# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2008494'
loop_
_audit_author_name
_audit_author_address
'Wen-Hua Sun '
;Institute of Chemistry Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-06-08 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2020-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H21 N3'
_chemical_formula_sum            'C21 H21 N3'
_chemical_formula_weight         315.41
_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 0.0033 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   4.8540(10)
_cell_length_b                   21.542(4)
_cell_length_c                   15.408(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.60(3)
_cell_angle_gamma                90
_cell_volume                     1609.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5276
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4622
_cell_measurement_theta_min      1.3229
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9896
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.077
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22322
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.626
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3542
_reflns_number_total             3689
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0687
_refine_ls_restrained_S_all      1.152
_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)+(0.0623P)²+1.2038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1665
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C14(H14A,H14B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N2(H2), C2(H2A), C18(H18), C19(H19), C16(H16), C3(H3A),
 C5(H5), C9(H9), C17(H17), C4(H4), C11(H11), C12(H12), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.4716(3) 0.12866(8) 0.20171(10) 0.0255(4) Uani 1 1 d . . . . .
H1 H 0.367191 0.095250 0.201105 0.031 Uiso 1 1 calc R . . . .
C1 C 0.6736(4) 0.13492(9) 0.13968(12) 0.0245(4) Uani 1 1 d . . . . .
N3 N 0.6159(4) 0.06819(8) 0.36668(11) 0.0308(4) Uani 1 1 d . . . . .
H3 H 0.443056 0.068420 0.346849 0.037 Uiso 1 1 calc R . . . .
C20 C 0.6657(4) 0.17836(9) 0.33583(12) 0.0250(4) Uani 1 1 d . . . . .
C15 C 0.7507(4) 0.12437(9) 0.38176(12) 0.0256(4) Uani 1 1 d . . . . .
N2 N 0.7292(4) -0.00096(8) 0.19468(12) 0.0330(4) Uani 1 1 d . . . . .
H2 H 0.888829 0.013910 0.214426 0.040 Uiso 1 1 calc R . . . .
C2 C 0.8190(4) 0.18969(9) 0.12693(12) 0.0276(4) Uani 1 1 d . . . . .
H2A H 0.787998 0.224750 0.162594 0.033 Uiso 1 1 calc R . . . .
C13 C 0.6009(4) -0.04253(9) 0.33483(13) 0.0298(4) Uani 1 1 d . . . . .
C18 C 1.0076(4) 0.23884(10) 0.41934(13) 0.0296(4) Uani 1 1 d . . . . .
H18 H 1.091854 0.277756 0.432316 0.036 Uiso 1 1 calc R . . . .
C19 C 0.7963(4) 0.23409(9) 0.35554(12) 0.0278(4) Uani 1 1 d . . . . .
H19 H 0.739711 0.270326 0.324446 0.033 Uiso 1 1 calc R . . . .
C16 C 0.9673(4) 0.12911(10) 0.44458(13) 0.0298(4) Uani 1 1 d . . . . .
H16 H 1.029586 0.092948 0.474796 0.036 Uiso 1 1 calc R . . . .
C3 C 1.0095(4) 0.19333(10) 0.06213(13) 0.0301(4) Uani 1 1 d . . . . .
H3A H 1.110581 0.230579 0.054736 0.036 Uiso 1 1 calc R . . . .
C5 C 0.9144(4) 0.08790(10) 0.02277(13) 0.0305(4) Uani 1 1 d . . . . .
H5 H 0.946255 0.053215 -0.013499 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4345(5) -0.09162(10) 0.20131(14) 0.0363(5) Uani 1 1 d . . . . .
H9 H 0.423749 -0.093305 0.139641 0.044 Uiso 1 1 calc R . . . .
C17 C 1.0925(4) 0.18579(10) 0.46347(13) 0.0300(4) Uani 1 1 d . . . . .
H17 H 1.237334 0.188129 0.506936 0.036 Uiso 1 1 calc R . . . .
C6 C 0.7305(4) 0.08225(9) 0.08883(12) 0.0270(4) Uani 1 1 d . . . . .
C21 C 0.4317(4) 0.17643(9) 0.26697(12) 0.0271(4) Uani 1 1 d . . . . .
H21A H 0.256145 0.168512 0.295366 0.033 Uiso 1 1 calc R . . . .
H21B H 0.416851 0.217386 0.238001 0.033 Uiso 1 1 calc R . . . .
C14 C 0.7542(4) 0.00864(10) 0.38293(14) 0.0327(5) Uani 1 1 d . . . . .
H14A H 0.761942 -0.000340 0.446007 0.039 Uiso 1 1 calc R . . . .
H14B H 0.945631 0.010831 0.363531 0.039 Uiso 1 1 calc R . . . .
C4 C 1.0525(4) 0.14319(10) 0.00860(13) 0.0309(4) Uani 1 1 d . . . . .
H4 H 1.175346 0.146466 -0.037462 0.037 Uiso 1 1 calc R . . . .
C8 C 0.5886(4) -0.04486(9) 0.24311(13) 0.0294(4) Uani 1 1 d . . . . .
C11 C 0.3090(5) -0.13373(11) 0.33847(16) 0.0412(5) Uani 1 1 d . . . . .
H11 H 0.214163 -0.163822 0.370893 0.049 Uiso 1 1 calc R . . . .
C7 C 0.6084(4) 0.01995(9) 0.11103(13) 0.0299(4) Uani 1 1 d . . . . .
H7A H 0.405855 0.023681 0.114265 0.036 Uiso 1 1 calc R . . . .
H7B H 0.647706 -0.010655 0.065283 0.036 Uiso 1 1 calc R . . . .
C12 C 0.4614(5) -0.08728(10) 0.38058(15) 0.0351(5) Uani 1 1 d . . . . .
H12 H 0.470459 -0.086066 0.442279 0.042 Uiso 1 1 calc R . . . .
C10 C 0.2969(5) -0.13562(11) 0.24852(16) 0.0417(5) Uani 1 1 d . . . . .
H10 H 0.193663 -0.167297 0.219039 0.050 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 1.407(2) . ?
N1 C21 1.458(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.413(3) . ?
N3 C15 1.390(3) . ?
N3 C14 1.464(3) . ?
C20 C15 1.413(3) . ?
C20 C19 1.385(3) . ?
C20 C21 1.519(3) . ?
C15 C16 1.400(3) . ?
N2 C8 1.401(3) . ?
N2 C7 1.463(3) . ?
C2 C3 1.394(3) . ?
C13 C14 1.506(3) . ?
C13 C8 1.413(3) . ?
C13 C12 1.389(3) . ?
C18 C19 1.392(3) . ?
C18 C17 1.383(3) . ?
C16 C17 1.389(3) . ?
C3 C4 1.381(3) . ?
C5 C6 1.389(3) . ?
C5 C4 1.389(3) . ?
C9 C8 1.395(3) . ?
C9 C10 1.385(3) . ?
C6 C7 1.512(3) . ?
C11 C12 1.388(3) . ?
C11 C10 1.385(3) . ?

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 C21 121.30(16) . . ?
N1 C1 C6 117.36(17) . . ?
C2 C1 N1 123.38(18) . . ?
C2 C1 C6 119.26(18) . . ?
C15 N3 C14 121.71(16) . . ?
C15 C20 C21 121.29(17) . . ?
C19 C20 C15 118.88(17) . . ?
C19 C20 C21 119.82(17) . . ?
N3 C15 C20 120.54(17) . . ?
N3 C15 C16 120.78(18) . . ?
C16 C15 C20 118.64(18) . . ?
C8 N2 C7 119.46(17) . . ?
C1 C2 C3 120.36(19) . . ?
C8 C13 C14 121.05(18) . . ?
C12 C13 C14 119.98(19) . . ?
C12 C13 C8 118.93(19) . . ?
C17 C18 C19 118.69(19) . . ?
C20 C19 C18 122.28(19) . . ?
C17 C16 C15 121.12(19) . . ?
C4 C3 C2 120.47(19) . . ?
C6 C5 C4 121.41(19) . . ?
C10 C9 C8 120.9(2) . . ?
C18 C17 C16 120.36(18) . . ?
C1 C6 C7 119.90(17) . . ?
C5 C6 C1 118.95(18) . . ?
C5 C6 C7 120.99(18) . . ?
N1 C21 C20 112.49(15) . . ?
N3 C14 C13 110.15(16) . . ?
C3 C4 C5 119.33(19) . . ?
N2 C8 C13 120.62(19) . . ?
C9 C8 N2 120.36(19) . . ?
C9 C8 C13 119.02(19) . . ?
C10 C11 C12 119.1(2) . . ?
N2 C7 C6 109.09(17) . . ?
C11 C12 C13 121.7(2) . . ?
C9 C10 C11 120.4(2) . . ?

_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_2
_database_code_depnum_ccdc_archive 'CCDC 2008495'
loop_
_audit_author_name
_audit_author_address
'Wen-Hua Sun '
;Institute of Chemistry Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-06-08 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2020-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C35 H33 N5'
_chemical_formula_sum            'C35 H33 N5'
_chemical_formula_weight         523.69
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   18.000(4)
_cell_length_b                   7.9196(16)
_cell_length_c                   19.361(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.93(3)
_cell_angle_gamma                90
_cell_volume                     2753.4(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7552
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4737
_cell_measurement_theta_min      1.1340
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2632
_exptl_crystal_description       block
_exptl_crystal_F_000             1112.3898
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.149
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18851
_diffrn_reflns_theta_full        27.4818
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.13
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.9956
_diffrn_measurement_details      
;
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.0361
	          2theta: -19.9621
scan:
	Number of images: 270
	           Slice: -110.0000 - 25.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0361
	          2theta: -19.9621
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_number_total             6738
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0229
_diffrn_orient_matrix_UB_12      0.0413
_diffrn_orient_matrix_UB_13      0.0295
_diffrn_orient_matrix_UB_21      0.0267
_diffrn_orient_matrix_UB_22      0.0616
_diffrn_orient_matrix_UB_23      -0.1070
_diffrn_orient_matrix_UB_31      -0.0444
_diffrn_orient_matrix_UB_32      0.0264
_diffrn_orient_matrix_UB_33      0.0041
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -23
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                5377
_reflns_number_total             6284
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.4936
_refine_diff_density_min         -0.5855
_refine_diff_density_rms         0.0775
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             17.9573
_refine_ls_goodness_of_fit_ref   1.0387
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0791
_refine_ls_restrained_S_all      1.0387
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+2.5717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1746
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C35(H35a,H35b), C21(H21a,H21b), C28(H28a,H28b)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), N1(H1), C14(H14), N4(H4), C10(H10), C30(H30), C9(H9),
 C11(H11), C12(H12), C3(H3), C2(H2a), C23(H23), C33(H33), C31(H31), C5(H5a),
 C18(H18), C26(H26), C4(H4a), C16(H16), C17(H17), C19(H19), C32(H32), C24(H24),
 C25(H25)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
N2 N 0.31328(10) 0.3397(2) 0.30882(10) 0.0319(4) Uani 1.000000 .
H2 H 0.27889(10) 0.3591(2) 0.27522(10) 0.0382(5) Uiso 1.000000 R
N5 N 0.14974(10) 0.8348(2) 0.29963(10) 0.0324(4) Uani 1.000000 .
H5 H 0.17988(10) 0.8536(2) 0.33656(10) 0.0389(5) Uiso 1.000000 R
C34 C 0.25267(13) 0.8884(3) 0.22876(12) 0.0318(5) Uani 1.000000 .
C29 C 0.17492(12) 0.8729(3) 0.23484(11) 0.0288(5) Uani 1.000000 .
N1 N 0.30249(10) 0.7107(2) 0.32445(10) 0.0343(4) Uani 1.000000 .
H1 H 0.27240(10) 0.6333(2) 0.30566(10) 0.0412(5) Uiso 1.000000 R
C7 C 0.29450(13) 0.3738(3) 0.37928(12) 0.0330(5) Uani 1.000000 .
H7a H 0.24134(13) 0.4063(3) 0.37850(12) 0.0397(6) Uiso 1.000000 R
H7b H 0.30084(13) 0.2685(3) 0.40665(12) 0.0397(6) Uiso 1.000000 R
N3 N 0.28162(11) 0.3932(2) 0.17081(10) 0.0331(4) Uani 1.000000 .
C35 C 0.30703(13) 0.8753(3) 0.29136(13) 0.0357(5) Uani 1.000000 .
H35a H 0.35824(13) 0.8932(3) 0.27716(13) 0.0429(6) Uiso 1.000000 R
H35b H 0.29617(13) 0.9647(3) 0.32494(13) 0.0429(6) Uiso 1.000000 R
C14 C 0.34427(13) 0.3216(3) 0.16323(12) 0.0352(5) Uani 1.000000 .
H14 H 0.35816(13) 0.3034(3) 0.11736(12) 0.0423(6) Uiso 1.000000 R
C8 C 0.38054(12) 0.2798(3) 0.29104(12) 0.0305(5) Uani 1.000000 .
C22 C 0.09457(12) 0.4503(3) 0.29010(12) 0.0316(5) Uani 1.000000 .
N4 N 0.11198(13) 0.4825(3) 0.22351(11) 0.0424(5) Uani 1.000000 .
H4 H 0.11432(13) 0.5884(3) 0.21000(11) 0.0508(6) Uiso 1.000000 R
C10 C 0.50383(14) 0.1670(3) 0.32127(14) 0.0426(6) Uani 1.000000 .
H10 H 0.54100(14) 0.1346(3) 0.35593(14) 0.0511(7) Uiso 1.000000 R
C13 C 0.39574(12) 0.2660(3) 0.21997(12) 0.0326(5) Uani 1.000000 .
C30 C 0.12686(14) 0.8998(3) 0.17591(12) 0.0352(5) Uani 1.000000 .
H30 H 0.07454(14) 0.8937(3) 0.17942(12) 0.0423(6) Uiso 1.000000 R
C9 C 0.43660(13) 0.2295(3) 0.34105(13) 0.0361(5) Uani 1.000000 .
H9 H 0.42827(13) 0.2384(3) 0.38884(13) 0.0433(6) Uiso 1.000000 R
C21 C 0.12680(13) 0.3502(3) 0.17403(12) 0.0343(5) Uani 1.000000 .
H21a H 0.16169(13) 0.2664(3) 0.19605(12) 0.0412(6) Uiso 1.000000 R
H21b H 0.07987(13) 0.2914(3) 0.15918(12) 0.0412(6) Uiso 1.000000 R
C6 C 0.34084(12) 0.5116(3) 0.41527(12) 0.0316(5) Uani 1.000000 .
C1 C 0.34518(12) 0.6740(3) 0.38553(12) 0.0317(5) Uani 1.000000 .
C27 C 0.07772(12) 0.5853(3) 0.33449(12) 0.0320(5) Uani 1.000000 .
C15 C 0.23721(13) 0.4466(3) 0.11120(12) 0.0340(5) Uani 1.000000 .
C28 C 0.07597(12) 0.7656(3) 0.30939(12) 0.0319(5) Uani 1.000000 .
H28a H 0.05143(12) 0.8364(3) 0.34327(12) 0.0383(6) Uiso 1.000000 R
H28b H 0.04552(12) 0.7715(3) 0.26489(12) 0.0383(6) Uiso 1.000000 R
C11 C 0.51820(14) 0.1505(3) 0.25224(15) 0.0439(6) Uani 1.000000 .
H11 H 0.56433(14) 0.1061(3) 0.23948(15) 0.0527(7) Uiso 1.000000 R
C20 C 0.16010(13) 0.4272(3) 0.11226(12) 0.0337(5) Uani 1.000000 .
C12 C 0.46448(14) 0.1998(3) 0.20267(14) 0.0395(6) Uani 1.000000 .
H12 H 0.47402(14) 0.1888(3) 0.15522(14) 0.0474(7) Uiso 1.000000 R
C3 C 0.42712(14) 0.7608(4) 0.48360(14) 0.0455(6) Uani 1.000000 .
H3 H 0.45698(14) 0.8456(4) 0.50641(14) 0.0546(8) Uiso 1.000000 R
C2 C 0.38992(13) 0.7957(3) 0.41993(14) 0.0401(6) Uani 1.000000 .
H2a H 0.39502(13) 0.9039(3) 0.39955(14) 0.0482(7) Uiso 1.000000 R
C23 C 0.09217(14) 0.2843(3) 0.31497(13) 0.0391(6) Uani 1.000000 .
H23 H 0.10163(14) 0.1925(3) 0.28522(13) 0.0469(7) Uiso 1.000000 R
C33 C 0.27842(14) 0.9227(3) 0.16453(13) 0.0398(6) Uani 1.000000 .
H33 H 0.33056(14) 0.9306(3) 0.16024(13) 0.0477(7) Uiso 1.000000 R
C31 C 0.15468(15) 0.9352(3) 0.11260(13) 0.0410(6) Uani 1.000000 .
H31 H 0.12124(15) 0.9524(3) 0.07310(13) 0.0492(7) Uiso 1.000000 R
C5 C 0.37845(14) 0.4815(3) 0.47888(12) 0.0396(6) Uani 1.000000 .
H5a H 0.37494(14) 0.3730(3) 0.49926(12) 0.0475(7) Uiso 1.000000 R
C18 C 0.14592(18) 0.5602(4) 0.00002(14) 0.0531(7) Uani 1.000000 .
H18 H 0.11456(18) 0.5999(4) -0.03800(14) 0.0638(9) Uiso 1.000000 R
C26 C 0.06155(15) 0.5481(4) 0.40207(13) 0.0442(6) Uani 1.000000 .
H26 H 0.05034(15) 0.6378(4) 0.43221(13) 0.0530(7) Uiso 1.000000 R
C4 C 0.42117(15) 0.6048(4) 0.51396(14) 0.0464(7) Uani 1.000000 .
H4a H 0.44573(15) 0.5817(4) 0.55795(14) 0.0557(8) Uiso 1.000000 R
C16 C 0.26752(16) 0.5236(3) 0.05513(13) 0.0444(6) Uani 1.000000 .
H16 H 0.31989(16) 0.5384(3) 0.05498(13) 0.0533(7) Uiso 1.000000 R
C17 C 0.22161(18) 0.5787(4) -0.00042(14) 0.0521(7) Uani 1.000000 .
H17 H 0.24255(18) 0.6296(4) -0.03905(14) 0.0625(9) Uiso 1.000000 R
C19 C 0.11489(16) 0.4836(3) 0.05582(14) 0.0444(6) Uani 1.000000 .
H19 H 0.06244(16) 0.4697(3) 0.05542(14) 0.0533(7) Uiso 1.000000 R
C32 C 0.23032(16) 0.9458(3) 0.10621(14) 0.0444(6) Uani 1.000000 .
H32 H 0.24923(16) 0.9687(3) 0.06255(14) 0.0533(7) Uiso 1.000000 R
C24 C 0.07611(17) 0.2537(4) 0.38260(14) 0.0513(7) Uani 1.000000 .
H24 H 0.07525(17) 0.1407(4) 0.39898(14) 0.0615(9) Uiso 1.000000 R
C25 C 0.06134(19) 0.3838(4) 0.42662(14) 0.0570(8) Uani 1.000000 .
H25 H 0.05113(19) 0.3614(4) 0.47323(14) 0.0683(10) Uiso 1.000000 R


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
N2 C7 1.453(3) . ?
N2 C8 1.366(3) . ?
N5 C29 1.396(3) . ?
N5 C28 1.461(3) . ?
C34 C29 1.418(3) . ?
C34 C35 1.508(3) . ?
C34 C33 1.383(3) . ?
C29 C30 1.400(3) . ?
N1 C35 1.457(3) . ?
N1 C1 1.396(3) . ?
C7 C6 1.515(3) . ?
N3 C14 1.279(3) . ?
N3 C15 1.423(3) . ?
C14 C13 1.456(3) . ?
C8 C13 1.425(3) . ?
C8 C9 1.408(3) . ?
C22 N4 1.372(3) . ?
C22 C27 1.418(3) . ?
C22 C23 1.402(3) . ?
N4 C21 1.456(3) . ?
C10 C9 1.385(3) . ?
C10 C11 1.385(4) . ?
C13 C12 1.405(3) . ?
C30 C31 1.384(3) . ?
C21 C20 1.503(3) . ?
C6 C1 1.414(3) . ?
C6 C5 1.385(3) . ?
C1 C2 1.396(3) . ?
C27 C28 1.508(3) . ?
C27 C26 1.391(3) . ?
C15 C20 1.398(3) . ?
C15 C16 1.389(3) . ?
C11 C12 1.371(4) . ?
C20 C19 1.391(3) . ?
C3 C2 1.390(4) . ?
C3 C4 1.376(4) . ?
C23 C24 1.381(4) . ?
C33 C32 1.387(4) . ?
C31 C32 1.378(4) . ?
C5 C4 1.391(4) . ?
C18 C17 1.371(4) . ?
C18 C19 1.389(4) . ?
C26 C25 1.385(4) . ?
C16 C17 1.381(4) . ?
C24 C25 1.375(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C7 124.63(19) . . ?
C28 N5 C29 123.45(18) . . ?
C35 C34 C29 121.1(2) . . ?
C33 C34 C29 119.0(2) . . ?
C33 C34 C35 119.8(2) . . ?
C34 C29 N5 118.5(2) . . ?
C30 C29 N5 123.0(2) . . ?
C30 C29 C34 118.5(2) . . ?
C1 N1 C35 120.93(19) . . ?
C6 C7 N2 114.17(18) . . ?
C15 N3 C14 119.3(2) . . ?
N1 C35 C34 111.24(18) . . ?
C13 C14 N3 124.6(2) . . ?
C13 C8 N2 120.1(2) . . ?
C9 C8 N2 122.1(2) . . ?
C9 C8 C13 117.8(2) . . ?
C27 C22 N4 120.1(2) . . ?
C23 C22 N4 120.8(2) . . ?
C23 C22 C27 119.1(2) . . ?
C21 N4 C22 123.3(2) . . ?
C11 C10 C9 121.7(2) . . ?
C8 C13 C14 123.4(2) . . ?
C12 C13 C14 117.3(2) . . ?
C12 C13 C8 119.3(2) . . ?
C31 C30 C29 120.8(2) . . ?
C10 C9 C8 120.6(2) . . ?
C20 C21 N4 109.44(19) . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 C1 118.8(2) . . ?
C6 C1 N1 119.4(2) . . ?
C2 C1 N1 121.8(2) . . ?
C2 C1 C6 118.7(2) . . ?
C28 C27 C22 121.3(2) . . ?
C26 C27 C22 118.5(2) . . ?
C26 C27 C28 120.2(2) . . ?
C20 C15 N3 117.3(2) . . ?
C16 C15 N3 122.4(2) . . ?
C16 C15 C20 120.2(2) . . ?
C27 C28 N5 113.47(18) . . ?
C12 C11 C10 118.6(2) . . ?
C15 C20 C21 120.5(2) . . ?
C19 C20 C21 120.8(2) . . ?
C19 C20 C15 118.8(2) . . ?
C11 C12 C13 122.0(2) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C2 C1 120.9(2) . . ?
C24 C23 C22 120.2(2) . . ?
C32 C33 C34 121.9(2) . . ?
C32 C31 C30 120.8(2) . . ?
C4 C5 C6 122.3(2) . . ?
C19 C18 C17 120.3(2) . . ?
C25 C26 C27 121.8(3) . . ?
C5 C4 C3 118.6(2) . . ?
C17 C16 C15 120.1(3) . . ?
C16 C17 C18 120.2(3) . . ?
C18 C19 C20 120.4(3) . . ?
C31 C32 C33 119.0(2) . . ?
C25 C24 C23 121.2(3) . . ?
C24 C25 C26 119.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#==END
