# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ir_35m
_database_code_depnum_ccdc_archive 'CCDC 2001338'
loop_
_audit_author_name
_audit_author_address
'Bhaskar Deka'
;Gauhati University
India
;
_audit_update_record             
;
2020-05-17 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N6'
_chemical_formula_sum            'C20 H18 N6'
_chemical_formula_weight         342.40

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

_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                   5.8660(5)
_cell_length_b                   8.1481(8)
_cell_length_c                   18.3926(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     879.11(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1530
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      26.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   0.985
_exptl_transmission_factor_max   0.989
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3323
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         28.163
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.719
_diffrn_measured_fraction_theta_full 0.654
_diffrn_reflns_Laue_measured_fraction_max 0.719
_diffrn_reflns_Laue_measured_fraction_full 0.654
_diffrn_reflns_point_group_measured_fraction_max 0.719
_diffrn_reflns_point_group_measured_fraction_full 0.654
_reflns_number_total             1548
_reflns_number_gt                937
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0792P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.38(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1548
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 0.1997(4) 0.8769(2) 0.15808(11) 0.0394(5) Uani 1 1 d . . . . .
C2 C 0.0376(5) 0.9515(3) 0.20077(13) 0.0547(7) Uani 1 1 d . . . . .
H2 H -0.103578 0.980129 0.181609 0.066 Uiso 1 1 calc R U . . .
C3 C 0.0892(7) 0.9831(3) 0.27308(15) 0.0682(9) Uani 1 1 d . . . . .
H3 H -0.017004 1.036154 0.302367 0.082 Uiso 1 1 calc R U . . .
N3 N 0.4544(3) 0.98303(19) 0.03062(9) 0.0392(5) Uani 1 1 d . . . . .
C4 C 0.2941(6) 0.9371(4) 0.30160(15) 0.0703(9) Uani 1 1 d . . . . .
H4 H 0.326439 0.957767 0.350247 0.084 Uiso 1 1 calc R U . . .
C5 C 0.4529(5) 0.8602(4) 0.25848(15) 0.0720(9) Uani 1 1 d . . . . .
H5 H 0.591825 0.827672 0.278087 0.086 Uiso 1 1 calc R U . . .
C6 C 0.4061(5) 0.8314(4) 0.18624(13) 0.0565(7) Uani 1 1 d . . . . .
H6 H 0.514292 0.781143 0.156733 0.068 Uiso 1 1 calc R U . . .
C7 C -0.0419(4) 0.7375(3) -0.00477(12) 0.0419(5) Uani 1 1 d . . . . .
C8 C 0.1478(4) 0.8164(3) -0.03472(11) 0.0419(6) Uani 1 1 d . . . . .
H8 H 0.187053 0.822422 -0.083638 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2644(4) 0.8831(2) 0.02294(10) 0.0371(5) Uani 1 1 d . . . . .
C10 C -0.2252(5) 0.6459(3) -0.04234(15) 0.0573(7) Uani 1 1 d . . . . .
H10A H -0.339832 0.614607 -0.007754 0.086 Uiso 1 1 calc R U . . .
H10B H -0.162460 0.549395 -0.064588 0.086 Uiso 1 1 calc R U . . .
H10C H -0.292326 0.714350 -0.079048 0.086 Uiso 1 1 calc R U . . .
N1 N 0.1457(3) 0.8413(2) 0.08415(9) 0.0389(5) Uani 1 1 d . . . . .
N2 N -0.0431(3) 0.7533(2) 0.06784(9) 0.0423(5) 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 C6 1.368(4) . ?
C1 C2 1.374(3) . ?
C1 N1 1.426(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
N3 N3 1.277(3) 3_675 ?
N3 C9 1.388(3) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.342(3) . ?
C7 C8 1.398(3) . ?
C7 C10 1.480(3) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9300 . ?
C9 N1 1.367(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 N2 1.353(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
C6 C1 C2 121.0(2) . . ?
C6 C1 N1 120.1(2) . . ?
C2 C1 N1 118.8(2) . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
N3 N3 C9 111.9(2) 3_675 . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N2 C7 C8 110.6(2) . . ?
N2 C7 C10 120.6(2) . . ?
C8 C7 C10 128.8(2) . . ?
C9 C8 C7 105.90(18) . . ?
C9 C8 H8 127.1 . . ?
C7 C8 H8 127.1 . . ?
N1 C9 C8 106.48(18) . . ?
N1 C9 N3 118.12(19) . . ?
C8 C9 N3 135.28(17) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 N1 C9 111.49(18) . . ?
N2 N1 C1 120.06(16) . . ?
C9 N1 C1 128.44(19) . . ?
C7 N2 N1 105.51(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.4(4) . . . . ?
N1 C1 C2 C3 178.8(2) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
N1 C1 C6 C5 -177.3(2) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
N2 C7 C8 C9 -0.3(2) . . . . ?
C10 C7 C8 C9 179.8(2) . . . . ?
C7 C8 C9 N1 0.8(2) . . . . ?
C7 C8 C9 N3 -175.2(2) . . . . ?
N3 N3 C9 N1 -177.99(19) 3_675 . . . ?
N3 N3 C9 C8 -2.4(3) 3_675 . . . ?
C8 C9 N1 N2 -1.0(2) . . . . ?
N3 C9 N1 N2 175.77(16) . . . . ?
C8 C9 N1 C1 178.1(2) . . . . ?
N3 C9 N1 C1 -5.1(3) . . . . ?
C6 C1 N1 N2 123.5(2) . . . . ?
C2 C1 N1 N2 -53.9(3) . . . . ?
C6 C1 N1 C9 -55.5(3) . . . . ?
C2 C1 N1 C9 127.0(2) . . . . ?
C8 C7 N2 N1 -0.3(2) . . . . ?
C10 C7 N2 N1 179.60(19) . . . . ?
C9 N1 N2 C7 0.8(2) . . . . ?
C1 N1 N2 C7 -178.36(18) . . . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.168



####################################################################### 
# 
# 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_IR141
_database_code_depnum_ccdc_archive 'CCDC 2001339'
loop_
_audit_author_name
_audit_author_address
'Bhaskar Deka'
;Gauhati University
India
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H28 N4'
_chemical_formula_sum            'C27 H28 N4'
_chemical_formula_weight         408.53

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.786(5)
_cell_length_b                   13.940(5)
_cell_length_c                   12.043(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.844(5)
_cell_angle_gamma                90
_cell_volume                     2302.5(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2746
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      22.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69741
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_av_R_equivalents  0.1463
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.241
_diffrn_reflns_theta_max         29.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6117
_reflns_number_gt                2846
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0764P)²+0.0026P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6117
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1788
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.006
_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 0.87585(14) 0.34460(12) 0.57783(15) 0.0425(5) Uani 1 1 d . . . . .
C2 C 0.94644(16) 0.34884(14) 0.66778(18) 0.0550(6) Uani 1 1 d . . . . .
H2 H 0.971050 0.292638 0.701406 0.066 Uiso 1 1 calc R U . . .
C3 C 0.98059(17) 0.43765(15) 0.7079(2) 0.0633(6) Uani 1 1 d . . . . .
H3 H 1.026806 0.440706 0.769685 0.076 Uiso 1 1 calc R U . . .
C4 C 0.94637(18) 0.52044(16) 0.6567(2) 0.0669(7) Uani 1 1 d . . . . .
H4 H 0.969845 0.579529 0.683347 0.080 Uiso 1 1 calc R U . . .
C5 C 0.87768(19) 0.51629(15) 0.5665(2) 0.0699(7) Uani 1 1 d . . . . .
H5 H 0.855376 0.572684 0.531396 0.084 Uiso 1 1 calc R U . . .
C6 C 0.84104(16) 0.42884(14) 0.52692(19) 0.0573(6) Uani 1 1 d . . . . .
H6 H 0.793354 0.426604 0.466524 0.069 Uiso 1 1 calc R U . . .
C7 C 0.75465(15) 0.16558(14) 0.41491(15) 0.0477(5) Uani 1 1 d . . . . .
C8 C 0.76072(14) 0.11529(13) 0.51689(15) 0.0423(5) Uani 1 1 d . . . . .
C9 C 0.81431(13) 0.17396(12) 0.59244(14) 0.0394(5) Uani 1 1 d . . . . .
C10 C 0.70501(19) 0.13480(16) 0.30404(17) 0.0697(7) Uani 1 1 d . . . . .
H10A H 0.706897 0.186318 0.251408 0.105 Uiso 1 1 calc R U . . .
H10B H 0.638415 0.118501 0.311984 0.105 Uiso 1 1 calc R U . . .
H10C H 0.737948 0.079887 0.277769 0.105 Uiso 1 1 calc R U . . .
C11 C 0.71675(15) 0.01985(13) 0.54083(15) 0.0437(5) Uani 1 1 d . . . . .
H11 H 0.667497 0.005583 0.478498 0.052 Uiso 1 1 calc R U . . .
C12 C 0.79115(15) -0.06220(13) 0.54711(16) 0.0468(5) Uani 1 1 d . . . . .
C13 C 0.86222(18) -0.06393(15) 0.47214(19) 0.0642(6) Uani 1 1 d . . . . .
H13 H 0.865245 -0.013813 0.421649 0.077 Uiso 1 1 calc R U . . .
C14 C 0.92782(19) -0.13844(16) 0.4716(2) 0.0750(7) Uani 1 1 d . . . . .
H14 H 0.974452 -0.138345 0.421013 0.090 Uiso 1 1 calc R U . . .
C15 C 0.92436(18) -0.21320(16) 0.5462(2) 0.0697(7) Uani 1 1 d . . . . .
H15 H 0.968227 -0.263859 0.545988 0.084 Uiso 1 1 calc R U . . .
C16 C 0.85535(17) -0.21190(15) 0.62081(19) 0.0615(6) Uani 1 1 d . . . . .
H16 H 0.853128 -0.262404 0.670935 0.074 Uiso 1 1 calc R U . . .
C17 C 0.78855(15) -0.13708(13) 0.62356(17) 0.0505(5) Uani 1 1 d . . . . .
C18 C 0.71547(17) -0.13536(14) 0.70840(18) 0.0605(6) Uani 1 1 d . . . . .
H18A H 0.746701 -0.112184 0.779144 0.073 Uiso 1 1 calc R U . . .
H18B H 0.692216 -0.199956 0.719655 0.073 Uiso 1 1 calc R U . . .
C19 C 0.63025(16) -0.07136(14) 0.67016(19) 0.0555(6) Uani 1 1 d . . . . .
H19A H 0.593802 -0.098898 0.604686 0.067 Uiso 1 1 calc R U . . .
H19B H 0.587020 -0.066453 0.728604 0.067 Uiso 1 1 calc R U . . .
C20 C 0.58362(15) 0.09325(15) 0.62909(16) 0.0529(5) Uani 1 1 d . . . . .
H20A H 0.534977 0.069558 0.571778 0.063 Uiso 1 1 calc R U . . .
H20B H 0.607409 0.154127 0.603780 0.063 Uiso 1 1 calc R U . . .
C21 C 0.53647(15) 0.10919(13) 0.73493(17) 0.0474(5) Uani 1 1 d . . . . .
C22 C 0.43720(17) 0.10241(16) 0.7387(2) 0.0648(6) Uani 1 1 d . . . . .
H22 H 0.397771 0.087617 0.673644 0.078 Uiso 1 1 calc R U . . .
C23 C 0.39440(19) 0.11696(17) 0.8363(2) 0.0754(7) Uani 1 1 d . . . . .
H23 H 0.327187 0.110741 0.835699 0.090 Uiso 1 1 calc R U . . .
C24 C 0.4493(2) 0.14041(17) 0.9340(2) 0.0706(7) Uani 1 1 d . . . . .
C25 C 0.5487(2) 0.14831(18) 0.9310(2) 0.0800(8) Uani 1 1 d . . . . .
H25 H 0.587898 0.164128 0.995873 0.096 Uiso 1 1 calc R U . . .
C26 C 0.59105(17) 0.13310(17) 0.83313(19) 0.0683(7) Uani 1 1 d . . . . .
H26 H 0.658278 0.139206 0.833726 0.082 Uiso 1 1 calc R U . . .
C27 C 0.4014(3) 0.1565(2) 1.0409(2) 0.1178(12) Uani 1 1 d . . . . .
H27A H 0.355283 0.208080 1.029997 0.177 Uiso 1 1 calc R U . . .
H27B H 0.450390 0.172506 1.100399 0.177 Uiso 1 1 calc R U . . .
H27C H 0.368318 0.099025 1.059611 0.177 Uiso 1 1 calc R U . . .
H3A H 0.8460(16) 0.2010(16) 0.7527(18) 0.066(7) Uiso 1 1 d . . . . .
H3B H 0.8096(17) 0.1038(18) 0.7267(19) 0.076(8) Uiso 1 1 d . . . . .
N1 N 0.83739(11) 0.25499(10) 0.53617(12) 0.0433(4) Uani 1 1 d . . . . .
N2 N 0.79999(12) 0.25010(11) 0.42472(13) 0.0494(4) Uani 1 1 d . . . . .
N3 N 0.84491(14) 0.15473(14) 0.70334(14) 0.0492(5) Uani 1 1 d . . . . .
N4 N 0.66549(11) 0.02440(11) 0.64337(12) 0.0449(4) 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 C2 1.382(3) . ?
C1 C6 1.388(3) . ?
C1 N1 1.428(2) . ?
C2 C3 1.393(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.368(3) . ?
C5 C6 1.385(3) . ?
C7 N2 1.333(2) . ?
C7 C8 1.409(3) . ?
C7 C10 1.500(3) . ?
C8 C9 1.380(2) . ?
C8 C11 1.502(3) . ?
C9 N1 1.371(2) . ?
C9 N3 1.385(2) . ?
C11 N4 1.485(2) . ?
C11 C12 1.533(3) . ?
C12 C17 1.395(3) . ?
C12 C13 1.398(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.373(3) . ?
C16 C17 1.394(3) . ?
C17 C18 1.506(3) . ?
C18 C19 1.509(3) . ?
C19 N4 1.468(2) . ?
C20 N4 1.478(2) . ?
C20 C21 1.505(3) . ?
C21 C26 1.376(3) . ?
C21 C22 1.377(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.372(3) . ?
C24 C25 1.379(4) . ?
C24 C27 1.521(3) . ?
C25 C26 1.385(3) . ?
N1 N2 1.390(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
C2 C1 C6 119.64(18) . . ?
C2 C1 N1 121.30(17) . . ?
C6 C1 N1 119.06(18) . . ?
C1 C2 C3 119.73(19) . . ?
C4 C3 C2 120.3(2) . . ?
C5 C4 C3 120.0(2) . . ?
C4 C5 C6 120.6(2) . . ?
C5 C6 C1 119.7(2) . . ?
N2 C7 C8 112.13(17) . . ?
N2 C7 C10 119.93(17) . . ?
C8 C7 C10 127.94(18) . . ?
C9 C8 C7 105.08(16) . . ?
C9 C8 C11 126.69(17) . . ?
C7 C8 C11 128.21(17) . . ?
N1 C9 C8 107.32(16) . . ?
N1 C9 N3 124.94(17) . . ?
C8 C9 N3 127.66(18) . . ?
N4 C11 C8 110.93(14) . . ?
N4 C11 C12 111.31(15) . . ?
C8 C11 C12 112.91(16) . . ?
C17 C12 C13 118.69(19) . . ?
C17 C12 C11 121.93(17) . . ?
C13 C12 C11 119.35(17) . . ?
C14 C13 C12 121.3(2) . . ?
C13 C14 C15 120.0(2) . . ?
C16 C15 C14 119.2(2) . . ?
C15 C16 C17 121.9(2) . . ?
C16 C17 C12 118.86(19) . . ?
C16 C17 C18 121.14(18) . . ?
C12 C17 C18 119.99(18) . . ?
C17 C18 C19 110.85(17) . . ?
N4 C19 C18 109.87(17) . . ?
N4 C20 C21 112.81(16) . . ?
C26 C21 C22 116.5(2) . . ?
C26 C21 C20 121.19(19) . . ?
C22 C21 C20 122.27(19) . . ?
C21 C22 C23 122.0(2) . . ?
C24 C23 C22 121.2(2) . . ?
C23 C24 C25 117.3(2) . . ?
C23 C24 C27 120.8(3) . . ?
C25 C24 C27 121.9(3) . . ?
C24 C25 C26 121.1(2) . . ?
C21 C26 C25 121.8(2) . . ?
C9 N1 N2 110.80(14) . . ?
C9 N1 C1 130.05(15) . . ?
N2 N1 C1 118.05(14) . . ?
C7 N2 N1 104.67(14) . . ?
C19 N4 C20 110.51(16) . . ?
C19 N4 C11 109.88(15) . . ?
C20 N4 C11 110.69(14) . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.049



