# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_PYP
_audit_block_doi                 10.5517/ccdc.csd.cc242l72
_database_code_depnum_ccdc_archive 'CCDC 1968693'
loop_
_audit_author_name
_audit_author_address
Sunjb
;Jilin Unversity
China
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2020-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N5'
_chemical_formula_weight         315.38

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/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                   10.3699(11)
_cell_length_b                   11.8276(13)
_cell_length_c                   12.9546(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.536(4)
_cell_angle_gamma                90
_cell_volume                     1544.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.725
_exptl_crystal_size_mid          0.413
_exptl_crystal_size_min          0.274
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13509
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.852
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             2642
_reflns_number_gt                2175
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0429P)²+0.6612P] 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         2642
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.51434(16) 0.32496(13) 0.55143(13) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.72389(16) 0.40808(14) 0.54799(12) 0.0427(4) Uani 1 1 d . . . . .
N3 N 0.38352(14) 0.39452(12) 0.65949(12) 0.0371(4) Uani 1 1 d . . . . .
N4 N 0.59158(13) 0.53482(11) 0.76090(11) 0.0304(3) Uani 1 1 d . . . . .
N5 N 0.79501(14) 0.57677(13) 0.63071(12) 0.0360(4) Uani 1 1 d . . . . .
C1 C 0.19099(18) 0.53950(16) 0.82103(16) 0.0419(5) Uani 1 1 d . . . . .
H1 H 0.2372 0.6074 0.8332 0.050 Uiso 1 1 calc R U . . .
C2 C 0.07424(19) 0.52755(18) 0.85390(17) 0.0488(5) Uani 1 1 d . . . . .
H2 H 0.0431 0.5867 0.8886 0.059 Uiso 1 1 calc R U . . .
C3 C 0.0039(2) 0.42768(18) 0.83513(18) 0.0502(5) Uani 1 1 d . . . . .
H3 H -0.0737 0.4186 0.8586 0.060 Uiso 1 1 calc R U . . .
C4 C 0.0494(2) 0.34156(17) 0.78138(18) 0.0499(5) Uani 1 1 d . . . . .
H4 H 0.0006 0.2751 0.7664 0.060 Uiso 1 1 calc R U . . .
C5 C 0.16666(19) 0.35317(16) 0.74972(16) 0.0427(5) Uani 1 1 d . . . . .
H5 H 0.1966 0.2940 0.7142 0.051 Uiso 1 1 calc R U . . .
C6 C 0.24077(17) 0.45189(15) 0.77007(14) 0.0341(4) Uani 1 1 d . . . . .
C7 C 0.36904(17) 0.45951(14) 0.73777(14) 0.0326(4) Uani 1 1 d . . . . .
C8 C 0.47403(16) 0.52829(14) 0.79660(13) 0.0312(4) Uani 1 1 d . . . . .
C9 C 0.49900(18) 0.57955(16) 0.89503(14) 0.0391(4) Uani 1 1 d . . . . .
H9 H 0.4385 0.5893 0.9371 0.047 Uiso 1 1 calc R U . . .
C10 C 0.63092(19) 0.61399(17) 0.91994(15) 0.0431(5) Uani 1 1 d . . . . .
H10 H 0.6741 0.6501 0.9822 0.052 Uiso 1 1 calc R U . . .
C11 C 0.68636(18) 0.58591(15) 0.83757(14) 0.0364(4) Uani 1 1 d . . . . .
H11 H 0.7737 0.5993 0.8343 0.044 Uiso 1 1 calc R U . . .
C12 C 0.60157(16) 0.47822(14) 0.66789(13) 0.0306(4) Uani 1 1 d . . . . .
C13 C 0.70735(17) 0.48958(14) 0.61603(13) 0.0322(4) Uani 1 1 d . . . . .
C14 C 0.6279(2) 0.33127(17) 0.52261(16) 0.0465(5) Uani 1 1 d . . . . .
H14 H 0.6432 0.2737 0.4781 0.056 Uiso 1 1 calc R U . . .
C15 C 0.50134(17) 0.40066(14) 0.62706(14) 0.0347(4) Uani 1 1 d . . . . .
C16 C 0.75790(19) 0.69521(15) 0.64583(16) 0.0412(5) Uani 1 1 d . . . . .
H16A H 0.7880 0.7179 0.7195 0.049 Uiso 1 1 calc R U . . .
H16B H 0.6626 0.7055 0.6238 0.049 Uiso 1 1 calc R U . . .
C17 C 0.8280(2) 0.76171(18) 0.57575(18) 0.0522(5) Uani 1 1 d . . . . .
H17A H 0.8479 0.8379 0.6025 0.063 Uiso 1 1 calc R U . . .
H17B H 0.7751 0.7654 0.5034 0.063 Uiso 1 1 calc R U . . .
C18 C 0.9540(2) 0.6941(2) 0.5821(2) 0.0598(6) Uani 1 1 d . . . . .
H18A H 0.9942 0.7122 0.5236 0.072 Uiso 1 1 calc R U . . .
H18B H 1.0180 0.7075 0.6486 0.072 Uiso 1 1 calc R U . . .
C19 C 0.90397(19) 0.57405(18) 0.57483(17) 0.0481(5) Uani 1 1 d . . . . .
H19A H 0.8716 0.5513 0.5014 0.058 Uiso 1 1 calc R U . . .
H19B H 0.9734 0.5223 0.6093 0.058 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 C14 1.319(2) . ?
N1 C15 1.357(2) . ?
N2 C14 1.331(3) . ?
N2 C13 1.344(2) . ?
N3 C7 1.309(2) . ?
N3 C15 1.384(2) . ?
N4 C11 1.364(2) . ?
N4 C12 1.403(2) . ?
N4 C8 1.403(2) . ?
N5 C13 1.358(2) . ?
N5 C16 1.478(2) . ?
N5 C19 1.478(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.391(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.488(2) . ?
C7 C8 1.428(2) . ?
C8 C9 1.381(2) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C15 1.394(2) . ?
C12 C13 1.420(2) . ?
C14 H14 0.9300 . ?
C16 C17 1.510(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.517(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.508(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
C14 N1 C15 114.42(16) . . ?
C14 N2 C13 116.67(16) . . ?
C7 N3 C15 118.29(15) . . ?
C11 N4 C12 130.63(15) . . ?
C11 N4 C8 108.53(14) . . ?
C12 N4 C8 120.07(14) . . ?
C13 N5 C16 123.48(14) . . ?
C13 N5 C19 118.57(15) . . ?
C16 N5 C19 109.77(15) . . ?
C2 C1 C6 121.29(18) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 119.92(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.49(19) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.47(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.99(18) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 117.78(17) . . ?
C5 C6 C7 119.27(16) . . ?
C1 C6 C7 122.95(16) . . ?
N3 C7 C8 122.46(16) . . ?
N3 C7 C6 117.04(15) . . ?
C8 C7 C6 120.30(15) . . ?
C9 C8 N4 106.89(15) . . ?
C9 C8 C7 134.25(16) . . ?
N4 C8 C7 117.90(15) . . ?
C8 C9 C10 107.73(16) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
C11 C10 C9 108.57(17) . . ?
C11 C10 H10 125.7 . . ?
C9 C10 H10 125.7 . . ?
N4 C11 C10 108.25(16) . . ?
N4 C11 H11 125.9 . . ?
C10 C11 H11 125.9 . . ?
C15 C12 N4 116.18(15) . . ?
C15 C12 C13 118.19(15) . . ?
N4 C12 C13 125.55(15) . . ?
N2 C13 N5 116.89(15) . . ?
N2 C13 C12 118.27(16) . . ?
N5 C13 C12 124.84(15) . . ?
N1 C14 N2 129.40(17) . . ?
N1 C14 H14 115.3 . . ?
N2 C14 H14 115.3 . . ?
N1 C15 N3 115.37(16) . . ?
N1 C15 C12 121.12(16) . . ?
N3 C15 C12 123.51(16) . . ?
N5 C16 C17 103.71(15) . . ?
N5 C16 H16A 111.0 . . ?
C17 C16 H16A 111.0 . . ?
N5 C16 H16B 111.0 . . ?
C17 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C16 C17 C18 102.87(17) . . ?
C16 C17 H17A 111.2 . . ?
C18 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C18 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C19 C18 C17 102.32(17) . . ?
C19 C18 H18A 111.3 . . ?
C17 C18 H18A 111.3 . . ?
C19 C18 H18B 111.3 . . ?
C17 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
N5 C19 C18 103.91(17) . . ?
N5 C19 H19A 111.0 . . ?
C18 C19 H19A 111.0 . . ?
N5 C19 H19B 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C2 C3 C4 C5 2.3(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 177.96(17) . . . . ?
C2 C1 C6 C5 2.3(3) . . . . ?
C2 C1 C6 C7 -177.19(17) . . . . ?
C15 N3 C7 C8 -5.8(2) . . . . ?
C15 N3 C7 C6 179.37(15) . . . . ?
C5 C6 C7 N3 24.9(2) . . . . ?
C1 C6 C7 N3 -155.54(18) . . . . ?
C5 C6 C7 C8 -150.03(17) . . . . ?
C1 C6 C7 C8 29.5(3) . . . . ?
C11 N4 C8 C9 1.74(19) . . . . ?
C12 N4 C8 C9 172.72(15) . . . . ?
C11 N4 C8 C7 -168.66(15) . . . . ?
C12 N4 C8 C7 2.3(2) . . . . ?
N3 C7 C8 C9 -160.1(2) . . . . ?
C6 C7 C8 C9 14.6(3) . . . . ?
N3 C7 C8 N4 7.0(2) . . . . ?
C6 C7 C8 N4 -178.29(14) . . . . ?
N4 C8 C9 C10 -1.5(2) . . . . ?
C7 C8 C9 C10 166.58(19) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C12 N4 C11 C10 -170.96(17) . . . . ?
C8 N4 C11 C10 -1.2(2) . . . . ?
C9 C10 C11 N4 0.3(2) . . . . ?
C11 N4 C12 C15 156.89(17) . . . . ?
C8 N4 C12 C15 -11.8(2) . . . . ?
C11 N4 C12 C13 -19.9(3) . . . . ?
C8 N4 C12 C13 171.40(15) . . . . ?
C14 N2 C13 N5 -171.02(16) . . . . ?
C14 N2 C13 C12 9.6(2) . . . . ?
C16 N5 C13 N2 143.04(17) . . . . ?
C19 N5 C13 N2 -2.2(2) . . . . ?
C16 N5 C13 C12 -37.6(3) . . . . ?
C19 N5 C13 C12 177.08(16) . . . . ?
C15 C12 C13 N2 -16.0(2) . . . . ?
N4 C12 C13 N2 160.70(16) . . . . ?
C15 C12 C13 N5 164.68(16) . . . . ?
N4 C12 C13 N5 -18.6(3) . . . . ?
C15 N1 C14 N2 -8.3(3) . . . . ?
C13 N2 C14 N1 2.9(3) . . . . ?
C14 N1 C15 N3 -179.19(16) . . . . ?
C14 N1 C15 C12 0.7(3) . . . . ?
C7 N3 C15 N1 174.99(16) . . . . ?
C7 N3 C15 C12 -4.9(3) . . . . ?
N4 C12 C15 N1 -166.30(15) . . . . ?
C13 C12 C15 N1 10.7(3) . . . . ?
N4 C12 C15 N3 13.6(2) . . . . ?
C13 C12 C15 N3 -169.35(15) . . . . ?
C13 N5 C16 C17 -135.82(17) . . . . ?
C19 N5 C16 C17 12.1(2) . . . . ?
N5 C16 C17 C18 -33.2(2) . . . . ?
C16 C17 C18 C19 42.0(2) . . . . ?
C13 N5 C19 C18 163.74(17) . . . . ?
C16 N5 C19 C18 14.1(2) . . . . ?
C17 C18 C19 N5 -34.3(2) . . . . ?

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
C16 H16B N1 0.97 2.59 3.344(3) 134.8 3_666

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_PIP
_audit_block_doi                 10.5517/ccdc.csd.cc242ld7
_database_code_depnum_ccdc_archive 'CCDC 1968698'
loop_
_audit_author_name
_audit_author_address
Sunjb
;Jilin Unversity
China
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2020-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N5'
_chemical_formula_weight         329.40

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      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                   9.2646(3)
_cell_length_b                   9.2990(3)
_cell_length_c                   10.9654(4)
_cell_angle_alpha                94.2160(10)
_cell_angle_beta                 106.6720(10)
_cell_angle_gamma                108.4760(10)
_cell_volume                     844.15(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.47

_exptl_crystal_description       flake
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.783
_exptl_crystal_size_mid          0.614
_exptl_crystal_size_min          0.115
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26608
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3849
_reflns_number_gt                3125
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0510P)²+0.2574P] 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         3849
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.17514(14) 1.10916(13) 0.48572(12) 0.0392(3) Uani 1 1 d . . . . .
N2 N 0.06423(14) 0.92555(14) 0.28853(11) 0.0403(3) Uani 1 1 d . . . . .
N3 N 0.10842(13) 0.69378(13) 0.27859(11) 0.0360(3) Uani 1 1 d . . . . .
N4 N 0.21831(13) 0.73938(12) 0.54933(10) 0.0322(3) Uani 1 1 d . . . . .
N5 N 0.33730(13) 1.06720(13) 0.67744(11) 0.0351(3) Uani 1 1 d . . . . .
C1 C 0.28879(18) 0.40622(18) 0.29235(15) 0.0447(4) Uani 1 1 d . . . . .
H1 H 0.3687 0.4473 0.3726 0.054 Uiso 1 1 calc R U . . .
C2 C 0.2964(2) 0.2906(2) 0.20981(19) 0.0569(4) Uani 1 1 d . . . . .
H2 H 0.3819 0.2552 0.2342 0.068 Uiso 1 1 calc R U . . .
C3 C 0.1772(2) 0.2280(2) 0.09154(18) 0.0597(5) Uani 1 1 d . . . . .
H3 H 0.1810 0.1486 0.0373 0.072 Uiso 1 1 calc R U . . .
C4 C 0.0526(2) 0.2825(2) 0.05359(16) 0.0570(4) Uani 1 1 d . . . . .
H4 H -0.0266 0.2411 -0.0269 0.068 Uiso 1 1 calc R U . . .
C5 C 0.04488(19) 0.39871(18) 0.13480(14) 0.0449(4) Uani 1 1 d . . . . .
H5 H -0.0394 0.4355 0.1085 0.054 Uiso 1 1 calc R U . . .
C6 C 0.16253(16) 0.46108(15) 0.25586(13) 0.0357(3) Uani 1 1 d . . . . .
C7 C 0.15679(15) 0.59170(15) 0.33789(12) 0.0326(3) Uani 1 1 d . . . . .
C8 C 0.20267(15) 0.60250(15) 0.47508(13) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.22261(18) 0.50047(16) 0.55842(14) 0.0401(3) Uani 1 1 d . . . . .
H9 H 0.2192 0.4007 0.5361 0.048 Uiso 1 1 calc R U . . .
C10 C 0.24875(19) 0.57476(17) 0.68219(14) 0.0435(3) Uani 1 1 d . . . . .
H10 H 0.2654 0.5324 0.7570 0.052 Uiso 1 1 calc R U . . .
C11 C 0.24586(17) 0.72073(16) 0.67541(13) 0.0389(3) Uani 1 1 d . . . . .
H11 H 0.2602 0.7940 0.7445 0.047 Uiso 1 1 calc R U . . .
C12 C 0.19264(15) 0.86019(15) 0.48818(12) 0.0311(3) Uani 1 1 d . . . . .
C13 C 0.23505(15) 1.01386(15) 0.55021(13) 0.0322(3) Uani 1 1 d . . . . .
C14 C 0.08707(17) 1.05602(16) 0.36007(14) 0.0410(3) Uani 1 1 d . . . . .
H14 H 0.0361 1.1191 0.3186 0.049 Uiso 1 1 calc R U . . .
C15 C 0.12062(15) 0.82579(15) 0.35359(13) 0.0329(3) Uani 1 1 d . . . . .
C16 C 0.49733(16) 1.05338(17) 0.70160(14) 0.0404(3) Uani 1 1 d . . . . .
H16A H 0.5607 1.1297 0.6637 0.048 Uiso 1 1 calc R U . . .
H16B H 0.4842 0.9521 0.6601 0.048 Uiso 1 1 calc R U . . .
C17 C 0.5859(2) 1.0765(2) 0.84485(16) 0.0529(4) Uani 1 1 d . . . . .
H17A H 0.6928 1.0732 0.8576 0.064 Uiso 1 1 calc R U . . .
H17B H 0.5287 0.9935 0.8811 0.064 Uiso 1 1 calc R U . . .
C18 C 0.5998(2) 1.2301(2) 0.91462(16) 0.0577(5) Uani 1 1 d . . . . .
H18A H 0.6455 1.2375 1.0073 0.069 Uiso 1 1 calc R U . . .
H18B H 0.6712 1.3136 0.8883 0.069 Uiso 1 1 calc R U . . .
C19 C 0.4352(2) 1.2448(2) 0.88311(17) 0.0595(5) Uani 1 1 d . . . . .
H19A H 0.4470 1.3466 0.9224 0.071 Uiso 1 1 calc R U . . .
H19B H 0.3688 1.1696 0.9199 0.071 Uiso 1 1 calc R U . . .
C20 C 0.35158(19) 1.21976(17) 0.73789(15) 0.0457(4) Uani 1 1 d . . . . .
H20A H 0.2454 1.2262 0.7209 0.055 Uiso 1 1 calc R U . . .
H20B H 0.4132 1.2992 0.7013 0.055 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 C13 1.3312(17) . ?
N1 C14 1.3445(19) . ?
N2 C14 1.3169(19) . ?
N2 C15 1.3539(17) . ?
N3 C7 1.3107(17) . ?
N3 C15 1.3808(17) . ?
N4 C11 1.3665(17) . ?
N4 C12 1.3988(16) . ?
N4 C8 1.4025(16) . ?
N5 C13 1.3899(17) . ?
N5 C20 1.4704(17) . ?
N5 C16 1.4782(17) . ?
C1 C2 1.386(2) . ?
C1 C6 1.389(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3937(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4816(18) . ?
C7 C8 1.4274(18) . ?
C8 C9 1.3825(19) . ?
C9 C10 1.395(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C15 1.3985(18) . ?
C12 C13 1.4167(18) . ?
C14 H14 0.9300 . ?
C16 C17 1.512(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.520(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.517(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.521(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
C13 N1 C14 116.93(12) . . ?
C14 N2 C15 115.41(12) . . ?
C7 N3 C15 117.95(11) . . ?
C11 N4 C12 131.46(12) . . ?
C11 N4 C8 108.58(11) . . ?
C12 N4 C8 119.73(11) . . ?
C13 N5 C20 116.26(11) . . ?
C13 N5 C16 114.56(11) . . ?
C20 N5 C16 111.17(11) . . ?
C2 C1 C6 120.32(15) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.05(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.21(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.11(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.45(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.84(13) . . ?
C1 C6 C7 121.62(12) . . ?
C5 C6 C7 119.38(13) . . ?
N3 C7 C8 122.84(12) . . ?
N3 C7 C6 116.99(12) . . ?
C8 C7 C6 120.17(12) . . ?
C9 C8 N4 107.33(12) . . ?
C9 C8 C7 134.66(13) . . ?
N4 C8 C7 117.66(11) . . ?
C8 C9 C10 107.34(13) . . ?
C8 C9 H9 126.3 . . ?
C10 C9 H9 126.3 . . ?
C11 C10 C9 108.76(13) . . ?
C11 C10 H10 125.6 . . ?
C9 C10 H10 125.6 . . ?
N4 C11 C10 107.98(12) . . ?
N4 C11 H11 126.0 . . ?
C10 C11 H11 126.0 . . ?
C15 C12 N4 116.71(11) . . ?
C15 C12 C13 117.45(12) . . ?
N4 C12 C13 125.83(12) . . ?
N1 C13 N5 119.19(12) . . ?
N1 C13 C12 119.42(12) . . ?
N5 C13 C12 121.39(12) . . ?
N2 C14 N1 127.89(13) . . ?
N2 C14 H14 116.1 . . ?
N1 C14 H14 116.1 . . ?
N2 C15 N3 115.94(12) . . ?
N2 C15 C12 120.96(12) . . ?
N3 C15 C12 123.04(12) . . ?
N5 C16 C17 111.46(12) . . ?
N5 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N5 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 110.88(14) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 110.19(13) . . ?
C19 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 C20 111.81(14) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
N5 C20 C19 109.47(13) . . ?
N5 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
N5 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C1 C6 C7 -175.76(14) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C4 C5 C6 C7 176.44(14) . . . . ?
C15 N3 C7 C8 7.72(19) . . . . ?
C15 N3 C7 C6 -172.29(11) . . . . ?
C1 C6 C7 N3 139.01(14) . . . . ?
C5 C6 C7 N3 -36.22(18) . . . . ?
C1 C6 C7 C8 -40.99(19) . . . . ?
C5 C6 C7 C8 143.77(13) . . . . ?
C11 N4 C8 C9 -0.51(15) . . . . ?
C12 N4 C8 C9 -175.66(11) . . . . ?
C11 N4 C8 C7 173.70(12) . . . . ?
C12 N4 C8 C7 -1.45(17) . . . . ?
N3 C7 C8 C9 162.81(15) . . . . ?
C6 C7 C8 C9 -17.2(2) . . . . ?
N3 C7 C8 N4 -9.41(19) . . . . ?
C6 C7 C8 N4 170.59(11) . . . . ?
N4 C8 C9 C10 0.51(16) . . . . ?
C7 C8 C9 C10 -172.27(15) . . . . ?
C8 C9 C10 C11 -0.33(17) . . . . ?
C12 N4 C11 C10 174.69(13) . . . . ?
C8 N4 C11 C10 0.31(16) . . . . ?
C9 C10 C11 N4 0.01(17) . . . . ?
C11 N4 C12 C15 -161.16(13) . . . . ?
C8 N4 C12 C15 12.70(17) . . . . ?
C11 N4 C12 C13 19.8(2) . . . . ?
C8 N4 C12 C13 -166.37(12) . . . . ?
C14 N1 C13 N5 174.98(12) . . . . ?
C14 N1 C13 C12 -5.39(19) . . . . ?
C20 N5 C13 N1 9.20(18) . . . . ?
C16 N5 C13 N1 -122.74(13) . . . . ?
C20 N5 C13 C12 -170.43(12) . . . . ?
C16 N5 C13 C12 57.63(16) . . . . ?
C15 C12 C13 N1 14.62(18) . . . . ?
N4 C12 C13 N1 -166.30(12) . . . . ?
C15 C12 C13 N5 -165.76(11) . . . . ?
N4 C12 C13 N5 13.3(2) . . . . ?
C15 N2 C14 N1 8.5(2) . . . . ?
C13 N1 C14 N2 -6.9(2) . . . . ?
C14 N2 C15 N3 -175.26(12) . . . . ?
C14 N2 C15 C12 2.10(19) . . . . ?
C7 N3 C15 N2 -177.84(12) . . . . ?
C7 N3 C15 C12 4.86(19) . . . . ?
N4 C12 C15 N2 167.83(11) . . . . ?
C13 C12 C15 N2 -13.01(19) . . . . ?
N4 C12 C15 N3 -15.00(19) . . . . ?
C13 C12 C15 N3 164.16(12) . . . . ?
C13 N5 C16 C17 -166.21(12) . . . . ?
C20 N5 C16 C17 59.46(16) . . . . ?
N5 C16 C17 C18 -55.57(17) . . . . ?
C16 C17 C18 C19 52.65(19) . . . . ?
C17 C18 C19 C20 -54.2(2) . . . . ?
C13 N5 C20 C19 167.14(12) . . . . ?
C16 N5 C20 C19 -59.37(16) . . . . ?
C18 C19 C20 N5 57.41(18) . . . . ?

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
C9 H9 N1 0.93 2.60 3.5253(18) 171.8 1_545
C16 H16B N4 0.97 2.51 3.1653(18) 124.8 .

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.037

