# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_wmj18081_0m
_audit_block_doi                 10.5517/ccdc.csd.cc21kkry
_database_code_depnum_ccdc_archive 'CCDC 1893720'
loop_
_audit_author_name
_audit_author_address
'zheng ya yun '
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N5 O4'
_chemical_formula_weight         331.33

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           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                   23.832(4)
_cell_length_b                   7.7110(10)
_cell_length_c                   19.479(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.350(12)
_cell_angle_gamma                90
_cell_volume                     3416.8(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3316
_cell_measurement_theta_min      6.763
_cell_measurement_theta_max      106.778

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.513
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4427
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\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            29886
_diffrn_reflns_av_unetI/netI     0.1773
_diffrn_reflns_av_R_equivalents  0.1568
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.381
_diffrn_reflns_theta_max         54.988
_diffrn_reflns_theta_full        53.594
_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             6485
_reflns_number_gt                2598
_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-2013 (Sheldrick, 2013)'
_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)+(0.2000P)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
_refine_ls_extinction_coef       0.0045(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6485
_refine_ls_number_parameters     438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2324
_refine_ls_R_factor_gt           0.1288
_refine_ls_wR_factor_ref         0.4207
_refine_ls_wR_factor_gt          0.3391
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
O1 O 0.86936(17) 0.3306(5) 0.1751(2) 0.0752(12) Uani 1 1 d . . . . .
O2 O 0.9691(3) 0.3465(12) 0.2773(3) 0.175(4) Uani 1 1 d . . . . .
O3 O 1.0190(3) 0.3447(11) 0.2050(3) 0.169(3) Uani 1 1 d . . . . .
N1 N 0.7411(2) 0.6447(6) 0.2628(3) 0.0762(15) Uani 1 1 d . . . . .
H1A H 0.7270 0.7433 0.2702 0.091 Uiso 1 1 calc R U . . .
H1B H 0.7278 0.5506 0.2759 0.091 Uiso 1 1 calc R U . . .
N2 N 0.8614(2) 0.9341(6) 0.1557(3) 0.0807(15) Uani 1 1 d . . . . .
H2A H 0.8454 1.0301 0.1623 0.097 Uiso 1 1 calc R U . . .
H2B H 0.8883 0.9341 0.1344 0.097 Uiso 1 1 calc R U . . .
N3 N 0.80222(18) 0.7897(5) 0.2117(2) 0.0622(12) Uani 1 1 d . . . . .
N4 N 0.80283(18) 0.4785(5) 0.2201(2) 0.0621(12) Uani 1 1 d . . . . .
N5 N 0.9734(3) 0.3509(9) 0.2187(4) 0.105(2) Uani 1 1 d . . . . .
C1 C 0.9186(2) 0.3770(8) 0.1537(3) 0.0738(17) Uani 1 1 d . . . . .
H1 H 0.9211 0.3043 0.1134 0.089 Uiso 1 1 calc R U . . .
C2 C 0.9141(2) 0.5730(8) 0.1315(3) 0.0655(15) Uani 1 1 d . . . . .
H2 H 0.9515 0.6322 0.1540 0.079 Uiso 1 1 calc R U . . .
C3 C 0.8686(2) 0.6279(7) 0.1670(3) 0.0623(14) Uani 1 1 d . . . . .
C4 C 0.8449(2) 0.4861(7) 0.1889(3) 0.0632(14) Uani 1 1 d . . . . .
C5 C 0.7836(2) 0.6378(7) 0.2308(3) 0.0609(14) Uani 1 1 d . . . . .
C6 C 0.8444(2) 0.7838(7) 0.1786(3) 0.0596(14) Uani 1 1 d . . . . .
C7 C 0.8966(3) 0.5931(8) 0.0502(3) 0.0721(16) Uani 1 1 d . . . . .
C8 C 0.9387(3) 0.6254(11) 0.0172(4) 0.106(2) Uani 1 1 d . . . . .
H8 H 0.9777 0.6392 0.0448 0.128 Uiso 1 1 calc R U . . .
C9 C 0.9237(6) 0.6380(15) -0.0574(6) 0.152(5) Uani 1 1 d . . . . .
H9 H 0.9530 0.6599 -0.0790 0.182 Uiso 1 1 calc R U . . .
C10 C 0.8696(7) 0.6195(13) -0.0975(5) 0.139(4) Uani 1 1 d . . . . .
H10 H 0.8606 0.6278 -0.1472 0.166 Uiso 1 1 calc R U . . .
C11 C 0.8254(5) 0.5878(13) -0.0668(5) 0.132(3) Uani 1 1 d . . . . .
H11 H 0.7868 0.5742 -0.0954 0.158 Uiso 1 1 calc R U . . .
C12 C 0.8398(3) 0.5762(11) 0.0085(4) 0.104(2) Uani 1 1 d . . . . .
H12 H 0.8103 0.5570 0.0300 0.124 Uiso 1 1 calc R U . . .
O4 O 0.62932(16) 0.4441(5) 0.3433(2) 0.0705(11) Uani 1 1 d . . . . .
O5 O 0.4789(3) 0.4485(12) 0.3011(4) 0.175(3) Uani 1 1 d . . . . .
O6 O 0.5328(3) 0.4418(10) 0.2320(3) 0.151(3) Uani 1 1 d . . . . .
N6 N 0.6277(2) -0.1594(6) 0.3470(3) 0.0878(17) Uani 1 1 d . . . . .
H6A H 0.6421 -0.2554 0.3373 0.105 Uiso 1 1 calc R U . . .
H6B H 0.6007 -0.1607 0.3680 0.105 Uiso 1 1 calc R U . . .
N7 N 0.7538(2) 0.1330(6) 0.2501(3) 0.0781(15) Uani 1 1 d . . . . .
H7A H 0.7670 0.0350 0.2406 0.094 Uiso 1 1 calc R U . . .
H7B H 0.7683 0.2281 0.2397 0.094 Uiso 1 1 calc R U . . .
N8 N 0.68997(18) -0.0136(6) 0.2962(2) 0.0637(12) Uani 1 1 d . . . . .
N9 N 0.69401(19) 0.2976(6) 0.2961(2) 0.0640(12) Uani 1 1 d . . . . .
N10 N 0.5248(3) 0.4364(8) 0.2917(4) 0.0997(18) Uani 1 1 d . . . . .
C13 C 0.5773(2) 0.4033(8) 0.3600(3) 0.0727(16) Uani 1 1 d . . . . .
H13 H 0.5737 0.4743 0.4002 0.087 Uiso 1 1 calc R U . . .
C14 C 0.5797(2) 0.2051(7) 0.3797(3) 0.0673(15) Uani 1 1 d . . . . .
H14 H 0.5420 0.1493 0.3557 0.081 Uiso 1 1 calc R U . . .
C15 C 0.6253(2) 0.1522(7) 0.3445(3) 0.0604(14) Uani 1 1 d . . . . .
C16 C 0.6515(2) 0.2914(7) 0.3260(3) 0.0586(14) Uani 1 1 d . . . . .
C17 C 0.7106(2) 0.1376(7) 0.2813(3) 0.0608(14) Uani 1 1 d . . . . .
C18 C 0.6472(2) -0.0084(6) 0.3294(3) 0.0619(14) Uani 1 1 d . . . . .
C19 C 0.5956(3) 0.1804(8) 0.4612(3) 0.0726(16) Uani 1 1 d . . . . .
C20 C 0.5523(3) 0.1808(10) 0.4939(4) 0.097(2) Uani 1 1 d . . . . .
H20 H 0.5133 0.1905 0.4659 0.116 Uiso 1 1 calc R U . . .
C21 C 0.5651(5) 0.1672(14) 0.5671(5) 0.132(3) Uani 1 1 d . . . . .
H21 H 0.5351 0.1736 0.5886 0.159 Uiso 1 1 calc R U . . .
C22 C 0.6197(6) 0.1452(12) 0.6067(5) 0.129(3) Uani 1 1 d . . . . .
H22 H 0.6279 0.1325 0.6562 0.155 Uiso 1 1 calc R U . . .
C23 C 0.6657(5) 0.1404(12) 0.5764(5) 0.130(3) Uani 1 1 d . . . . .
H23 H 0.7043 0.1255 0.6052 0.156 Uiso 1 1 calc R U . . .
C24 C 0.6528(3) 0.1583(10) 0.5025(4) 0.102(2) Uani 1 1 d . . . . .
H24 H 0.6828 0.1553 0.4810 0.122 Uiso 1 1 calc R U . . .
O7 O 0.9134(3) 0.0811(9) 1.0346(3) 0.134(2) Uani 1 1 d . . . . .
C25 C 0.8194(5) 0.0843(16) 0.9587(7) 0.174(5) Uani 1 1 d . . . . .
H25A H 0.8039 -0.0199 0.9331 0.261 Uiso 1 1 calc R U . . .
H25B H 0.8023 0.1833 0.9303 0.261 Uiso 1 1 calc R U . . .
H25C H 0.8102 0.0870 1.0034 0.261 Uiso 1 1 calc R U . . .
C26 C 0.8811(5) 0.0877(10) 0.9725(5) 0.115(3) Uani 1 1 d . . . . .
C27 C 0.9077(5) 0.1048(15) 0.9124(5) 0.174(5) Uani 1 1 d . . . . .
H27A H 0.8978 0.2161 0.8899 0.261 Uiso 1 1 calc R U . . .
H27B H 0.8927 0.0150 0.8776 0.261 Uiso 1 1 calc R U . . .
H27C H 0.9496 0.0944 0.9310 0.261 Uiso 1 1 calc R U . . .
O8 O 0.5910(2) 0.6995(8) 0.4810(3) 0.1156(18) Uani 1 1 d . . . . .
C28 C 0.6911(4) 0.6601(16) 0.5336(6) 0.162(4) Uani 1 1 d . . . . .
H28A H 0.7060 0.5443 0.5438 0.243 Uiso 1 1 calc R U . . .
H28B H 0.7150 0.7383 0.5687 0.243 Uiso 1 1 calc R U . . .
H28C H 0.6921 0.6934 0.4865 0.243 Uiso 1 1 calc R U . . .
C29 C 0.6304(4) 0.6667(11) 0.5365(5) 0.106(2) Uani 1 1 d . . . . .
C30 C 0.6173(5) 0.6465(15) 0.6050(5) 0.156(4) Uani 1 1 d . . . . .
H30A H 0.6150 0.7587 0.6253 0.234 Uiso 1 1 calc R U . . .
H30B H 0.6478 0.5800 0.6376 0.234 Uiso 1 1 calc R U . . .
H30C H 0.5804 0.5876 0.5968 0.234 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
O1 C4 1.393(6) . ?
O1 C1 1.405(6) . ?
O2 N5 1.178(7) . ?
O3 N5 1.194(7) . ?
N1 C5 1.340(6) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C6 1.347(6) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C5 1.344(6) . ?
N3 C6 1.347(6) . ?
N4 C4 1.320(6) . ?
N4 C5 1.348(6) . ?
N5 C1 1.535(8) . ?
C1 C2 1.567(8) . ?
C1 H1 0.9800 . ?
C2 C3 1.509(7) . ?
C2 C7 1.521(8) . ?
C2 H2 0.9800 . ?
C3 C4 1.357(7) . ?
C3 C6 1.380(7) . ?
C7 C12 1.362(9) . ?
C7 C8 1.366(9) . ?
C8 C9 1.392(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.302(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.406(11) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
O4 C16 1.373(6) . ?
O4 C13 1.407(6) . ?
O5 N10 1.167(7) . ?
O6 N10 1.233(7) . ?
N6 C18 1.337(6) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 C17 1.342(6) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C17 1.330(6) . ?
N8 C18 1.360(7) . ?
N9 C16 1.311(6) . ?
N9 C17 1.353(6) . ?
N10 C13 1.552(8) . ?
C13 C14 1.573(8) . ?
C13 H13 0.9800 . ?
C14 C15 1.503(7) . ?
C14 C19 1.530(7) . ?
C14 H14 0.9800 . ?
C15 C16 1.344(7) . ?
C15 C18 1.409(7) . ?
C19 C20 1.365(8) . ?
C19 C24 1.372(9) . ?
C20 C21 1.369(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.312(13) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(11) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
O7 C26 1.226(10) . ?
C25 C26 1.413(12) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.494(11) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O8 C29 1.229(9) . ?
C28 C29 1.465(11) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.466(11) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C4 O1 C1 105.8(4) . . ?
C5 N1 H1A 120.0 . . ?
C5 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C5 N3 C6 117.2(4) . . ?
C4 N4 C5 111.8(4) . . ?
O2 N5 O3 124.2(7) . . ?
O2 N5 C1 120.3(6) . . ?
O3 N5 C1 115.3(6) . . ?
O1 C1 N5 107.6(5) . . ?
O1 C1 C2 109.4(4) . . ?
N5 C1 C2 109.0(5) . . ?
O1 C1 H1 110.3 . . ?
N5 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
C3 C2 C7 115.9(5) . . ?
C3 C2 C1 98.3(4) . . ?
C7 C2 C1 111.1(5) . . ?
C3 C2 H2 110.3 . . ?
C7 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
C4 C3 C6 114.6(5) . . ?
C4 C3 C2 109.9(5) . . ?
C6 C3 C2 135.4(5) . . ?
N4 C4 C3 128.7(5) . . ?
N4 C4 O1 118.0(5) . . ?
C3 C4 O1 113.3(5) . . ?
N1 C5 N3 116.9(5) . . ?
N1 C5 N4 116.6(5) . . ?
N3 C5 N4 126.6(5) . . ?
N2 C6 N3 118.0(5) . . ?
N2 C6 C3 120.9(5) . . ?
N3 C6 C3 121.1(5) . . ?
C12 C7 C8 118.5(6) . . ?
C12 C7 C2 121.7(6) . . ?
C8 C7 C2 119.8(6) . . ?
C7 C8 C9 120.5(8) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 121.2(9) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.5(8) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 119.0(9) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C11 120.3(8) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C16 O4 C13 107.2(4) . . ?
C18 N6 H6A 120.0 . . ?
C18 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C17 N7 H7A 120.0 . . ?
C17 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C17 N8 C18 117.1(4) . . ?
C16 N9 C17 112.1(4) . . ?
O5 N10 O6 124.1(7) . . ?
O5 N10 C13 115.6(6) . . ?
O6 N10 C13 120.2(6) . . ?
O4 C13 N10 107.8(5) . . ?
O4 C13 C14 107.6(4) . . ?
N10 C13 C14 109.3(5) . . ?
O4 C13 H13 110.7 . . ?
N10 C13 H13 110.7 . . ?
C14 C13 H13 110.7 . . ?
C15 C14 C19 116.8(5) . . ?
C15 C14 C13 97.5(4) . . ?
C19 C14 C13 110.8(5) . . ?
C15 C14 H14 110.4 . . ?
C19 C14 H14 110.4 . . ?
C13 C14 H14 110.4 . . ?
C16 C15 C18 114.5(5) . . ?
C16 C15 C14 111.3(5) . . ?
C18 C15 C14 134.2(5) . . ?
N9 C16 C15 129.1(5) . . ?
N9 C16 O4 118.9(5) . . ?
C15 C16 O4 112.0(4) . . ?
N8 C17 N7 117.3(5) . . ?
N8 C17 N9 127.0(5) . . ?
N7 C17 N9 115.7(5) . . ?
N6 C18 N8 117.7(5) . . ?
N6 C18 C15 122.2(5) . . ?
N8 C18 C15 120.2(5) . . ?
C20 C19 C24 119.0(6) . . ?
C20 C19 C14 119.8(6) . . ?
C24 C19 C14 121.2(6) . . ?
C19 C20 C21 121.4(8) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 119.6(9) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 121.6(8) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 118.6(9) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C19 C24 C23 119.6(8) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O7 C26 C25 119.9(10) . . ?
O7 C26 C27 119.2(10) . . ?
C25 C26 C27 120.9(10) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C29 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O8 C29 C28 118.6(8) . . ?
O8 C29 C30 120.4(8) . . ?
C28 C29 C30 120.8(9) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
C4 O1 C1 N5 100.8(5) . . . . ?
C4 O1 C1 C2 -17.4(6) . . . . ?
O2 N5 C1 O1 -20.6(9) . . . . ?
O3 N5 C1 O1 162.9(6) . . . . ?
O2 N5 C1 C2 97.9(8) . . . . ?
O3 N5 C1 C2 -78.6(7) . . . . ?
O1 C1 C2 C3 17.4(5) . . . . ?
N5 C1 C2 C3 -100.0(5) . . . . ?
O1 C1 C2 C7 -104.6(5) . . . . ?
N5 C1 C2 C7 138.0(5) . . . . ?
C7 C2 C3 C4 107.2(6) . . . . ?
C1 C2 C3 C4 -11.2(6) . . . . ?
C7 C2 C3 C6 -69.0(8) . . . . ?
C1 C2 C3 C6 172.5(6) . . . . ?
C5 N4 C4 C3 -1.0(8) . . . . ?
C5 N4 C4 O1 179.5(5) . . . . ?
C6 C3 C4 N4 -0.7(9) . . . . ?
C2 C3 C4 N4 -177.9(5) . . . . ?
C6 C3 C4 O1 178.8(5) . . . . ?
C2 C3 C4 O1 1.7(7) . . . . ?
C1 O1 C4 N4 -170.2(5) . . . . ?
C1 O1 C4 C3 10.2(6) . . . . ?
C6 N3 C5 N1 -179.2(5) . . . . ?
C6 N3 C5 N4 -0.1(8) . . . . ?
C4 N4 C5 N1 -179.5(5) . . . . ?
C4 N4 C5 N3 1.5(8) . . . . ?
C5 N3 C6 N2 176.6(5) . . . . ?
C5 N3 C6 C3 -1.9(8) . . . . ?
C4 C3 C6 N2 -176.1(5) . . . . ?
C2 C3 C6 N2 0.0(10) . . . . ?
C4 C3 C6 N3 2.3(8) . . . . ?
C2 C3 C6 N3 178.4(5) . . . . ?
C3 C2 C7 C12 -31.4(9) . . . . ?
C1 C2 C7 C12 79.7(7) . . . . ?
C3 C2 C7 C8 149.9(6) . . . . ?
C1 C2 C7 C8 -99.0(7) . . . . ?
C12 C7 C8 C9 -1.0(11) . . . . ?
C2 C7 C8 C9 177.7(8) . . . . ?
C7 C8 C9 C10 0.1(15) . . . . ?
C8 C9 C10 C11 0.3(17) . . . . ?
C9 C10 C11 C12 0.2(16) . . . . ?
C8 C7 C12 C11 1.6(11) . . . . ?
C2 C7 C12 C11 -177.1(7) . . . . ?
C10 C11 C12 C7 -1.2(13) . . . . ?
C16 O4 C13 N10 -97.0(5) . . . . ?
C16 O4 C13 C14 20.8(6) . . . . ?
O5 N10 C13 O4 -162.5(7) . . . . ?
O6 N10 C13 O4 20.2(8) . . . . ?
O5 N10 C13 C14 80.8(8) . . . . ?
O6 N10 C13 C14 -96.5(7) . . . . ?
O4 C13 C14 C15 -19.6(5) . . . . ?
N10 C13 C14 C15 97.2(5) . . . . ?
O4 C13 C14 C19 102.8(5) . . . . ?
N10 C13 C14 C19 -140.3(5) . . . . ?
C19 C14 C15 C16 -105.5(6) . . . . ?
C13 C14 C15 C16 12.3(6) . . . . ?
C19 C14 C15 C18 71.8(8) . . . . ?
C13 C14 C15 C18 -170.3(6) . . . . ?
C17 N9 C16 C15 2.1(8) . . . . ?
C17 N9 C16 O4 -179.1(4) . . . . ?
C18 C15 C16 N9 0.2(8) . . . . ?
C14 C15 C16 N9 178.1(5) . . . . ?
C18 C15 C16 O4 -178.7(4) . . . . ?
C14 C15 C16 O4 -0.8(6) . . . . ?
C13 O4 C16 N9 168.0(5) . . . . ?
C13 O4 C16 C15 -13.1(6) . . . . ?
C18 N8 C17 N7 178.4(5) . . . . ?
C18 N8 C17 N9 0.5(8) . . . . ?
C16 N9 C17 N8 -2.5(8) . . . . ?
C16 N9 C17 N7 179.6(5) . . . . ?
C17 N8 C18 N6 -177.6(5) . . . . ?
C17 N8 C18 C15 2.1(8) . . . . ?
C16 C15 C18 N6 177.3(5) . . . . ?
C14 C15 C18 N6 0.0(10) . . . . ?
C16 C15 C18 N8 -2.4(8) . . . . ?
C14 C15 C18 N8 -179.7(5) . . . . ?
C15 C14 C19 C20 -162.6(5) . . . . ?
C13 C14 C19 C20 87.0(7) . . . . ?
C15 C14 C19 C24 17.6(9) . . . . ?
C13 C14 C19 C24 -92.7(7) . . . . ?
C24 C19 C20 C21 2.9(11) . . . . ?
C14 C19 C20 C21 -176.9(7) . . . . ?
C19 C20 C21 C22 -3.2(14) . . . . ?
C20 C21 C22 C23 2.0(16) . . . . ?
C21 C22 C23 C24 -0.5(15) . . . . ?
C20 C19 C24 C23 -1.3(11) . . . . ?
C14 C19 C24 C23 178.5(7) . . . . ?
C22 C23 C24 C19 0.1(13) . . . . ?

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
C14 H14 O6 0.98 2.62 3.545(8) 158.3 2_645
C13 H13 O8 0.98 2.30 3.229(8) 158.4 .
N7 H7B N4 0.86 2.18 3.036(6) 175.5 .
N7 H7A N3 0.86 2.21 3.069(6) 177.1 1_545
N6 H6B O8 0.86 2.52 3.183(7) 134.2 1_545
N6 H6A O4 0.86 2.35 3.059(6) 140.6 1_545
C2 H2 O2 0.98 2.57 3.522(8) 164.3 2_755
C1 H1 O7 0.98 2.28 3.231(9) 163.8 1_554
N2 H2B O7 0.86 2.47 3.183(8) 140.2 1_564
N2 H2A O1 0.86 2.38 3.080(6) 138.6 1_565
N1 H1B N9 0.86 2.19 3.046(6) 172.8 .
N1 H1A N8 0.86 2.20 3.053(6) 175.8 1_565

_refine_diff_density_max         0.775
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.109

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dd18202
_database_code_depnum_ccdc_archive 'CCDC 1893721'
loop_
_audit_author_name
_audit_author_address
'zheng ya yun '
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N6 O3'
_chemical_formula_weight         444.49

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'
O O 0.0106 0.0060 '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                   18.8434(7)
_cell_length_b                   9.6451(3)
_cell_length_c                   12.5493(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.3240(10)
_cell_angle_gamma                90
_cell_volume                     2243.87(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4374
_cell_measurement_theta_min      5.360
_cell_measurement_theta_max      54.538

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6672
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            10897
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.680
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4375
_reflns_number_gt                3292
_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-2013 (Sheldrick, 2013)'
_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)+(0.0851P)²+0.8867P] 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
_refine_ls_extinction_coef       0.033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4375
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1739
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O1 O 0.28347(8) 0.91595(16) 0.45957(14) 0.0537(5) Uani 1 1 d . . . . .
O2 O 0.29564(8) 0.66610(17) 0.59765(12) 0.0491(4) Uani 1 1 d . . . . .
N1 N 0.41700(9) 0.67381(19) 0.43471(16) 0.0467(5) Uani 1 1 d . . . . .
N2 N 0.38457(9) 0.80657(18) 0.41600(15) 0.0426(5) Uani 1 1 d . . . . .
N3 N 0.20400(10) 0.6340(2) 0.69331(15) 0.0509(5) Uani 1 1 d . . . . .
N4 N 0.08819(10) 0.5662(2) 0.59189(17) 0.0545(5) Uani 1 1 d . . . . .
N5 N 0.10747(19) 0.5956(3) 0.7761(2) 0.0820(9) Uani 1 1 d . . . . .
N6 N 0.06826(10) 0.5359(3) 0.40745(17) 0.0635(6) Uani 1 1 d . . . . .
H6A H 0.0242 0.5157 0.4103 0.076 Uiso 1 1 calc R U . . .
H6B H 0.0827 0.5357 0.3462 0.076 Uiso 1 1 calc R U . . .
C1 C 0.32109(11) 0.8153(2) 0.45360(18) 0.0401(5) Uani 1 1 d . . . . .
C2 C 0.30535(11) 0.6671(2) 0.48596(17) 0.0401(5) Uani 1 1 d . . . . .
C3 C 0.37436(11) 0.5955(2) 0.47514(19) 0.0444(5) Uani 1 1 d . . . . .
C4 C 0.39501(13) 0.4522(3) 0.5127(3) 0.0669(8) Uani 1 1 d . . . . .
H4A H 0.4432 0.4331 0.5020 0.100 Uiso 1 1 calc R U . . .
H4B H 0.3623 0.3870 0.4721 0.100 Uiso 1 1 calc R U . . .
H4C H 0.3928 0.4440 0.5883 0.100 Uiso 1 1 calc R U . . .
C5 C 0.23262(10) 0.6134(2) 0.41382(17) 0.0372(5) Uani 1 1 d . . . . .
H5 H 0.2130 0.6877 0.3638 0.045 Uiso 1 1 calc R U . . .
C6 C 0.18681(11) 0.6020(2) 0.49959(17) 0.0408(5) Uani 1 1 d . . . . .
C7 C 0.22567(11) 0.6330(2) 0.59947(18) 0.0419(5) Uani 1 1 d . . . . .
C8 C 0.13367(14) 0.5984(3) 0.6827(2) 0.0538(6) Uani 1 1 d . . . . .
C9 C 0.11428(12) 0.5678(2) 0.49812(19) 0.0461(5) Uani 1 1 d . . . . .
C10 C 0.23941(10) 0.4835(2) 0.34811(17) 0.0378(5) Uani 1 1 d . . . . .
C11 C 0.22136(12) 0.3534(2) 0.3814(2) 0.0510(6) Uani 1 1 d . . . . .
H11 H 0.2050 0.3438 0.4466 0.061 Uiso 1 1 calc R U . . .
C12 C 0.22743(14) 0.2372(3) 0.3186(2) 0.0631(7) Uani 1 1 d . . . . .
H12 H 0.2151 0.1504 0.3418 0.076 Uiso 1 1 calc R U . . .
C13 C 0.25154(14) 0.2501(3) 0.2224(2) 0.0638(7) Uani 1 1 d . . . . .
H13 H 0.2557 0.1719 0.1805 0.077 Uiso 1 1 calc R U . . .
C14 C 0.26952(13) 0.3772(3) 0.1878(2) 0.0590(7) Uani 1 1 d . . . . .
H14 H 0.2857 0.3856 0.1223 0.071 Uiso 1 1 calc R U . . .
C15 C 0.26381(12) 0.4943(2) 0.25024(19) 0.0476(5) Uani 1 1 d . . . . .
H15 H 0.2764 0.5806 0.2264 0.057 Uiso 1 1 calc R U . . .
C16 C 0.42666(11) 0.9146(2) 0.38130(17) 0.0419(5) Uani 1 1 d . . . . .
C17 C 0.49869(12) 0.8934(3) 0.3802(2) 0.0530(6) Uani 1 1 d . . . . .
H17 H 0.5198 0.8080 0.4005 0.064 Uiso 1 1 calc R U . . .
C18 C 0.53945(14) 0.9998(3) 0.3488(2) 0.0646(7) Uani 1 1 d . . . . .
H18 H 0.5882 0.9855 0.3485 0.078 Uiso 1 1 calc R U . . .
C19 C 0.50937(15) 1.1256(3) 0.3181(2) 0.0638(7) Uani 1 1 d . . . . .
H19 H 0.5373 1.1967 0.2972 0.077 Uiso 1 1 calc R U . . .
C20 C 0.43771(16) 1.1455(3) 0.3186(2) 0.0684(8) Uani 1 1 d . . . . .
H20 H 0.4169 1.2310 0.2977 0.082 Uiso 1 1 calc R U . . .
C21 C 0.39550(14) 1.0412(3) 0.3495(2) 0.0629(7) Uani 1 1 d . . . . .
H21 H 0.3467 1.0560 0.3489 0.075 Uiso 1 1 calc R U . . .
O3 O 0.04658(16) 0.4596(4) 0.1750(2) 0.1416(14) Uani 1 1 d . . . . .
C22 C 0.07403(15) 0.4367(3) 0.1032(2) 0.0665(8) Uani 1 1 d . . . . .
C23 C 0.0734(3) 0.3052(5) 0.0493(6) 0.194(3) Uani 1 1 d . . . . .
H23A H 0.0600 0.2337 0.0951 0.291 Uiso 1 1 calc R U . . .
H23B H 0.1206 0.2861 0.0341 0.291 Uiso 1 1 calc R U . . .
H23C H 0.0392 0.3080 -0.0173 0.291 Uiso 1 1 calc R U . . .
C24 C 0.1098(2) 0.5520(6) 0.0558(4) 0.137(2) Uani 1 1 d . . . . .
H24A H 0.0763 0.5936 -0.0021 0.206 Uiso 1 1 calc R U . . .
H24B H 0.1506 0.5170 0.0281 0.206 Uiso 1 1 calc R U . . .
H24C H 0.1257 0.6203 0.1105 0.206 Uiso 1 1 calc R U . . .
H5B H 0.1368(19) 0.613(4) 0.833(3) 0.093(12) Uiso 1 1 d . . . . .
H5A H 0.063(2) 0.582(4) 0.776(3) 0.109(14) Uiso 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
O1 C1 1.212(2) . ?
O2 C7 1.361(2) . ?
O2 C2 1.446(3) . ?
N1 C3 1.272(3) . ?
N1 N2 1.420(2) . ?
N2 C1 1.365(3) . ?
N2 C16 1.424(3) . ?
N3 C7 1.314(3) . ?
N3 C8 1.352(3) . ?
N4 C8 1.334(3) . ?
N4 C9 1.354(3) . ?
N5 C8 1.350(3) . ?
N5 H5B 0.84(4) . ?
N5 H5A 0.85(4) . ?
N6 C9 1.337(3) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C1 C2 1.530(3) . ?
C2 C3 1.499(3) . ?
C2 C5 1.588(3) . ?
C3 C4 1.490(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.500(3) . ?
C5 C10 1.518(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.367(3) . ?
C6 C9 1.403(3) . ?
C10 C11 1.384(3) . ?
C10 C15 1.390(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 C21 1.383(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O3 C22 1.138(4) . ?
C22 C23 1.437(5) . ?
C22 C24 1.480(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C7 O2 C2 108.00(16) . . ?
C3 N1 N2 108.48(17) . . ?
C1 N2 N1 112.12(16) . . ?
C1 N2 C16 129.13(18) . . ?
N1 N2 C16 117.61(16) . . ?
C7 N3 C8 111.52(19) . . ?
C8 N4 C9 117.54(19) . . ?
C8 N5 H5B 117(3) . . ?
C8 N5 H5A 121(3) . . ?
H5B N5 H5A 122(4) . . ?
C9 N6 H6A 120.0 . . ?
C9 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O1 C1 N2 129.0(2) . . ?
O1 C1 C2 126.06(19) . . ?
N2 C1 C2 104.91(16) . . ?
O2 C2 C3 110.32(17) . . ?
O2 C2 C1 109.12(17) . . ?
C3 C2 C1 101.15(16) . . ?
O2 C2 C5 107.73(15) . . ?
C3 C2 C5 118.19(18) . . ?
C1 C2 C5 109.99(16) . . ?
N1 C3 C4 121.9(2) . . ?
N1 C3 C2 112.53(19) . . ?
C4 C3 C2 125.4(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 116.42(17) . . ?
C6 C5 C2 99.42(16) . . ?
C10 C5 C2 115.51(16) . . ?
C6 C5 H5 108.3 . . ?
C10 C5 H5 108.3 . . ?
C2 C5 H5 108.3 . . ?
C7 C6 C9 115.1(2) . . ?
C7 C6 C5 111.07(17) . . ?
C9 C6 C5 133.8(2) . . ?
N3 C7 O2 118.11(19) . . ?
N3 C7 C6 128.5(2) . . ?
O2 C7 C6 113.42(19) . . ?
N4 C8 N5 117.2(2) . . ?
N4 C8 N3 127.7(2) . . ?
N5 C8 N3 115.1(2) . . ?
N6 C9 N4 117.1(2) . . ?
N6 C9 C6 123.2(2) . . ?
N4 C9 C6 119.7(2) . . ?
C11 C10 C15 118.2(2) . . ?
C11 C10 C5 122.36(19) . . ?
C15 C10 C5 119.45(18) . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C21 119.8(2) . . ?
C17 C16 N2 120.0(2) . . ?
C21 C16 N2 120.24(19) . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 119.0(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C21 121.3(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 119.3(2) . . ?
C20 C21 H21 120.4 . . ?
C16 C21 H21 120.4 . . ?
O3 C22 C23 125.3(5) . . ?
O3 C22 C24 118.5(4) . . ?
C23 C22 C24 116.1(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
C3 N1 N2 C1 4.7(3) . . . . ?
C3 N1 N2 C16 173.59(19) . . . . ?
N1 N2 C1 O1 172.6(2) . . . . ?
C16 N2 C1 O1 5.3(4) . . . . ?
N1 N2 C1 C2 -8.5(2) . . . . ?
C16 N2 C1 C2 -175.8(2) . . . . ?
C7 O2 C2 C3 -136.31(18) . . . . ?
C7 O2 C2 C1 113.41(18) . . . . ?
C7 O2 C2 C5 -6.0(2) . . . . ?
O1 C1 C2 O2 -56.2(3) . . . . ?
N2 C1 C2 O2 124.83(18) . . . . ?
O1 C1 C2 C3 -172.5(2) . . . . ?
N2 C1 C2 C3 8.5(2) . . . . ?
O1 C1 C2 C5 61.7(3) . . . . ?
N2 C1 C2 C5 -117.20(18) . . . . ?
N2 N1 C3 C4 -174.9(2) . . . . ?
N2 N1 C3 C2 1.6(3) . . . . ?
O2 C2 C3 N1 -121.8(2) . . . . ?
C1 C2 C3 N1 -6.4(2) . . . . ?
C5 C2 C3 N1 113.7(2) . . . . ?
O2 C2 C3 C4 54.6(3) . . . . ?
C1 C2 C3 C4 170.0(2) . . . . ?
C5 C2 C3 C4 -70.0(3) . . . . ?
O2 C2 C5 C6 5.52(19) . . . . ?
C3 C2 C5 C6 131.32(19) . . . . ?
C1 C2 C5 C6 -113.31(18) . . . . ?
O2 C2 C5 C10 -119.86(18) . . . . ?
C3 C2 C5 C10 5.9(3) . . . . ?
C1 C2 C5 C10 121.31(19) . . . . ?
C10 C5 C6 C7 121.4(2) . . . . ?
C2 C5 C6 C7 -3.4(2) . . . . ?
C10 C5 C6 C9 -59.0(3) . . . . ?
C2 C5 C6 C9 176.3(2) . . . . ?
C8 N3 C7 O2 -179.7(2) . . . . ?
C8 N3 C7 C6 0.1(3) . . . . ?
C2 O2 C7 N3 -176.22(18) . . . . ?
C2 O2 C7 C6 4.0(2) . . . . ?
C9 C6 C7 N3 0.4(3) . . . . ?
C5 C6 C7 N3 -179.9(2) . . . . ?
C9 C6 C7 O2 -179.81(19) . . . . ?
C5 C6 C7 O2 -0.1(3) . . . . ?
C9 N4 C8 N5 -179.5(2) . . . . ?
C9 N4 C8 N3 0.4(4) . . . . ?
C7 N3 C8 N4 -0.5(4) . . . . ?
C7 N3 C8 N5 179.4(2) . . . . ?
C8 N4 C9 N6 -179.7(2) . . . . ?
C8 N4 C9 C6 0.2(3) . . . . ?
C7 C6 C9 N6 179.4(2) . . . . ?
C5 C6 C9 N6 -0.3(4) . . . . ?
C7 C6 C9 N4 -0.5(3) . . . . ?
C5 C6 C9 N4 179.8(2) . . . . ?
C6 C5 C10 C11 -16.5(3) . . . . ?
C2 C5 C10 C11 99.6(2) . . . . ?
C6 C5 C10 C15 162.76(18) . . . . ?
C2 C5 C10 C15 -81.2(2) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C5 C10 C11 C12 179.2(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C11 C10 C15 C14 0.2(3) . . . . ?
C5 C10 C15 C14 -179.1(2) . . . . ?
C1 N2 C16 C17 158.5(2) . . . . ?
N1 N2 C16 C17 -8.2(3) . . . . ?
C1 N2 C16 C21 -21.0(4) . . . . ?
N1 N2 C16 C21 172.3(2) . . . . ?
C21 C16 C17 C18 0.9(4) . . . . ?
N2 C16 C17 C18 -178.5(2) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C16 0.5(5) . . . . ?
C17 C16 C21 C20 -1.0(4) . . . . ?
N2 C16 C21 C20 178.5(2) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

