# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_20230703al_0m_4_a
_audit_block_doi                 10.5517/ccdc.csd.cc2h2n6g
_database_code_depnum_ccdc_archive 'CCDC 2296455'
loop_
_audit_author_name
_audit_author_address
'Jingyun Ren'
;Northwest University
China
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_audit_creation_date             2023-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3 O3'
_chemical_formula_sum            'C12 H11 N3 O3'
_chemical_formula_weight         245.24
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.753(4)
_cell_length_b                   11.904(6)
_cell_length_c                   12.899(6)
_cell_angle_alpha                87.788(19)
_cell_angle_beta                 81.71(3)
_cell_angle_gamma                86.87(2)
_cell_volume                     1175.6(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2129
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      53.05
_cell_measurement_theta_min      4.35
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_unetI/netI     0.4546
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            4105
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        53.559
_diffrn_reflns_theta_max         53.559
_diffrn_reflns_theta_min         5.022
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1766
_reflns_number_total             4105
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2686
_refine_ls_R_factor_gt           0.1492
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0010P)²+6.6854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2934
_refine_ls_wR_factor_ref         0.3297
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C8) = Uanis(C9)
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C20(H20), C22(H22), C23(H23)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.5547(12) 0.6062(7) 0.3971(6) 0.031(2) Uani 1 1 d . . . . .
C2 C 0.2868(13) 0.6700(8) 0.3371(8) 0.053(3) Uani 1 1 d . . . . .
H2A H 0.3254 0.6358 0.2692 0.079 Uiso 1 1 calc GR . . . .
H2B H 0.2198 0.7406 0.3265 0.079 Uiso 1 1 calc GR . . . .
H2C H 0.2132 0.6182 0.3824 0.079 Uiso 1 1 calc GR . . . .
C3 C 0.7061(12) 0.6421(6) 0.4500(6) 0.033(2) Uani 1 1 d . . . . .
C4 C 0.6416(12) 0.7005(6) 0.5551(7) 0.035(2) Uani 1 1 d . . . . .
H4A H 0.5146 0.6935 0.5761 0.042 Uiso 1 1 calc R . . . .
H4B H 0.7045 0.6687 0.6119 0.042 Uiso 1 1 calc R . . . .
C5 C 0.6858(12) 0.8234(6) 0.5278(7) 0.032(2) Uani 1 1 d . . . . .
C6 C 0.7788(11) 0.8392(6) 0.4281(7) 0.028(2) Uani 1 1 d . . . . .
C7 C 0.8027(11) 0.7333(7) 0.3754(8) 0.035(2) Uani 1 1 d . . . . .
C8 C 0.6425(11) 0.9159(6) 0.5919(7) 0.0347(16) Uani 1 1 d . . . . .
H8 H 0.5785 0.9079 0.6601 0.042 Uiso 1 1 calc R . . . .
C9 C 0.6970(11) 1.0200(6) 0.5516(7) 0.0347(16) Uani 1 1 d . . . . .
H9 H 0.6680 1.0830 0.5948 0.042 Uiso 1 1 calc R . . . .
C10 C 0.7902(11) 1.0388(6) 0.4533(7) 0.030(2) Uani 1 1 d . . . . .
C11 C 0.8305(12) 0.9441(7) 0.3900(7) 0.037(2) Uani 1 1 d . . . . .
H11 H 0.8930 0.9524 0.3214 0.044 Uiso 1 1 calc R . . . .
C12 C 0.8392(13) 1.1549(6) 0.4152(7) 0.045(3) Uani 1 1 d . . . . .
H12A H 0.9635 1.1629 0.4180 0.068 Uiso 1 1 calc GR . . . .
H12B H 0.7700 1.2105 0.4598 0.068 Uiso 1 1 calc GR . . . .
H12C H 0.8160 1.1670 0.3428 0.068 Uiso 1 1 calc GR . . . .
C13 C 0.2278(12) 0.8491(6) 0.9504(7) 0.036(2) Uani 1 1 d . . . . .
C14 C 0.0738(11) 0.8948(7) 0.9000(6) 0.031(2) Uani 1 1 d . . . . .
C15 C -0.1880(12) 0.8544(8) 0.8378(8) 0.049(3) Uani 1 1 d . . . . .
H15A H -0.2844 0.8757 0.8924 0.074 Uiso 1 1 calc GR . . . .
H15B H -0.2220 0.7926 0.7982 0.074 Uiso 1 1 calc GR . . . .
H15C H -0.1607 0.9192 0.7903 0.074 Uiso 1 1 calc GR . . . .
C16 C 0.1700(12) 0.7867(6) 1.0553(7) 0.036(2) Uani 1 1 d . . . . .
H16A H 0.2400 0.8075 1.1094 0.043 Uiso 1 1 calc R . . . .
H16B H 0.0450 0.8042 1.0804 0.043 Uiso 1 1 calc R . . . .
C17 C 0.2017(11) 0.6644(6) 1.0307(7) 0.031(2) Uani 1 1 d . . . . .
C18 C 0.2892(11) 0.6482(6) 0.9330(7) 0.031(2) Uani 1 1 d . . . . .
C19 C 0.3255(11) 0.7551(7) 0.8771(7) 0.030(2) Uani 1 1 d . . . . .
C20 C 0.3340(12) 0.5388(7) 0.8940(7) 0.039(2) Uani 1 1 d . . . . .
H20 H 0.3951 0.5301 0.8252 0.047 Uiso 1 1 calc R . . . .
C21 C 0.2889(12) 0.4456(7) 0.9559(7) 0.034(2) Uani 1 1 d . . . . .
C22 C 0.1932(12) 0.4652(7) 1.0556(7) 0.037(2) Uani 1 1 d . . . . .
H22 H 0.1581 0.4015 1.0986 0.044 Uiso 1 1 calc R . . . .
C23 C 0.1468(12) 0.5706(6) 1.0951(7) 0.035(2) Uani 1 1 d . . . . .
H23 H 0.0808 0.5796 1.1625 0.042 Uiso 1 1 calc R . . . .
C24 C 0.3297(12) 0.3275(6) 0.9189(7) 0.037(2) Uani 1 1 d . . . . .
H24A H 0.4015 0.2863 0.9658 0.056 Uiso 1 1 calc GR . . . .
H24B H 0.3935 0.3299 0.8476 0.056 Uiso 1 1 calc GR . . . .
H24C H 0.2207 0.2894 0.9193 0.056 Uiso 1 1 calc GR . . . .
N1 N 0.8254(10) 0.5472(6) 0.4677(6) 0.040(2) Uani 1 1 d . . . . .
N2 N 0.8891(11) 0.4904(6) 0.3883(7) 0.043(2) Uani 1 1 d . . . . .
N3 N 0.9525(12) 0.4283(6) 0.3300(7) 0.050(2) Uani 1 1 d . . . . .
N4 N 0.3499(10) 0.9359(5) 0.9632(6) 0.039(2) Uani 1 1 d . . . . .
N5 N 0.3984(10) 0.9962(6) 0.8845(6) 0.0363(19) Uani 1 1 d . . . . .
N6 N 0.4551(12) 1.0577(7) 0.8235(7) 0.052(2) Uani 1 1 d . . . . .
O1 O 0.8930(8) 0.7109(4) 0.2906(5) 0.0411(16) Uani 1 1 d . . . . .
O2 O 0.5411(9) 0.5124(5) 0.3678(5) 0.0469(18) Uani 1 1 d . . . . .
O3 O 0.4395(9) 0.6927(5) 0.3867(5) 0.0468(18) Uani 1 1 d . . . . .
O4 O -0.0334(8) 0.8178(4) 0.8866(5) 0.0386(16) Uani 1 1 d . . . . .
O5 O 0.0531(8) 0.9951(5) 0.8725(5) 0.0423(17) Uani 1 1 d . . . . .
O006 O 0.4161(9) 0.7772(5) 0.7942(5) 0.0455(17) 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 C3 1.529(11) . ?
C1 O2 1.207(9) . ?
C1 O3 1.341(10) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 O3 1.467(9) . ?
C3 C4 1.552(11) . ?
C3 C7 1.570(12) . ?
C3 N1 1.454(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.537(11) . ?
C5 C6 1.393(12) . ?
C5 C8 1.400(11) . ?
C6 C7 1.445(12) . ?
C6 C11 1.383(11) . ?
C7 O1 1.241(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(12) . ?
C10 C11 1.412(12) . ?
C10 C12 1.498(11) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.506(12) . ?
C13 C16 1.538(12) . ?
C13 C19 1.583(12) . ?
C13 N4 1.468(10) . ?
C14 O4 1.304(9) . ?
C14 O5 1.241(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 O4 1.470(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.502(11) . ?
C17 C18 1.358(12) . ?
C17 C23 1.412(12) . ?
C18 C19 1.459(12) . ?
C18 C20 1.421(12) . ?
C19 O006 1.219(10) . ?
C20 H20 0.9500 . ?
C20 C21 1.372(12) . ?
C21 C22 1.410(13) . ?
C21 C24 1.505(12) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(11) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 N2 1.273(11) . ?
N2 N3 1.118(10) . ?
N4 N5 1.245(10) . ?
N5 N6 1.114(10) . ?

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
O2 C1 C3 124.4(8) . . ?
O2 C1 O3 124.4(8) . . ?
O3 C1 C3 111.1(7) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C2 H2A 109.5 . . ?
O3 C2 H2B 109.5 . . ?
O3 C2 H2C 109.5 . . ?
C1 C3 C4 112.0(7) . . ?
C1 C3 C7 106.9(6) . . ?
C4 C3 C7 106.2(6) . . ?
N1 C3 C1 111.4(6) . . ?
N1 C3 C4 109.7(7) . . ?
N1 C3 C7 110.5(7) . . ?
C3 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C5 C4 C3 102.1(7) . . ?
C5 C4 H4A 111.3 . . ?
C5 C4 H4B 111.3 . . ?
C6 C5 C4 113.7(7) . . ?
C6 C5 C8 119.4(7) . . ?
C8 C5 C4 126.9(8) . . ?
C5 C6 C7 109.6(7) . . ?
C11 C6 C5 121.9(7) . . ?
C11 C6 C7 128.4(9) . . ?
C6 C7 C3 107.8(8) . . ?
O1 C7 C3 123.2(7) . . ?
O1 C7 C6 128.7(8) . . ?
C5 C8 H8 121.4 . . ?
C9 C8 C5 117.2(9) . . ?
C9 C8 H8 121.4 . . ?
C8 C9 H9 117.5 . . ?
C10 C9 C8 125.0(8) . . ?
C10 C9 H9 117.5 . . ?
C9 C10 C11 116.6(7) . . ?
C9 C10 C12 121.2(8) . . ?
C11 C10 C12 122.2(9) . . ?
C6 C11 C10 119.9(9) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C16 111.7(8) . . ?
C14 C13 C19 107.2(6) . . ?
C16 C13 C19 104.6(6) . . ?
N4 C13 C14 112.7(7) . . ?
N4 C13 C16 111.0(6) . . ?
N4 C13 C19 109.2(7) . . ?
O4 C14 C13 113.0(7) . . ?
O5 C14 C13 123.4(7) . . ?
O5 C14 O4 123.6(8) . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
C13 C16 H16A 110.9 . . ?
C13 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C17 C16 C13 104.3(7) . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
C18 C17 C16 112.7(7) . . ?
C18 C17 C23 119.7(7) . . ?
C23 C17 C16 127.5(8) . . ?
C17 C18 C19 111.4(7) . . ?
C17 C18 C20 122.0(8) . . ?
C20 C18 C19 126.6(9) . . ?
C18 C19 C13 105.7(8) . . ?
O006 C19 C13 122.6(7) . . ?
O006 C19 C18 131.6(8) . . ?
C18 C20 H20 120.1 . . ?
C21 C20 C18 119.8(9) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 116.8(8) . . ?
C20 C21 C24 122.6(9) . . ?
C22 C21 C24 120.6(7) . . ?
C21 C22 H22 117.7 . . ?
C23 C22 C21 124.5(8) . . ?
C23 C22 H22 117.7 . . ?
C17 C23 H23 121.5 . . ?
C22 C23 C17 117.0(9) . . ?
C22 C23 H23 121.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 N1 C3 117.0(7) . . ?
N3 N2 N1 168.9(9) . . ?
N5 N4 C13 116.7(7) . . ?
N6 N5 N4 169.9(8) . . ?
C1 O3 C2 116.9(6) . . ?
C14 O4 C15 117.0(6) . . ?

_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_09_a
_audit_block_doi                 10.5517/ccdc.csd.cc2h2m7g
_database_code_depnum_ccdc_archive 'CCDC 2296425'
loop_
_audit_author_name
_audit_author_address
'Jingyun Ren'
;Northwest University
China
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-21 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         ?
_chemical_formula_sum            'C15 H12 N4 O'
_chemical_formula_weight         264.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.2924(12)
_cell_length_b                   43.711(4)
_cell_length_c                   9.1248(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.601(4)
_cell_angle_gamma                90
_cell_volume                     5242.1(8)
_cell_formula_units_Z            16
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    7791
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      52.82

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             2208
_exptl_transmission_factor_min   0.3078
_exptl_transmission_factor_max   0.7050
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.457
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            20654
_diffrn_reflns_av_unetI/netI     0.1206
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.055
_diffrn_reflns_theta_max         53.199
_diffrn_reflns_theta_full        53.199
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             7549
_reflns_number_gt                5027
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0010P)²+40.7306P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7549
_refine_ls_number_parameters     720
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.1215
_refine_ls_wR_factor_ref         0.3051
_refine_ls_wR_factor_gt          0.2809
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.003
_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 0.1277(10) 0.6830(3) 1.0167(14) 0.045(3) Uani 1 1 d . . . . .
C2 C 0.1967(9) 0.7095(3) 0.9763(16) 0.050(3) Uani 1 1 d . . . . .
C3 C 0.2090(12) 0.7657(3) 1.0116(16) 0.065(4) Uani 1 1 d . . . . .
H3A H 0.160889 0.777358 0.945132 0.098 Uiso 1 1 calc R U . . .
H3B H 0.270300 0.763074 0.969199 0.098 Uiso 1 1 calc R U . . .
H3C H 0.224151 0.776244 1.104466 0.098 Uiso 1 1 calc R U . . .
C4 C 0.0846(8) 0.7301(3) 1.1130(15) 0.041(3) Uani 1 1 d . . . . .
C5 C 0.0617(10) 0.6998(3) 1.1141(15) 0.048(3) Uani 1 1 d . . . . .
C6 C -0.0117(11) 0.6888(3) 1.1930(18) 0.060(4) Uani 1 1 d . . . . .
H6 H -0.025677 0.667999 1.196761 0.071 Uiso 1 1 calc R U . . .
C7 C -0.0653(12) 0.7106(4) 1.2684(17) 0.068(4) Uani 1 1 d . . . . .
H7 H -0.113724 0.704009 1.325302 0.081 Uiso 1 1 calc R U . . .
C8 C -0.0458(11) 0.7403(3) 1.2572(17) 0.059(4) Uani 1 1 d . . . . .
H8 H -0.085013 0.754065 1.302146 0.071 Uiso 1 1 calc R U . . .
C9 C 0.0303(10) 0.7521(3) 1.1816(16) 0.051(3) Uani 1 1 d . . . . .
H9 H 0.043791 0.772984 1.177425 0.061 Uiso 1 1 calc R U . . .
C10 C 0.0706(10) 0.6704(3) 0.8697(16) 0.048(3) Uani 1 1 d . . . . .
C11 C -0.0292(11) 0.6746(3) 0.8298(15) 0.052(3) Uani 1 1 d . . . . .
H11 H -0.067002 0.683924 0.895187 0.062 Uiso 1 1 calc R U . . .
C12 C -0.0774(13) 0.6650(3) 0.6905(17) 0.061(4) Uani 1 1 d . . . . .
H12 H -0.146682 0.668040 0.660460 0.073 Uiso 1 1 calc R U . . .
C13 C -0.0171(14) 0.6508(3) 0.5998(17) 0.063(4) Uani 1 1 d . . . . .
H13 H -0.047851 0.644210 0.506974 0.075 Uiso 1 1 calc R U . . .
C14 C 0.0821(14) 0.6462(3) 0.637(2) 0.068(4) Uani 1 1 d . . . . .
H14 H 0.119604 0.636881 0.571357 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1289(11) 0.6553(3) 0.7763(18) 0.056(4) Uani 1 1 d . . . . .
H15 H 0.197628 0.651414 0.807033 0.068 Uiso 1 1 calc R U . . .
C16 C 0.6345(9) 0.6880(3) 1.0077(15) 0.045(3) Uani 1 1 d . . . . .
C17 C 0.6961(9) 0.7157(3) 0.9675(16) 0.049(3) Uani 1 1 d . . . . .
C18 C 0.7035(12) 0.7714(3) 1.0169(19) 0.071(5) Uani 1 1 d . . . . .
H18A H 0.654126 0.783213 0.953229 0.107 Uiso 1 1 calc R U . . .
H18B H 0.764705 0.769792 0.973410 0.107 Uiso 1 1 calc R U . . .
H18C H 0.718209 0.781192 1.111769 0.107 Uiso 1 1 calc R U . . .
C19 C 0.5824(10) 0.7333(3) 1.1117(16) 0.049(3) Uani 1 1 d . . . . .
C20 C 0.5634(9) 0.7029(3) 1.1028(16) 0.048(3) Uani 1 1 d . . . . .
C21 C 0.4904(10) 0.6900(3) 1.1799(18) 0.057(4) Uani 1 1 d . . . . .
H21 H 0.477948 0.669082 1.177322 0.069 Uiso 1 1 calc R U . . .
C22 C 0.4364(12) 0.7100(4) 1.2617(17) 0.068(4) Uani 1 1 d . . . . .
H22 H 0.388975 0.702076 1.316796 0.081 Uiso 1 1 calc R U . . .
C23 C 0.4533(11) 0.7402(3) 1.2603(17) 0.060(4) Uani 1 1 d . . . . .
H23 H 0.413133 0.752779 1.310086 0.072 Uiso 1 1 calc R U . . .
C24 C 0.5277(11) 0.7541(3) 1.1882(18) 0.060(4) Uani 1 1 d . . . . .
H24 H 0.539910 0.775066 1.190680 0.071 Uiso 1 1 calc R U . . .
C25 C 0.5780(9) 0.6742(3) 0.8606(15) 0.045(3) Uani 1 1 d . . . . .
C26 C 0.4765(11) 0.6760(3) 0.8193(16) 0.050(3) Uani 1 1 d . . . . .
H26 H 0.436678 0.685403 0.882005 0.060 Uiso 1 1 calc R U . . .
C27 C 0.4305(11) 0.6642(3) 0.6851(18) 0.058(4) Uani 1 1 d . . . . .
H27 H 0.360611 0.665545 0.655742 0.070 Uiso 1 1 calc R U . . .
C28 C 0.4948(14) 0.6499(3) 0.5942(19) 0.069(4) Uani 1 1 d . . . . .
H28 H 0.465229 0.641720 0.503924 0.083 Uiso 1 1 calc R U . . .
C29 C 0.5942(14) 0.6478(3) 0.632(2) 0.078(5) Uani 1 1 d . . . . .
H29 H 0.633701 0.638609 0.567894 0.094 Uiso 1 1 calc R U . . .
C30 C 0.6405(11) 0.6598(3) 0.7708(18) 0.056(4) Uani 1 1 d . . . . .
H30 H 0.710269 0.658081 0.801170 0.067 Uiso 1 1 calc R U . . .
C31 C 0.3870(9) 0.5647(3) 0.3803(15) 0.044(3) Uani 1 1 d . . . . .
C32 C 0.3243(12) 0.5371(4) 0.312(2) 0.070(2) Uani 1 1 d . . . . .
C33 C 0.4591(11) 0.5492(3) 0.5032(15) 0.050(3) Uani 1 1 d . . . . .
C34 C 0.4424(10) 0.5180(3) 0.4917(15) 0.047(3) Uani 1 1 d . . . . .
C35 C 0.3267(13) 0.4810(3) 0.339(2) 0.076(5) Uani 1 1 d . . . . .
H35A H 0.380993 0.468781 0.312664 0.113 Uiso 1 1 calc R U . . .
H35B H 0.272281 0.481994 0.257493 0.113 Uiso 1 1 calc R U . . .
H35C H 0.302132 0.472079 0.423408 0.113 Uiso 1 1 calc R U . . .
C36 C 0.5013(13) 0.4976(4) 0.5874(17) 0.064(4) Uani 1 1 d . . . . .
H36 H 0.495600 0.476584 0.573977 0.076 Uiso 1 1 calc R U . . .
C37 C 0.5666(12) 0.5098(4) 0.7000(17) 0.068(5) Uani 1 1 d . . . . .
H37 H 0.602641 0.496740 0.769208 0.081 Uiso 1 1 calc R U . . .
C38 C 0.5819(14) 0.5409(4) 0.7161(18) 0.073(5) Uani 1 1 d . . . . .
H38 H 0.628895 0.548355 0.793722 0.088 Uiso 1 1 calc R U . . .
C39 C 0.5264(12) 0.5616(3) 0.6154(14) 0.059(4) Uani 1 1 d . . . . .
H39 H 0.535364 0.582657 0.625102 0.071 Uiso 1 1 calc R U . . .
C40 C 0.4384(11) 0.5797(3) 0.2593(15) 0.048(3) Uani 1 1 d . . . . .
C41 C 0.5372(11) 0.5758(3) 0.2451(16) 0.053(3) Uani 1 1 d . . . . .
H41 H 0.578243 0.564600 0.317174 0.063 Uiso 1 1 calc R U . . .
C42 C 0.5799(13) 0.5876(3) 0.1297(16) 0.064(4) Uani 1 1 d . . . . .
H42 H 0.649262 0.585454 0.127975 0.077 Uiso 1 1 calc R U . . .
C43 C 0.5201(15) 0.6027(3) 0.0168(16) 0.067(5) Uani 1 1 d . . . . .
H43 H 0.547339 0.609847 -0.064770 0.081 Uiso 1 1 calc R U . . .
C44 C 0.4173(14) 0.6069(3) 0.0273(17) 0.069(4) Uani 1 1 d . . . . .
H44 H 0.376350 0.617760 -0.046532 0.082 Uiso 1 1 calc R U . . .
C45 C 0.3756(14) 0.5954(3) 0.1446(15) 0.063(4) Uani 1 1 d . . . . .
H45 H 0.306537 0.597849 0.148581 0.075 Uiso 1 1 calc R U . . .
C46 C 0.8693(9) 0.4353(3) 0.0672(13) 0.045(3) Uani 1 1 d . . . . .
C47 C 0.8121(9) 0.4647(3) 0.0146(19) 0.056(4) Uani 1 1 d . . . . .
C48 C 0.8216(13) 0.5197(3) 0.075(2) 0.073(5) Uani 1 1 d . . . . .
H48A H 0.781809 0.524938 0.151122 0.109 Uiso 1 1 calc R U . . .
H48B H 0.781159 0.522266 -0.020343 0.109 Uiso 1 1 calc R U . . .
H48C H 0.880180 0.532731 0.082847 0.109 Uiso 1 1 calc R U . . .
C49 C 0.9344(10) 0.4778(3) 0.2052(16) 0.051(3) Uani 1 1 d . . . . .
C50 C 0.9468(10) 0.4468(3) 0.1950(14) 0.044(3) Uani 1 1 d . . . . .
C51 C 1.0193(13) 0.4310(3) 0.2973(14) 0.061(4) Uani 1 1 d . . . . .
H51 H 1.027361 0.409914 0.291210 0.073 Uiso 1 1 calc R U . . .
C52 C 1.0774(13) 0.4479(4) 0.4063(18) 0.066(4) Uani 1 1 d . . . . .
H52 H 1.126221 0.438416 0.474916 0.079 Uiso 1 1 calc R U . . .
C53 C 1.0626(14) 0.4791(4) 0.4129(15) 0.074(5) Uani 1 1 d . . . . .
H53 H 1.100357 0.490066 0.489622 0.089 Uiso 1 1 calc R U . . .
C54 C 0.9949(14) 0.4948(3) 0.3117(15) 0.068(5) Uani 1 1 d . . . . .
H54 H 0.989942 0.516017 0.314642 0.082 Uiso 1 1 calc R U . . .
C55 C 0.9137(10) 0.4211(3) -0.0649(13) 0.042(3) Uani 1 1 d . . . . .
C56 C 0.8515(11) 0.4057(3) -0.1739(15) 0.052(3) Uani 1 1 d . . . . .
H56 H 0.783492 0.402867 -0.164260 0.062 Uiso 1 1 calc R U . . .
C57 C 0.8864(13) 0.3945(3) -0.2951(14) 0.057(4) Uani 1 1 d . . . . .
H57 H 0.842491 0.383842 -0.366091 0.068 Uiso 1 1 calc R U . . .
C58 C 0.9856(12) 0.3988(3) -0.3145(16) 0.056(4) Uani 1 1 d . . . . .
H58 H 1.008998 0.391622 -0.399266 0.067 Uiso 1 1 calc R U . . .
C59 C 1.0502(12) 0.4139(3) -0.2057(19) 0.064(4) Uani 1 1 d . . . . .
H59 H 1.118358 0.416493 -0.215200 0.077 Uiso 1 1 calc R U . . .
C60 C 1.0131(10) 0.4253(3) -0.0817(15) 0.048(3) Uani 1 1 d . . . . .
H60 H 1.056538 0.435826 -0.009594 0.057 Uiso 1 1 calc R U . . .
N1 N 0.1663(8) 0.7361(2) 1.0356(13) 0.050(3) Uani 1 1 d . . . . .
N2 N 0.1923(11) 0.6576(3) 1.0966(15) 0.069(4) Uani 1 1 d . . . . .
N3 N 0.2170(9) 0.6597(2) 1.2312(15) 0.053(3) Uani 1 1 d . . . . .
N4 N 0.2407(12) 0.6585(3) 1.3524(14) 0.080(4) Uani 1 1 d . . . . .
N5 N 0.6640(9) 0.7416(2) 1.0350(13) 0.053(3) Uani 1 1 d . . . . .
N6 N 0.7044(9) 0.6645(2) 1.0847(16) 0.058(3) Uani 1 1 d . . . . .
N7 N 0.7175(9) 0.6642(2) 1.2223(16) 0.053(3) Uani 1 1 d . . . . .
N8 N 0.7335(12) 0.6617(4) 1.3416(14) 0.087(5) Uani 1 1 d . . . . .
N9 N 0.3633(8) 0.5113(2) 0.3763(14) 0.052(3) Uani 1 1 d . . . . .
N10 N 0.3173(11) 0.5882(3) 0.4312(13) 0.071(4) Uani 1 1 d . . . . .
N11 N 0.2962(11) 0.5853(3) 0.5529(18) 0.071(4) Uani 1 1 d . . . . .
N12 N 0.2667(19) 0.5849(5) 0.663(2) 0.145(10) Uani 1 1 d . . . . .
N13 N 0.7930(9) 0.4125(3) 0.1078(13) 0.053(3) Uani 1 1 d . . . . .
N14 N 0.7870(11) 0.4104(3) 0.2401(16) 0.064(3) Uani 1 1 d . . . . .
N15 N 0.7726(16) 0.4069(4) 0.3580(15) 0.111(7) Uani 1 1 d . . . . .
N16 N 0.8536(9) 0.4886(2) 0.0931(14) 0.054(3) Uani 1 1 d . . . . .
O1 O 0.2695(7) 0.7070(2) 0.9097(12) 0.067(3) Uani 1 1 d . . . . .
O2 O 0.7671(7) 0.7150(2) 0.8969(12) 0.066(3) Uani 1 1 d . . . . .
O3 O 0.2518(8) 0.5382(2) 0.2141(14) 0.070(2) Uani 1 1 d . . . . .
O4 O 0.7408(8) 0.4669(2) -0.0863(13) 0.070(3) 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 N2 1.522(17) . ?
C1 C5 1.526(15) . ?
C1 C10 1.540(19) . ?
C1 C2 1.555(17) . ?
C2 O1 1.221(15) . ?
C2 N1 1.370(16) . ?
C3 N1 1.441(16) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.362(16) . ?
C4 C9 1.405(17) . ?
C4 N1 1.405(15) . ?
C5 C6 1.382(18) . ?
C6 C7 1.425(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.33(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.407(19) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.334(19) . ?
C10 C15 1.402(18) . ?
C11 C12 1.40(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.38(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.33(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.38(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N6 1.489(17) . ?
C16 C20 1.522(15) . ?
C16 C17 1.538(16) . ?
C16 C25 1.557(19) . ?
C17 O2 1.219(15) . ?
C17 N5 1.387(16) . ?
C18 N5 1.420(17) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.352(17) . ?
C19 C24 1.412(17) . ?
C19 N5 1.424(16) . ?
C20 C21 1.398(17) . ?
C21 C22 1.411(18) . ?
C21 H21 0.9300 . ?
C22 C23 1.34(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.41(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.347(18) . ?
C25 C30 1.402(17) . ?
C26 C27 1.38(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.42(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.32(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.43(2) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 N10 1.505(15) . ?
C31 C33 1.521(18) . ?
C31 C40 1.531(17) . ?
C31 C32 1.55(2) . ?
C32 O3 1.212(19) . ?
C32 N9 1.339(19) . ?
C33 C39 1.367(19) . ?
C33 C34 1.382(17) . ?
C34 C36 1.40(2) . ?
C34 N9 1.404(18) . ?
C35 N9 1.431(17) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.35(2) . ?
C36 H36 0.9300 . ?
C37 C38 1.38(2) . ?
C37 H37 0.9300 . ?
C38 C39 1.42(2) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 C41 1.349(19) . ?
C40 C45 1.414(19) . ?
C41 C42 1.369(19) . ?
C41 H41 0.9300 . ?
C42 C43 1.37(2) . ?
C42 H42 0.9300 . ?
C43 C44 1.40(2) . ?
C43 H43 0.9300 . ?
C44 C45 1.37(2) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 N13 1.510(15) . ?
C46 C50 1.521(17) . ?
C46 C47 1.530(19) . ?
C46 C55 1.549(15) . ?
C47 O4 1.223(18) . ?
C47 N16 1.338(18) . ?
C48 N16 1.427(17) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.367(17) . ?
C49 C54 1.383(19) . ?
C49 N16 1.447(19) . ?
C50 C51 1.42(2) . ?
C51 C52 1.38(2) . ?
C51 H51 0.9300 . ?
C52 C53 1.38(2) . ?
C52 H52 0.9300 . ?
C53 C54 1.37(2) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 C60 1.365(17) . ?
C55 C56 1.372(18) . ?
C56 C57 1.353(18) . ?
C56 H56 0.9300 . ?
C57 C58 1.37(2) . ?
C57 H57 0.9300 . ?
C58 C59 1.38(2) . ?
C58 H58 0.9300 . ?
C59 C60 1.391(19) . ?
C59 H59 0.9300 . ?
C60 H60 0.9300 . ?
N2 N3 1.226(18) . ?
N3 N4 1.105(16) . ?
N6 N7 1.242(18) . ?
N7 N8 1.083(17) . ?
N10 N11 1.192(18) . ?
N11 N12 1.135(19) . ?
N13 N14 1.225(17) . ?
N14 N15 1.131(18) . ?

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
N2 C1 C5 113.8(10) . . ?
N2 C1 C10 109.0(10) . . ?
C5 C1 C10 115.3(11) . . ?
N2 C1 C2 110.2(11) . . ?
C5 C1 C2 101.1(10) . . ?
C10 C1 C2 106.9(10) . . ?
O1 C2 N1 125.2(12) . . ?
O1 C2 C1 126.1(12) . . ?
N1 C2 C1 108.5(10) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 122.3(11) . . ?
C5 C4 N1 112.0(10) . . ?
C9 C4 N1 125.7(11) . . ?
C4 C5 C6 121.1(11) . . ?
C4 C5 C1 108.3(10) . . ?
C6 C5 C1 130.6(11) . . ?
C5 C6 C7 117.6(12) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C8 C7 C6 119.8(13) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 124.0(13) . . ?
C7 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C4 C9 C8 114.9(12) . . ?
C4 C9 H9 122.5 . . ?
C8 C9 H9 122.5 . . ?
C11 C10 C15 121.1(14) . . ?
C11 C10 C1 122.0(11) . . ?
C15 C10 C1 116.9(12) . . ?
C10 C11 C12 120.6(13) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 116.8(15) . . ?
C13 C12 H12 121.6 . . ?
C11 C12 H12 121.6 . . ?
C14 C13 C12 123.9(15) . . ?
C14 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?
C13 C14 C15 119.0(14) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C10 118.7(14) . . ?
C14 C15 H15 120.7 . . ?
C10 C15 H15 120.7 . . ?
N6 C16 C20 115.0(11) . . ?
N6 C16 C17 109.8(10) . . ?
C20 C16 C17 101.4(9) . . ?
N6 C16 C25 109.1(10) . . ?
C20 C16 C25 113.3(10) . . ?
C17 C16 C25 107.8(10) . . ?
O2 C17 N5 124.8(12) . . ?
O2 C17 C16 125.9(12) . . ?
N5 C17 C16 109.1(10) . . ?
N5 C18 H18A 109.5 . . ?
N5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 123.9(12) . . ?
C20 C19 N5 111.8(11) . . ?
C24 C19 N5 124.3(12) . . ?
C19 C20 C21 120.1(11) . . ?
C19 C20 C16 109.2(10) . . ?
C21 C20 C16 130.6(11) . . ?
C20 C21 C22 117.6(12) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 H21 121.2 . . ?
C23 C22 C21 120.3(13) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 124.1(13) . . ?
C22 C23 H23 118.0 . . ?
C24 C23 H23 118.0 . . ?
C23 C24 C19 113.8(13) . . ?
C23 C24 H24 123.1 . . ?
C19 C24 H24 123.1 . . ?
C26 C25 C30 121.3(14) . . ?
C26 C25 C16 123.5(11) . . ?
C30 C25 C16 115.2(11) . . ?
C25 C26 C27 121.1(13) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C26 C27 C28 117.2(14) . . ?
C26 C27 H27 121.4 . . ?
C28 C27 H27 121.4 . . ?
C29 C28 C27 123.2(17) . . ?
C29 C28 H28 118.4 . . ?
C27 C28 H28 118.4 . . ?
C28 C29 C30 119.1(15) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C25 C30 C29 118.1(14) . . ?
C25 C30 H30 120.9 . . ?
C29 C30 H30 120.9 . . ?
N10 C31 C33 115.2(11) . . ?
N10 C31 C40 106.9(9) . . ?
C33 C31 C40 115.1(10) . . ?
N10 C31 C32 109.8(11) . . ?
C33 C31 C32 101.1(10) . . ?
C40 C31 C32 108.4(12) . . ?
O3 C32 N9 124.8(16) . . ?
O3 C32 C31 125.9(14) . . ?
N9 C32 C31 109.3(13) . . ?
C39 C33 C34 121.8(13) . . ?
C39 C33 C31 130.2(12) . . ?
C34 C33 C31 107.8(12) . . ?
C33 C34 C36 120.8(14) . . ?
C33 C34 N9 111.0(12) . . ?
C36 C34 N9 128.3(13) . . ?
N9 C35 H35A 109.5 . . ?
N9 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N9 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C34 117.3(14) . . ?
C37 C36 H36 121.4 . . ?
C34 C36 H36 121.4 . . ?
C36 C37 C38 122.5(14) . . ?
C36 C37 H37 118.8 . . ?
C38 C37 H37 118.8 . . ?
C37 C38 C39 120.4(16) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C33 C39 C38 116.9(14) . . ?
C33 C39 H39 121.6 . . ?
C38 C39 H39 121.6 . . ?
C41 C40 C45 117.7(13) . . ?
C41 C40 C31 124.1(12) . . ?
C45 C40 C31 117.7(13) . . ?
C40 C41 C42 123.2(14) . . ?
C40 C41 H41 118.4 . . ?
C42 C41 H41 118.4 . . ?
C41 C42 C43 119.9(17) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C42 C43 C44 118.4(14) . . ?
C42 C43 H43 120.8 . . ?
C44 C43 H43 120.8 . . ?
C45 C44 C43 121.2(14) . . ?
C45 C44 H44 119.4 . . ?
C43 C44 H44 119.4 . . ?
C44 C45 C40 119.5(16) . . ?
C44 C45 H45 120.3 . . ?
C40 C45 H45 120.3 . . ?
N13 C46 C50 115.7(10) . . ?
N13 C46 C47 108.1(10) . . ?
C50 C46 C47 102.2(10) . . ?
N13 C46 C55 105.9(9) . . ?
C50 C46 C55 115.9(10) . . ?
C47 C46 C55 108.7(10) . . ?
O4 C47 N16 123.5(13) . . ?
O4 C47 C46 126.6(13) . . ?
N16 C47 C46 109.9(12) . . ?
N16 C48 H48A 109.5 . . ?
N16 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N16 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C50 C49 C54 121.2(14) . . ?
C50 C49 N16 111.0(11) . . ?
C54 C49 N16 127.9(13) . . ?
C49 C50 C51 121.0(12) . . ?
C49 C50 C46 107.7(12) . . ?
C51 C50 C46 131.2(11) . . ?
C52 C51 C50 117.6(13) . . ?
C52 C51 H51 121.2 . . ?
C50 C51 H51 121.2 . . ?
C53 C52 C51 119.6(16) . . ?
C53 C52 H52 120.2 . . ?
C51 C52 H52 120.2 . . ?
C54 C53 C52 123.2(14) . . ?
C54 C53 H53 118.4 . . ?
C52 C53 H53 118.4 . . ?
C53 C54 C49 117.3(14) . . ?
C53 C54 H54 121.4 . . ?
C49 C54 H54 121.4 . . ?
C60 C55 C56 118.1(11) . . ?
C60 C55 C46 121.5(11) . . ?
C56 C55 C46 120.2(12) . . ?
C57 C56 C55 121.9(14) . . ?
C57 C56 H56 119.1 . . ?
C55 C56 H56 119.1 . . ?
C56 C57 C58 120.7(13) . . ?
C56 C57 H57 119.6 . . ?
C58 C57 H57 119.6 . . ?
C57 C58 C59 118.7(13) . . ?
C57 C58 H58 120.7 . . ?
C59 C58 H58 120.7 . . ?
C58 C59 C60 119.9(14) . . ?
C58 C59 H59 120.1 . . ?
C60 C59 H59 120.1 . . ?
C55 C60 C59 120.7(12) . . ?
C55 C60 H60 119.6 . . ?
C59 C60 H60 119.6 . . ?
C2 N1 C4 109.7(10) . . ?
C2 N1 C3 123.7(11) . . ?
C4 N1 C3 126.5(11) . . ?
N3 N2 C1 118.2(11) . . ?
N4 N3 N2 172.9(15) . . ?
C17 N5 C18 123.5(12) . . ?
C17 N5 C19 108.5(10) . . ?
C18 N5 C19 127.9(11) . . ?
N7 N6 C16 117.9(11) . . ?
N8 N7 N6 173.9(15) . . ?
C32 N9 C34 110.5(12) . . ?
C32 N9 C35 125.3(14) . . ?
C34 N9 C35 124.1(13) . . ?
N11 N10 C31 117.1(11) . . ?
N12 N11 N10 171.6(16) . . ?
N14 N13 C46 115.8(11) . . ?
N15 N14 N13 173.0(17) . . ?
C47 N16 C48 126.2(14) . . ?
C47 N16 C49 109.1(11) . . ?
C48 N16 C49 124.7(13) . . ?

_refine_diff_density_max         0.501
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.103



