N1 C4 C3 107.02(10) . . ?
N1 C4 C5 120.26(10) . . ?
C3 C4 C5 130.92(10) . . ?
C1 N1 C4 110.54(9) . . ?
C6 C5 C14 107.62(10) . . ?
C6 C5 C4 127.51(11) . . ?
C14 C5 C4 124.82(10) . . ?
C5 C6 N2 107.43(11) . . ?
C5 C6 C7 130.31(12) . . ?
N2 C6 C7 122.25(11) . . ?
C12 N2 C6 110.42(10) . . ?
C12 N2 C8 124.48(11) . . ?
C6 N2 C8 124.98(11) . . ?
N2 C8 C9 114.94(11) . . ?
C8 C9 C10 109.56(11) . . ?
C11 C10 C9 113.18(12) . . ?
N2 C12 C14 107.63(10) . . ?
N2 C12 C13 121.85(11) . . ?
C14 C12 C13 130.37(11) . . ?
C12 C14 C5 106.90(10) . . ?
C12 C14 C15 123.54(10) . . ?
C5 C14 C15 129.55(10) . . ?
O1 C15 C14 120.81(10) . . ?
O1 C15 C16 117.70(10) . . ?
C14 C15 C16 121.48(10) . . ?
C15 C16 C17 109.69(9) . . ?
C18 C17 C16 114.03(9) . . ?
O2 C18 C19 121.55(11) . . ?
O2 C18 C17 119.19(11) . . ?
C19 C18 C17 119.13(10) . . ?
C20 C19 C28 107.11(10) . . ?
C20 C19 C18 123.44(11) . . ?
C28 C19 C18 129.44(10) . . ?
N3 C20 C19 107.84(10) . . ?
N3 C20 C21 122.60(10) . . ?
C19 C20 C21 129.52(11) . . ?
C20 N3 C26 109.76(9) . . ?
C20 N3 C22 125.96(10) . . ?
C26 N3 C22 124.23(10) . . ?
N3 C22 C23 113.56(10) . . ?
C24 C23 C22 113.96(12) . . ?
C23 C24 C25 112.60(13) . . ?
C28 C26 N3 108.27(10) . . ?
C28 C26 C27 129.15(11) . . ?
N3 C26 C27 122.49(10) . . ?
C26 C28 C19 106.97(10) . . ?
C26 C28 C1 126.48(11) . . ?
C19 C28 C1 125.61(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.85(14) . . . . ?
C28 C1 C2 C3 -167.39(12) . . . . ?
C1 C2 C3 C4 0.27(14) . . . . ?
C2 C3 C4 N1 -2.29(14) . . . . ?
C2 C3 C4 C5 162.04(12) . . . . ?
C2 C1 N1 C4 -3.38(13) . . . . ?
C28 C1 N1 C4 166.86(10) . . . . ?
C3 C4 N1 C1 3.56(13) . . . . ?
C5 C4 N1 C1 -162.78(10) . . . . ?
N1 C4 C5 C6 -137.04(12) . . . . ?
C3 C4 C5 C6 60.35(19) . . . . ?
N1 C4 C5 C14 45.98(16) . . . . ?
C3 C4 C5 C14 -116.63(15) . . . . ?
C14 C5 C6 N2 0.79(13) . . . . ?
C4 C5 C6 N2 -176.62(11) . . . . ?
C14 C5 C6 C7 179.72(13) . . . . ?
C4 C5 C6 C7 2.3(2) . . . . ?
C5 C6 N2 C12 -0.58(13) . . . . ?
C7 C6 N2 C12 -179.62(12) . . . . ?
C5 C6 N2 C8 -176.84(11) . . . . ?
C7 C6 N2 C8 4.13(19) . . . . ?
C12 N2 C8 C9 89.38(15) . . . . ?
C6 N2 C8 C9 -94.88(15) . . . . ?
N2 C8 C9 C10 -176.36(11) . . . . ?
C8 C9 C10 C11 177.12(12) . . . . ?
C6 N2 C12 C14 0.12(13) . . . . ?
C8 N2 C12 C14 176.40(11) . . . . ?
C6 N2 C12 C13 176.08(11) . . . . ?
C8 N2 C12 C13 -7.64(17) . . . . ?
N2 C12 C14 C5 0.37(12) . . . . ?
C13 C12 C14 C5 -175.13(11) . . . . ?
N2 C12 C14 C15 -178.74(10) . . . . ?
C13 C12 C14 C15 5.77(19) . . . . ?
C6 C5 C14 C12 -0.72(13) . . . . ?
C4 C5 C14 C12 176.77(10) . . . . ?
C6 C5 C14 C15 178.31(11) . . . . ?
C4 C5 C14 C15 -4.20(19) . . . . ?
C12 C14 C15 O1 29.35(16) . . . . ?
C5 C14 C15 O1 -149.54(12) . . . . ?
C12 C14 C15 C16 -149.46(11) . . . . ?
C5 C14 C15 C16 31.66(17) . . . . ?
O1 C15 C16 C17 55.20(13) . . . . ?
C14 C15 C16 C17 -125.96(11) . . . . ?
C15 C16 C17 C18 170.41(10) . . . . ?
C16 C17 C18 O2 77.89(15) . . . . ?
C16 C17 C18 C19 -106.30(12) . . . . ?
O2 C18 C19 C20 41.12(18) . . . . ?
C17 C18 C19 C20 -134.59(12) . . . . ?
O2 C18 C19 C28 -139.88(13) . . . . ?
C17 C18 C19 C28 44.41(17) . . . . ?
C28 C19 C20 N3 -0.16(13) . . . . ?
C18 C19 C20 N3 179.03(10) . . . . ?
C28 C19 C20 C21 -177.88(11) . . . . ?
C18 C19 C20 C21 1.3(2) . . . . ?
C19 C20 N3 C26 1.45(13) . . . . ?
C21 C20 N3 C26 179.37(10) . . . . ?
C19 C20 N3 C22 179.06(11) . . . . ?
C21 C20 N3 C22 -3.02(18) . . . . ?
C20 N3 C22 C23 103.96(14) . . . . ?
C26 N3 C22 C23 -78.76(15) . . . . ?
N3 C22 C23 C24 -63.90(15) . . . . ?
C22 C23 C24 C25 174.13(12) . . . . ?
C20 N3 C26 C28 -2.23(13) . . . . ?
C22 N3 C26 C28 -179.89(10) . . . . ?
C20 N3 C26 C27 174.60(11) . . . . ?
C22 N3 C26 C27 -3.06(17) . . . . ?
N3 C26 C28 C19 2.06(12) . . . . ?
C27 C26 C28 C19 -174.49(11) . . . . ?
N3 C26 C28 C1 171.36(10) . . . . ?
C27 C26 C28 C1 -5.2(2) . . . . ?
C20 C19 C28 C26 -1.19(13) . . . . ?
C18 C19 C28 C26 179.69(12) . . . . ?
C20 C19 C28 C1 -170.61(11) . . . . ?
C18 C19 C28 C1 10.27(19) . . . . ?
N1 C1 C28 C26 124.82(13) . . . . ?
C2 C1 C28 C26 -67.41(18) . . . . ?
N1 C1 C28 C19 -67.79(16) . . . . ?
C2 C1 C28 C19 99.98(16) . . . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045



