# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p
_audit_block_doi                 10.5517/ccdc.csd.cc2432v6
_database_code_depnum_ccdc_archive 'CCDC 1969177'
loop_
_audit_author_name
_audit_author_address
'Hou-Jin Li'
;Sun Yat sen University
China
;
_audit_update_record             
;
2019-11-30 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Asperdione A'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C14H18N4O2
_chemical_formula_sum            'C14 H19 N4 O2.50'
_chemical_formula_weight         283.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   27.726(2)
_cell_length_b                   14.7975(12)
_cell_length_c                   7.8558(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.294(11)
_cell_angle_gamma                90
_cell_volume                     3223.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'Highly oriented graphite crystal'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.676
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6468
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.644
_diffrn_reflns_theta_max         73.817
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3153
_reflns_number_gt                2189
_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-2013 (Sheldrick, 2013)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0014(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3153
_refine_ls_number_parameters     189
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.1196
_refine_ls_wR_factor_ref         0.3607
_refine_ls_wR_factor_gt          0.3293
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_restrained_S_all      1.251
_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 0.03889(8) 0.09172(14) 0.0465(4) 0.0611(8) Uani 1 1 d . . . . .
O2 O 0.16880(10) -0.16768(16) 0.1743(5) 0.0753(10) Uani 1 1 d . . . . .
N1 N 0.05790(10) -0.05625(17) 0.0542(4) 0.0579(9) Uani 1 1 d . . . . .
H1 H 0.0283 -0.0685 0.0309 0.069 Uiso 1 1 calc R U . . .
N4 N 0.14930(9) -0.02002(17) 0.1649(5) 0.0554(8) Uani 1 1 d . . . . .
H4 H 0.1773 -0.0071 0.2055 0.066 Uiso 1 1 calc R U . . .
N9 N 0.21505(11) 0.1101(2) 0.2497(6) 0.0735(11) Uani 1 1 d . . . . .
N11 N 0.24239(11) 0.2493(2) 0.2719(5) 0.0681(10) Uani 1 1 d . . . . .
H11 H 0.2621 0.2928 0.2929 0.082 Uiso 1 1 calc R U . . .
C2 C 0.06901(10) 0.03103(18) 0.0715(4) 0.0466(8) Uani 1 1 d . . . . .
C3 C 0.11898(10) 0.05247(18) 0.1278(4) 0.0447(8) Uani 1 1 d . . . . .
C5 C 0.13927(12) -0.10786(19) 0.1438(5) 0.0548(9) Uani 1 1 d . . . . .
C6 C 0.09050(11) -0.13317(19) 0.0705(5) 0.0535(9) Uani 1 1 d . . . . .
H6A H 0.0959 -0.1569 -0.0443 0.064 Uiso 1 1 calc R U . . .
C7 C 0.13280(11) 0.13941(19) 0.1394(4) 0.0478(8) Uani 1 1 d . . . . .
H7 H 0.1104 0.1832 0.1081 0.057 Uiso 1 1 calc R U . . .
C8 C 0.17954(11) 0.1706(2) 0.1962(5) 0.0521(8) Uani 1 1 d . . . . .
C10 C 0.25164(15) 0.1614(3) 0.2937(8) 0.0808(15) Uani 1 1 d . . . . .
H10 H 0.2808 0.1391 0.3354 0.097 Uiso 1 1 calc R U . . .
C12 C 0.19628(12) 0.2584(2) 0.2103(5) 0.0531(8) Uani 1 1 d . . . . .
C13 C 0.17240(16) 0.3483(2) 0.1830(6) 0.0684(11) Uani 1 1 d D U . . .
C14 C 0.1447(2) 0.3474(3) 0.0133(8) 0.0886(16) Uani 1 1 d D . . . .
H14 H 0.1592 0.3219 -0.0818 0.106 Uiso 1 1 calc R U . . .
C15 C 0.1008(4) 0.3820(5) -0.0018(17) 0.184(6) Uani 1 1 d D . . . .
H15A H 0.0858 0.4078 0.0922 0.221 Uiso 1 1 calc R U . . .
H15B H 0.0849 0.3805 -0.1063 0.221 Uiso 1 1 calc R U . . .
C16A C 0.1378(3) 0.3590(5) 0.3400(11) 0.0845(15) Uani 0.666(13) 1 d D U P A 1
H16A H 0.1054 0.3438 0.3064 0.127 Uiso 0.666(13) 1 calc R U P A 1
H16B H 0.1387 0.4204 0.3794 0.127 Uiso 0.666(13) 1 calc R U P A 1
H16C H 0.1481 0.3194 0.4298 0.127 Uiso 0.666(13) 1 calc R U P A 1
C16B C 0.1432(5) 0.3920(10) 0.316(2) 0.0845(15) Uani 0.334(13) 1 d D U P A 2
H16D H 0.1165 0.4229 0.2639 0.127 Uiso 0.334(13) 1 calc R U P A 2
H16E H 0.1628 0.4346 0.3772 0.127 Uiso 0.334(13) 1 calc R U P A 2
H16F H 0.1314 0.3470 0.3930 0.127 Uiso 0.334(13) 1 calc R U P A 2
C17A C 0.2064(4) 0.4305(7) 0.190(2) 0.0845(15) Uani 0.543(17) 1 d . U P A 1
H17A H 0.1934 0.4752 0.2652 0.127 Uiso 0.543(17) 1 calc R U P A 1
H17B H 0.2095 0.4557 0.0777 0.127 Uiso 0.543(17) 1 calc R U P A 1
H17C H 0.2376 0.4118 0.2304 0.127 Uiso 0.543(17) 1 calc R U P A 1
C17B C 0.2188(5) 0.4111(8) 0.140(2) 0.0845(15) Uani 0.457(17) 1 d . U P A 2
H17D H 0.2336 0.3904 0.0374 0.127 Uiso 0.457(17) 1 calc R U P A 2
H17E H 0.2417 0.4075 0.2324 0.127 Uiso 0.457(17) 1 calc R U P A 2
H17F H 0.2086 0.4727 0.1263 0.127 Uiso 0.457(17) 1 calc R U P A 2
C18 C 0.06709(14) -0.2067(2) 0.1715(6) 0.0703(12) Uani 1 1 d . . . . .
H18A H 0.0363 -0.2212 0.1218 0.105 Uiso 1 1 calc R U . . .
H18B H 0.0626 -0.1867 0.2866 0.105 Uiso 1 1 calc R U . . .
H18C H 0.0873 -0.2594 0.1710 0.105 Uiso 1 1 calc R U . . .
O1W O 0.0000 0.2356(6) 0.2500 0.178(4) Uani 1 2 d S T P . .
H H 0.0126 0.1892 0.1840 0.266 Uiso 1 1 d 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 C2 1.241(4) . ?
O2 C5 1.229(4) . ?
N1 C2 1.335(4) . ?
N1 C6 1.459(4) . ?
N4 C5 1.339(4) . ?
N4 C3 1.393(4) . ?
N9 C10 1.312(5) . ?
N9 C8 1.394(4) . ?
N11 C10 1.337(5) . ?
N11 C12 1.371(5) . ?
C2 C3 1.486(4) . ?
C3 C7 1.345(4) . ?
C5 C6 1.514(4) . ?
C6 C18 1.497(5) . ?
C7 C8 1.444(4) . ?
C8 C12 1.385(4) . ?
C12 C13 1.500(5) . ?
C13 C16B 1.473(9) . ?
C13 C14 1.535(6) . ?
C13 C17A 1.540(9) . ?
C13 C16A 1.574(7) . ?
C13 C17B 1.625(14) . ?
C14 C15 1.328(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
C2 N1 C6 127.1(3) . . ?
C5 N4 C3 126.6(3) . . ?
C10 N9 C8 104.6(3) . . ?
C10 N11 C12 108.6(3) . . ?
O1 C2 N1 122.0(3) . . ?
O1 C2 C3 121.2(2) . . ?
N1 C2 C3 116.8(3) . . ?
C7 C3 N4 123.4(3) . . ?
C7 C3 C2 119.3(3) . . ?
N4 C3 C2 117.3(2) . . ?
O2 C5 N4 122.5(3) . . ?
O2 C5 C6 119.3(3) . . ?
N4 C5 C6 118.1(3) . . ?
N1 C6 C18 110.1(3) . . ?
N1 C6 C5 113.1(2) . . ?
C18 C6 C5 111.5(3) . . ?
C3 C7 C8 125.5(3) . . ?
C12 C8 N9 110.1(3) . . ?
C12 C8 C7 128.6(3) . . ?
N9 C8 C7 121.3(3) . . ?
N9 C10 N11 112.4(3) . . ?
N11 C12 C8 104.3(3) . . ?
N11 C12 C13 123.2(3) . . ?
C8 C12 C13 132.3(3) . . ?
C16B C13 C12 122.1(7) . . ?
C16B C13 C14 110.2(8) . . ?
C12 C13 C14 109.5(3) . . ?
C12 C13 C17A 115.2(5) . . ?
C14 C13 C17A 109.9(6) . . ?
C12 C13 C16A 104.3(4) . . ?
C14 C13 C16A 112.2(5) . . ?
C17A C13 C16A 105.7(7) . . ?
C16B C13 C17B 109.5(9) . . ?
C12 C13 C17B 100.8(6) . . ?
C14 C13 C17B 102.6(7) . . ?
C15 C14 C13 121.9(7) . . ?

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
N1 H1 O1 0.86 1.99 2.843(3) 174.1 5
N4 H4 N9 0.86 2.05 2.732(4) 135.2 .
N11 H11 O2 0.86 2.02 2.782(4) 147.4 4
C18 H18B O1 0.96 2.57 3.494(6) 162.4 6_556
O1W H O1 0.93 1.95 2.876(7) 179.8 .

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.117

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_compound_source        'Marine Fungus Aspergillus sp. XBB-4'
