# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

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

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2004249'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2020-05-16 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2020-05-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
miquel.barcelo@uib.es
jfa950@uib.es
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N5 O2'
_chemical_formula_sum            'C10 H13 N5 O2'
_chemical_formula_weight         235.25
_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 0.0181 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.9276(12)
_cell_length_b                   4.6593(4)
_cell_length_c                   24.5504(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.376(3)
_cell_angle_gamma                90
_cell_volume                     2136.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.048
_cell_measurement_theta_min      2.740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1485 before and 0.0492 after correction.
The Ratio of minimum to maximum transmission is 0.8051.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15161
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.569
_diffrn_reflns_theta_max         66.569
_diffrn_reflns_theta_min         2.742
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3472
_reflns_number_total             3774
_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       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.058
_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)+(0.0370P)²+0.8954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0850
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C10'(H10C,
 H10D), C11'(H11C,H11D), C12'(H12C,H12D), C13'(H13C,H13D)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), N9(H9), N6(H6), C2'(H2'), C8'(H8'), N9'(H9'), N6'(H6')
2.c Idealised tetrahedral OH refined as rotating group:
 O15(H15), O15'(H15')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.39316(5) -0.9528(2) -0.04613(4) 0.0212(2) Uani 1 1 d . . . . .
C2 C 0.42134(7) -0.7566(3) -0.00914(5) 0.0227(3) Uani 1 1 d . . . . .
H2 H 0.463328 -0.664706 -0.017017 0.027 Uiso 1 1 calc R U . . .
N3 N 0.39946(5) -0.6706(2) 0.03705(4) 0.0208(2) Uani 1 1 d . . . . .
C4 C 0.33982(6) -0.8162(3) 0.04471(5) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.30486(6) -1.0244(3) 0.01069(5) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.33300(6) -1.0911(3) -0.03773(5) 0.0183(3) Uani 1 1 d . . . . .
N7 N 0.24592(5) -1.1260(2) 0.03183(4) 0.0203(2) Uani 1 1 d . . . . .
C8 C 0.24740(7) -0.9771(3) 0.07757(5) 0.0213(3) Uani 1 1 d . . . . .
H8 H 0.213038 -1.000433 0.101446 0.026 Uiso 1 1 calc R U . . .
N9 N 0.30198(5) -0.7885(2) 0.08752(4) 0.0199(2) Uani 1 1 d . . . . .
H9 H 0.311445 -0.671086 0.115846 0.024 Uiso 1 1 calc R U . . .
N6 N 0.30221(5) -1.2815(2) -0.07436(4) 0.0197(2) Uani 1 1 d . . . . .
H6 H 0.265425 -1.379067 -0.066360 0.024 Uiso 1 1 calc R U . . .
C10 C 0.32562(6) -1.3386(3) -0.12691(5) 0.0208(3) Uani 1 1 d . . . . .
H10A H 0.365265 -1.479634 -0.121644 0.025 Uiso 1 1 calc R U . . .
H10B H 0.343317 -1.159290 -0.141626 0.025 Uiso 1 1 calc R U . . .
C11 C 0.26306(6) -1.4563(3) -0.16746(5) 0.0193(3) Uani 1 1 d . . . . .
H11A H 0.243528 -1.627034 -0.151074 0.023 Uiso 1 1 calc R U . . .
H11B H 0.280516 -1.518344 -0.201475 0.023 Uiso 1 1 calc R U . . .
C12 C 0.20344(6) -1.2375(3) -0.18257(5) 0.0192(3) Uani 1 1 d . . . . .
H12A H 0.221956 -1.073517 -0.201674 0.023 Uiso 1 1 calc R U . . .
H12B H 0.188601 -1.163898 -0.148330 0.023 Uiso 1 1 calc R U . . .
C13 C 0.13802(6) -1.3636(3) -0.21987(5) 0.0201(3) Uani 1 1 d . . . . .
H13A H 0.152300 -1.437955 -0.254258 0.024 Uiso 1 1 calc R U . . .
H13B H 0.118438 -1.525245 -0.200802 0.024 Uiso 1 1 calc R U . . .
C14 C 0.08181(6) -1.1359(3) -0.23361(5) 0.0196(3) Uani 1 1 d . . . . .
O15 O 0.08216(5) -1.0121(2) -0.28190(3) 0.0216(2) Uani 1 1 d . . . . .
H15 H 0.050126 -0.885735 -0.287080 0.032 Uiso 1 1 calc R U . . .
O14 O 0.04191(5) -1.0648(2) -0.20187(4) 0.0273(2) Uani 1 1 d . . . . .
N1' N 0.34175(5) -0.1697(2) 0.25889(4) 0.0203(2) Uani 1 1 d . . . . .
C2' C 0.31814(6) -0.3572(3) 0.21912(5) 0.0205(3) Uani 1 1 d . . . . .
H2' H 0.277095 -0.464772 0.224243 0.025 Uiso 1 1 calc R U . . .
N3' N 0.34441(5) -0.4141(2) 0.17305(4) 0.0201(2) Uani 1 1 d . . . . .
C4' C 0.40185(6) -0.2496(3) 0.16893(5) 0.0172(3) Uani 1 1 d . . . . .
C5' C 0.43162(6) -0.0443(3) 0.20596(5) 0.0176(3) Uani 1 1 d . . . . .
C6' C 0.40003(6) -0.0088(3) 0.25414(5) 0.0181(3) Uani 1 1 d . . . . .
N7' N 0.48893(5) 0.0870(2) 0.18720(4) 0.0183(2) Uani 1 1 d . . . . .
C8' C 0.49259(6) -0.0429(3) 0.13994(5) 0.0184(3) Uani 1 1 d . . . . .
H8' H 0.527332 0.002440 0.117378 0.022 Uiso 1 1 calc R U . . .
N9' N 0.44178(5) -0.2474(2) 0.12690(4) 0.0181(2) Uani 1 1 d . . . . .
H9' H 0.435551 -0.357202 0.097341 0.022 Uiso 1 1 calc R U . . .
N6' N 0.42525(5) 0.1742(2) 0.29415(4) 0.0199(2) Uani 1 1 d . . . . .
H6' H 0.463417 0.276044 0.290672 0.024 Uiso 1 1 calc R U . . .
C10' C 0.39274(6) 0.2144(3) 0.34348(5) 0.0217(3) Uani 1 1 d . . . . .
H10C H 0.378513 0.025933 0.356858 0.026 Uiso 1 1 calc R U . . .
H10D H 0.349171 0.334029 0.334497 0.026 Uiso 1 1 calc R U . . .
C11' C 0.44554(6) 0.3595(3) 0.38835(5) 0.0206(3) Uani 1 1 d . . . . .
H11C H 0.420674 0.409910 0.419535 0.025 Uiso 1 1 calc R U . . .
H11D H 0.462533 0.539973 0.373565 0.025 Uiso 1 1 calc R U . . .
C12' C 0.50990(6) 0.1707(3) 0.40959(5) 0.0213(3) Uani 1 1 d . . . . .
H12C H 0.529916 0.093746 0.377742 0.026 Uiso 1 1 calc R U . . .
H12D H 0.493838 0.005936 0.429920 0.026 Uiso 1 1 calc R U . . .
C13' C 0.56876(7) 0.3322(3) 0.44766(5) 0.0248(3) Uani 1 1 d . . . . .
H13C H 0.581846 0.508044 0.428987 0.030 Uiso 1 1 calc R U . . .
H13D H 0.550957 0.390021 0.481785 0.030 Uiso 1 1 calc R U . . .
C14' C 0.63335(7) 0.1445(3) 0.46207(5) 0.0231(3) Uani 1 1 d . . . . .
O15' O 0.63712(5) 0.0058(2) 0.50913(4) 0.0265(2) Uani 1 1 d . . . . .
H15' H 0.673571 -0.099780 0.513798 0.040 Uiso 1 1 calc R U . . .
O14' O 0.67743(5) 0.1166(3) 0.43153(4) 0.0356(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
N1 C2 1.3366(17) . ?
N1 C6 1.3532(16) . ?
C2 H2 0.9500 . ?
C2 N3 1.3307(17) . ?
N3 C4 1.3560(16) . ?
C4 C5 1.3770(18) . ?
C4 N9 1.3709(16) . ?
C5 C6 1.4143(17) . ?
C5 N7 1.3879(16) . ?
C6 N6 1.3284(16) . ?
N7 C8 1.3164(17) . ?
C8 H8 0.9500 . ?
C8 N9 1.3479(17) . ?
N9 H9 0.8800 . ?
N6 H6 0.8800 . ?
N6 C10 1.4553(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5197(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5210(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5322(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5015(18) . ?
C14 O15 1.3194(15) . ?
C14 O14 1.2160(16) . ?
O15 H15 0.8400 . ?
N1' C2' 1.3316(17) . ?
N1' C6' 1.3545(16) . ?
C2' H2' 0.9500 . ?
C2' N3' 1.3343(16) . ?
N3' C4' 1.3475(16) . ?
C4' C5' 1.3755(18) . ?
C4' N9' 1.3747(15) . ?
C5' C6' 1.4193(17) . ?
C5' N7' 1.3878(16) . ?
C6' N6' 1.3292(17) . ?
N7' C8' 1.3203(16) . ?
C8' H8' 0.9500 . ?
C8' N9' 1.3546(16) . ?
N9' H9' 0.8800 . ?
N6' H6' 0.8800 . ?
N6' C10' 1.4572(15) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C10' C11' 1.5203(17) . ?
C11' H11C 0.9900 . ?
C11' H11D 0.9900 . ?
C11' C12' 1.5241(17) . ?
C12' H12C 0.9900 . ?
C12' H12D 0.9900 . ?
C12' C13' 1.5301(18) . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C13' C14' 1.4977(18) . ?
C14' O15' 1.3156(17) . ?
C14' O14' 1.2161(16) . ?
O15' H15' 0.8400 . ?

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 118.34(11) . . ?
N1 C2 H2 115.1 . . ?
N3 C2 N1 129.77(12) . . ?
N3 C2 H2 115.1 . . ?
C2 N3 C4 110.45(11) . . ?
N3 C4 C5 126.64(11) . . ?
N3 C4 N9 127.59(11) . . ?
N9 C4 C5 105.77(10) . . ?
C4 C5 C6 117.07(11) . . ?
C4 C5 N7 110.46(11) . . ?
N7 C5 C6 132.45(11) . . ?
N1 C6 C5 117.70(11) . . ?
N6 C6 N1 120.15(11) . . ?
N6 C6 C5 122.15(11) . . ?
C8 N7 C5 103.45(10) . . ?
N7 C8 H8 123.0 . . ?
N7 C8 N9 114.03(11) . . ?
N9 C8 H8 123.0 . . ?
C4 N9 H9 126.9 . . ?
C8 N9 C4 106.29(10) . . ?
C8 N9 H9 126.9 . . ?
C6 N6 H6 118.0 . . ?
C6 N6 C10 123.97(10) . . ?
C10 N6 H6 118.0 . . ?
N6 C10 H10A 109.8 . . ?
N6 C10 H10B 109.8 . . ?
N6 C10 C11 109.23(10) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C12 112.70(10) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C11 C12 C13 112.58(10) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 C12 109.71(10) . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
O15 C14 C13 113.80(10) . . ?
O14 C14 C13 122.68(11) . . ?
O14 C14 O15 123.45(12) . . ?
C14 O15 H15 109.5 . . ?
C2' N1' C6' 118.73(11) . . ?
N1' C2' H2' 115.7 . . ?
N1' C2' N3' 128.68(12) . . ?
N3' C2' H2' 115.7 . . ?
C2' N3' C4' 111.54(11) . . ?
N3' C4' C5' 126.48(11) . . ?
N3' C4' N9' 127.56(11) . . ?
N9' C4' C5' 105.95(11) . . ?
C4' C5' C6' 116.68(11) . . ?
C4' C5' N7' 110.20(11) . . ?
N7' C5' C6' 133.11(11) . . ?
N1' C6' C5' 117.82(11) . . ?
N6' C6' N1' 119.41(11) . . ?
N6' C6' C5' 122.77(11) . . ?
C8' N7' C5' 104.20(10) . . ?
N7' C8' H8' 123.4 . . ?
N7' C8' N9' 113.16(10) . . ?
N9' C8' H8' 123.4 . . ?
C4' N9' H9' 126.8 . . ?
C8' N9' C4' 106.49(10) . . ?
C8' N9' H9' 126.8 . . ?
C6' N6' H6' 118.4 . . ?
C6' N6' C10' 123.17(10) . . ?
C10' N6' H6' 118.4 . . ?
N6' C10' H10C 109.7 . . ?
N6' C10' H10D 109.7 . . ?
N6' C10' C11' 110.04(10) . . ?
H10C C10' H10D 108.2 . . ?
C11' C10' H10C 109.7 . . ?
C11' C10' H10D 109.7 . . ?
C10' C11' H11C 109.1 . . ?
C10' C11' H11D 109.1 . . ?
C10' C11' C12' 112.68(11) . . ?
H11C C11' H11D 107.8 . . ?
C12' C11' H11C 109.1 . . ?
C12' C11' H11D 109.1 . . ?
C11' C12' H12C 109.0 . . ?
C11' C12' H12D 109.0 . . ?
C11' C12' C13' 112.76(11) . . ?
H12C C12' H12D 107.8 . . ?
C13' C12' H12C 109.0 . . ?
C13' C12' H12D 109.0 . . ?
C12' C13' H13C 109.7 . . ?
C12' C13' H13D 109.7 . . ?
H13C C13' H13D 108.2 . . ?
C14' C13' C12' 110.02(11) . . ?
C14' C13' H13C 109.7 . . ?
C14' C13' H13D 109.7 . . ?
O15' C14' C13' 114.80(11) . . ?
O14' C14' C13' 122.17(12) . . ?
O14' C14' O15' 122.99(12) . . ?
C14' O15' H15' 109.5 . . ?

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
_geom_hbond_publ_flag
N9 H9 N3' 0.88 1.87 2.7472(15) 171.8 . yes
N6 H6 O14' 0.88 1.99 2.8543(14) 165.7 4_545 yes
O15 H15 N7' 0.84 1.85 2.6790(14) 166.7 4 yes
N9' H9' N3 0.88 2.11 2.9700(15) 164.7 . yes
N6' H6' O14 0.88 1.99 2.8508(14) 165.4 4_656 yes
O15' H15' N7 0.84 1.87 2.7038(14) 170.0 4_646 yes

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
N1 C2 N3 C4 0.6(2) . . . . ?
N1 C6 N6 C10 -5.34(19) . . . . ?
C2 N1 C6 C5 -1.74(17) . . . . ?
C2 N1 C6 N6 178.06(12) . . . . ?
C2 N3 C4 C5 -0.15(18) . . . . ?
C2 N3 C4 N9 179.67(12) . . . . ?
N3 C4 C5 C6 -1.13(19) . . . . ?
N3 C4 C5 N7 179.85(11) . . . . ?
N3 C4 N9 C8 -179.76(12) . . . . ?
C4 C5 C6 N1 2.05(17) . . . . ?
C4 C5 C6 N6 -177.75(11) . . . . ?
C4 C5 N7 C8 -0.10(14) . . . . ?
C5 C4 N9 C8 0.09(13) . . . . ?
C5 C6 N6 C10 174.45(11) . . . . ?
C5 N7 C8 N9 0.16(14) . . . . ?
C6 N1 C2 N3 0.4(2) . . . . ?
C6 C5 N7 C8 -178.91(13) . . . . ?
C6 N6 C10 C11 -154.95(12) . . . . ?
N7 C5 C6 N1 -179.20(12) . . . . ?
N7 C5 C6 N6 1.0(2) . . . . ?
N7 C8 N9 C4 -0.17(15) . . . . ?
N9 C4 C5 C6 179.02(10) . . . . ?
N9 C4 C5 N7 0.00(14) . . . . ?
N6 C10 C11 C12 66.00(14) . . . . ?
C10 C11 C12 C13 -175.53(10) . . . . ?
C11 C12 C13 C14 -179.38(10) . . . . ?
C12 C13 C14 O15 97.43(12) . . . . ?
C12 C13 C14 O14 -79.55(15) . . . . ?
N1' C2' N3' C4' -0.76(19) . . . . ?
N1' C6' N6' C10' -0.64(18) . . . . ?
C2' N1' C6' C5' 1.64(17) . . . . ?
C2' N1' C6' N6' -178.38(11) . . . . ?
C2' N3' C4' C5' -0.47(18) . . . . ?
C2' N3' C4' N9' -179.15(12) . . . . ?
N3' C4' C5' C6' 2.13(19) . . . . ?
N3' C4' C5' N7' -178.30(11) . . . . ?
N3' C4' N9' C8' 178.40(12) . . . . ?
C4' C5' C6' N1' -2.62(17) . . . . ?
C4' C5' C6' N6' 177.40(11) . . . . ?
C4' C5' N7' C8' -0.48(13) . . . . ?
C5' C4' N9' C8' -0.50(13) . . . . ?
C5' C6' N6' C10' 179.33(11) . . . . ?
C5' N7' C8' N9' 0.15(14) . . . . ?
C6' N1' C2' N3' 0.1(2) . . . . ?
C6' C5' N7' C8' 179.01(13) . . . . ?
C6' N6' C10' C11' 162.00(11) . . . . ?
N7' C5' C6' N1' 177.92(12) . . . . ?
N7' C5' C6' N6' -2.1(2) . . . . ?
N7' C8' N9' C4' 0.22(14) . . . . ?
N9' C4' C5' C6' -178.96(10) . . . . ?
N9' C4' C5' N7' 0.62(13) . . . . ?
N6' C10' C11' C12' -66.62(14) . . . . ?
C10' C11' C12' C13' 170.62(11) . . . . ?
C11' C12' C13' C14' -173.89(11) . . . . ?
C12' C13' C14' O15' -95.46(13) . . . . ?
C12' C13' C14' O14' 82.26(17) . . . . ?

_olex2_exptl_crystal_mounting_method 
'cryoloop, covered with Parabar 10320 (formerly known as Paratone)'
_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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2004251'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2020-05-16 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2020-02-09
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
miquel.barcelo@uib.es
jfa950@uib.es
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H16 N5 O2, Cl'
_chemical_formula_sum            'C11 H16 Cl N5 O2'
_chemical_formula_weight         285.74
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.3113(8)
_cell_length_b                   5.2940(4)
_cell_length_c                   20.4958(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.104(2)
_cell_angle_gamma                90
_cell_volume                     1334.93(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8494
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.58
_cell_measurement_theta_min      4.12
_shelx_estimated_absorpt_T_max   0.674
_shelx_estimated_absorpt_T_min   0.451
_exptl_absorpt_coefficient_mu    2.611
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 19903 reflections, Rint = 0.0568
 (10024 with I > 3sig(I), Rint = 0.0544)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0820
0.00 0.00 -1.00 0.0670
-1.00 -1.00 -1.00 0.1510
1.00 1.00 1.00 0.1400
0.00 -1.00 1.00 0.1790
0.00 1.00 -1.00 0.1410
1.00 0.00 0.00 0.1010
-1.00 0.00 0.00 0.0910
0.00 -1.00 -1.00 0.1760
1.00 -1.00 1.00 0.1720
-1.00 1.00 -1.00 0.1380
1.00 0.00 1.00 0.1140
-1.00 0.00 -1.00 0.1020

_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.164
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31832
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.586
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_min         4.317
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2325
_reflns_number_total             2330
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.137
_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)+(0.0915P)²+0.6279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C8(H8), N6(H6), N9(H9)
2.c Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.87505(14) 0.7595(4) 0.31889(9) 0.0395(4) Uani 1 1 d . . . . .
H1 H 0.864429 0.777123 0.276438 0.047 Uiso 1 1 calc R U . . .
C2 C 0.94178(18) 0.9267(4) 0.35064(12) 0.0420(5) Uani 1 1 d . . . . .
H2 H 0.977759 1.047992 0.324979 0.050 Uiso 1 1 calc R U . . .
N3 N 0.96036(15) 0.9336(4) 0.41386(10) 0.0428(5) Uani 1 1 d . . . . .
C4 C 0.90739(16) 0.7466(4) 0.44556(10) 0.0397(5) Uani 1 1 d . . . . .
C5 C 0.84241(17) 0.5609(4) 0.41729(11) 0.0402(5) Uani 1 1 d . . . . .
C6 C 0.82353(17) 0.5662(4) 0.34885(11) 0.0391(5) Uani 1 1 d . . . . .
N7 N 0.80131(15) 0.4065(4) 0.46523(9) 0.0422(5) Uani 1 1 d . . . . .
C8 C 0.84228(18) 0.5022(5) 0.52055(11) 0.0434(5) Uani 1 1 d . . . . .
H8 H 0.828289 0.434825 0.562370 0.052 Uiso 1 1 calc R U . . .
N6 N 0.76019(15) 0.4089(4) 0.31552(9) 0.0410(5) Uani 1 1 d . . . . .
H6 H 0.733550 0.278051 0.336045 0.049 Uiso 1 1 calc R U . . .
C10 C 0.73154(19) 0.4405(5) 0.24554(11) 0.0439(6) Uani 1 1 d . . . . .
H10A H 0.796964 0.413388 0.219744 0.053 Uiso 1 1 calc R U . . .
H10B H 0.705613 0.615111 0.237463 0.053 Uiso 1 1 calc R U . . .
C11 C 0.64365(18) 0.2549(5) 0.22355(11) 0.0442(5) Uani 1 1 d . . . . .
H11A H 0.583244 0.261870 0.254079 0.053 Uiso 1 1 calc R U . . .
H11B H 0.673693 0.081447 0.224615 0.053 Uiso 1 1 calc R U . . .
C12 C 0.60033(18) 0.3151(5) 0.15469(11) 0.0464(6) Uani 1 1 d . . . . .
H12A H 0.567559 0.485887 0.154289 0.056 Uiso 1 1 calc R U . . .
H12B H 0.661616 0.316746 0.124742 0.056 Uiso 1 1 calc R U . . .
C13 C 0.51567(19) 0.1249(5) 0.12996(12) 0.0468(6) Uani 1 1 d . . . . .
H13A H 0.462530 0.096858 0.164324 0.056 Uiso 1 1 calc R U . . .
H13B H 0.552078 -0.038178 0.121768 0.056 Uiso 1 1 calc R U . . .
C14 C 0.45467(18) 0.2098(5) 0.06724(11) 0.0449(5) Uani 1 1 d . . . . .
H14A H 0.508237 0.264850 0.035301 0.054 Uiso 1 1 calc R U . . .
H14B H 0.414583 0.063652 0.048214 0.054 Uiso 1 1 calc R U . . .
C15 C 0.37610(18) 0.4208(5) 0.07757(12) 0.0445(6) Uani 1 1 d . . . . .
O15 O 0.35035(13) 0.4940(4) 0.13113(8) 0.0485(4) Uani 1 1 d . . . . .
O16 O 0.33574(13) 0.5157(4) 0.02225(8) 0.0492(4) Uani 1 1 d . . . . .
H16 H 0.290567 0.629330 0.030373 0.074 Uiso 1 1 calc R U . . .
N9 N 0.90631(14) 0.7065(4) 0.51120(9) 0.0432(5) Uani 1 1 d . . . . .
H9 H 0.940599 0.796120 0.541699 0.052 Uiso 1 1 calc R U . . .
Cl1 Cl 0.89412(4) 0.93063(11) 0.17907(2) 0.0448(2) 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
N1 H1 0.8800 . ?
N1 C2 1.357(3) . ?
N1 C6 1.362(3) . ?
C2 H2 0.9500 . ?
C2 N3 1.308(3) . ?
N3 C4 1.363(3) . ?
C4 C5 1.381(3) . ?
C4 N9 1.363(3) . ?
C5 C6 1.414(3) . ?
C5 N7 1.388(3) . ?
C6 N6 1.315(3) . ?
N7 C8 1.325(3) . ?
C8 H8 0.9500 . ?
C8 N9 1.356(3) . ?
N6 H6 0.8800 . ?
N6 C10 1.474(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.518(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.523(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.532(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.498(3) . ?
C15 O15 1.217(3) . ?
C15 O16 1.321(3) . ?
O16 H16 0.8400 . ?
N9 H9 0.8800 . ?

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 H1 118.1 . . ?
C2 N1 C6 123.87(19) . . ?
C6 N1 H1 118.1 . . ?
N1 C2 H2 117.5 . . ?
N3 C2 N1 125.0(2) . . ?
N3 C2 H2 117.5 . . ?
C2 N3 C4 112.49(19) . . ?
N3 C4 C5 126.6(2) . . ?
N9 C4 N3 127.3(2) . . ?
N9 C4 C5 106.07(19) . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 N7 110.04(19) . . ?
N7 C5 C6 131.5(2) . . ?
N1 C6 C5 113.57(19) . . ?
N6 C6 N1 121.2(2) . . ?
N6 C6 C5 125.1(2) . . ?
C8 N7 C5 104.09(19) . . ?
N7 C8 H8 123.5 . . ?
N7 C8 N9 112.9(2) . . ?
N9 C8 H8 123.5 . . ?
C6 N6 H6 118.3 . . ?
C6 N6 C10 123.4(2) . . ?
C10 N6 H6 118.3 . . ?
N6 C10 H10A 109.4 . . ?
N6 C10 H10B 109.4 . . ?
N6 C10 C11 110.98(19) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C10 C11 C12 111.2(2) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 112.5(2) . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C12 C13 C14 113.2(2) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 C13 113.5(2) . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
O15 C15 C14 123.8(2) . . ?
O15 C15 O16 123.4(2) . . ?
O16 C15 C14 112.8(2) . . ?
C15 O16 H16 109.5 . . ?
C4 N9 H9 126.6 . . ?
C8 N9 C4 106.89(18) . . ?
C8 N9 H9 126.6 . . ?

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
_geom_hbond_publ_flag
N1 H1 Cl1 0.88 2.20 3.0227(19) 156.0 . yes
C2 H2 Cl1 0.95 2.57 3.415(2) 148.2 2_755 yes
C8 H8 Cl1 0.95 2.60 3.307(2) 131.9 4_576 yes
N6 H6 O15 0.88 1.96 2.825(3) 168.4 2_645 yes
O16 H16 N7 0.84 1.86 2.688(3) 169.9 2_655 yes
N9 H9 N3 0.88 2.07 2.915(3) 160.9 3_776 yes

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
N1 C2 N3 C4 1.9(3) . . . . ?
N1 C6 N6 C10 -5.8(3) . . . . ?
C2 N1 C6 C5 2.5(3) . . . . ?
C2 N1 C6 N6 -179.6(2) . . . . ?
C2 N3 C4 C5 1.5(3) . . . . ?
C2 N3 C4 N9 -177.5(2) . . . . ?
N3 C4 C5 C6 -2.9(3) . . . . ?
N3 C4 C5 N7 -179.2(2) . . . . ?
N3 C4 N9 C8 179.2(2) . . . . ?
C4 C5 C6 N1 0.8(3) . . . . ?
C4 C5 C6 N6 -177.1(2) . . . . ?
C4 C5 N7 C8 -0.1(3) . . . . ?
C5 C4 N9 C8 0.1(2) . . . . ?
C5 C6 N6 C10 171.8(2) . . . . ?
C5 N7 C8 N9 0.1(3) . . . . ?
C6 N1 C2 N3 -4.2(4) . . . . ?
C6 C5 N7 C8 -175.7(2) . . . . ?
C6 N6 C10 C11 -170.9(2) . . . . ?
N7 C5 C6 N1 176.1(2) . . . . ?
N7 C5 C6 N6 -1.7(4) . . . . ?
N7 C8 N9 C4 -0.1(3) . . . . ?
N6 C10 C11 C12 170.5(2) . . . . ?
C10 C11 C12 C13 177.3(2) . . . . ?
C11 C12 C13 C14 168.3(2) . . . . ?
C12 C13 C14 C15 -72.0(3) . . . . ?
C13 C14 C15 O15 -10.4(3) . . . . ?
C13 C14 C15 O16 171.0(2) . . . . ?
N9 C4 C5 C6 176.27(19) . . . . ?
N9 C4 C5 N7 0.0(2) . . . . ?

_olex2_date_sample_data_collection 2019-12-19
_olex2_date_sample_submission    2019-12-16
_olex2_exptl_crystal_mounting_method 
'cryoloop, covered with Parabar 10312 (previously known as Paratone)'
_olex2_submission_original_sample_id mb191219
_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_1_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2004252'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2020-06-17 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2020-06-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
miquel.barcelo@uib.es
jfa950@uib.es
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N5 O2, H2 O'
_chemical_formula_sum            'C14 H21 N5 O3'
_chemical_formula_weight         307.36
_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 0.0181 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3472(5)
_cell_length_b                   6.8033(3)
_cell_length_c                   18.2781(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.2710(10)
_cell_angle_gamma                90
_cell_volume                     1457.98(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.156
_cell_measurement_theta_min      3.830
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.8482.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 1.00 -1.00 0.0960
-1.00 -1.00 1.00 0.0600
1.00 0.00 1.00 0.0520
0.00 0.00 1.00 0.0430
0.00 0.00 -1.00 0.0140
1.00 0.00 -1.00 0.0640
1.00 1.00 1.00 0.1020
-1.00 0.00 -1.00 0.0050
-1.00 0.00 0.00 0.0090
1.00 -1.00 -1.00 0.0680
-1.00 1.00 1.00 0.0850
-1.00 0.00 1.00 0.0200

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.082
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15779
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.508
_diffrn_reflns_theta_max         66.508
_diffrn_reflns_theta_min         3.831
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2461
_reflns_number_total             2559
_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       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.4712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0943
_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 O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8)
2.d Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N1 N 0.60168(8) 0.72629(15) 0.49166(6) 0.0221(2) Uani 1 1 d . . . . .
C2 C 0.50380(10) 0.77315(18) 0.43813(7) 0.0226(3) Uani 1 1 d . . . . .
H2 H 0.473990 0.898943 0.443792 0.027 Uiso 1 1 calc R U . . .
N3 N 0.44173(8) 0.66866(15) 0.37773(6) 0.0225(2) Uani 1 1 d . . . . .
C4 C 0.49026(9) 0.49273(17) 0.37434(6) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.59275(9) 0.42640(17) 0.42431(6) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.64918(9) 0.54954(17) 0.48683(6) 0.0203(3) Uani 1 1 d . . . . .
N7 N 0.61532(8) 0.23805(15) 0.40325(6) 0.0227(2) Uani 1 1 d . . . . .
C8 C 0.52663(10) 0.19705(18) 0.34266(7) 0.0236(3) Uani 1 1 d . . . . .
H8 H 0.518119 0.075841 0.315634 0.028 Uiso 1 1 calc R U . . .
N9 N 0.44888(8) 0.34414(15) 0.32265(6) 0.0225(2) Uani 1 1 d . . . . .
N6 N 0.74634(8) 0.49459(16) 0.54074(6) 0.0211(2) Uani 1 1 d . . . . .
C10 C 0.80190(9) 0.60766(17) 0.60998(6) 0.0205(3) Uani 1 1 d . . . . .
H10A H 0.806634 0.525915 0.655694 0.025 Uiso 1 1 calc R U . . .
H10B H 0.754389 0.723892 0.611452 0.025 Uiso 1 1 calc R U . . .
C11 C 0.92272(9) 0.67732(17) 0.61488(6) 0.0194(3) Uani 1 1 d . . . . .
C12 C 1.00074(9) 0.49742(17) 0.61940(7) 0.0214(3) Uani 1 1 d . . . . .
H12A H 0.993002 0.407669 0.660106 0.026 Uiso 1 1 calc R U . . .
H12B H 0.974722 0.425747 0.569805 0.026 Uiso 1 1 calc R U . . .
C13 C 1.12691(10) 0.55129(18) 0.63670(7) 0.0247(3) Uani 1 1 d . . . . .
H13A H 1.172698 0.429563 0.642133 0.030 Uiso 1 1 calc R U . . .
H13B H 1.136714 0.627564 0.593081 0.030 Uiso 1 1 calc R U . . .
C14 C 1.17030(10) 0.67268(19) 0.71076(7) 0.0263(3) Uani 1 1 d . . . . .
H14A H 1.171371 0.589449 0.755405 0.032 Uiso 1 1 calc R U . . .
H14B H 1.249409 0.716076 0.717625 0.032 Uiso 1 1 calc R U . . .
C15 C 1.09536(10) 0.85231(18) 0.70860(7) 0.0248(3) Uani 1 1 d . . . . .
H15A H 1.103942 0.945647 0.669232 0.030 Uiso 1 1 calc R U . . .
H15B H 1.121065 0.919263 0.759219 0.030 Uiso 1 1 calc R U . . .
C16 C 0.96978(9) 0.79596(17) 0.68987(6) 0.0210(3) Uani 1 1 d . . . . .
H16A H 0.924055 0.917386 0.685694 0.025 Uiso 1 1 calc R U . . .
H16B H 0.960282 0.717586 0.733082 0.025 Uiso 1 1 calc R U . . .
C17 C 0.91825(9) 0.79666(17) 0.54208(6) 0.0208(3) Uani 1 1 d . . . . .
H17A H 0.995469 0.850001 0.549154 0.025 Uiso 1 1 calc R U . . .
H17B H 0.900630 0.704441 0.498002 0.025 Uiso 1 1 calc R U . . .
C18 C 0.83467(9) 0.96485(17) 0.52019(7) 0.0208(3) Uani 1 1 d . . . . .
O18 O 0.81532(7) 1.07989(12) 0.56602(5) 0.0270(2) Uani 1 1 d . . . . .
O19 O 0.78728(7) 0.98244(13) 0.44520(4) 0.0252(2) Uani 1 1 d . . . . .
H19 H 0.736545 1.069525 0.435978 0.038 Uiso 1 1 calc R U . . .
O1W O 0.75270(7) 0.12318(14) 0.70182(5) 0.0304(2) Uani 1 1 d G . . . .
H1WA H 0.694881 0.201900 0.684153 0.046 Uiso 1 1 d G U . . .
H1WB H 0.772600 0.092631 0.661592 0.046 Uiso 1 1 d G U . . .
H9 H 0.3813(15) 0.342(3) 0.2798(10) 0.046(5) Uiso 1 1 d . . . . .
H6 H 0.7629(12) 0.378(2) 0.5410(8) 0.022(3) 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
N1 C2 1.3335(15) . ?
N1 C6 1.3529(16) . ?
C2 H2 0.9500 . ?
C2 N3 1.3345(15) . ?
N3 C4 1.3486(16) . ?
C4 C5 1.3837(16) . ?
C4 N9 1.3686(15) . ?
C5 C6 1.4120(16) . ?
C5 N7 1.3911(16) . ?
C6 N6 1.3449(15) . ?
N7 C8 1.3202(15) . ?
C8 H8 0.9500 . ?
C8 N9 1.3552(16) . ?
N9 H9 0.949(18) . ?
N6 C10 1.4559(15) . ?
N6 H6 0.820(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5408(15) . ?
C11 C12 1.5437(15) . ?
C11 C16 1.5389(15) . ?
C11 C17 1.5449(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5338(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5318(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5258(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5282(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5085(16) . ?
C18 O18 1.2235(15) . ?
C18 O19 1.3161(14) . ?
O19 H19 0.8400 . ?
O1W H1WA 0.8696 . ?
O1W H1WB 0.8704 . ?

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 118.44(10) . . ?
N1 C2 H2 115.4 . . ?
N1 C2 N3 129.27(11) . . ?
N3 C2 H2 115.4 . . ?
C2 N3 C4 111.26(10) . . ?
N3 C4 C5 125.92(11) . . ?
N3 C4 N9 127.75(10) . . ?
N9 C4 C5 106.32(10) . . ?
C4 C5 C6 117.25(11) . . ?
C4 C5 N7 109.80(10) . . ?
N7 C5 C6 132.82(10) . . ?
N1 C6 C5 117.79(10) . . ?
N6 C6 N1 120.30(10) . . ?
N6 C6 C5 121.91(11) . . ?
C8 N7 C5 103.97(10) . . ?
N7 C8 H8 123.2 . . ?
N7 C8 N9 113.67(11) . . ?
N9 C8 H8 123.2 . . ?
C4 N9 H9 128.5(11) . . ?
C8 N9 C4 106.23(9) . . ?
C8 N9 H9 125.2(11) . . ?
C6 N6 C10 123.99(10) . . ?
C6 N6 H6 115.9(10) . . ?
C10 N6 H6 117.2(10) . . ?
N6 C10 H10A 108.9 . . ?
N6 C10 H10B 108.9 . . ?
N6 C10 C11 113.37(9) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 C12 109.62(9) . . ?
C10 C11 C17 109.83(9) . . ?
C12 C11 C17 108.42(9) . . ?
C16 C11 C10 107.54(9) . . ?
C16 C11 C12 108.24(9) . . ?
C16 C11 C17 113.14(9) . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.46(10) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 C12 111.24(10) . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.58(10) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C14 C15 C16 111.67(10) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C11 C16 H16A 108.8 . . ?
C11 C16 H16B 108.8 . . ?
C15 C16 C11 113.86(9) . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C11 C17 H17A 107.9 . . ?
C11 C17 H17B 107.9 . . ?
H17A C17 H17B 107.2 . . ?
C18 C17 C11 117.64(9) . . ?
C18 C17 H17A 107.9 . . ?
C18 C17 H17B 107.9 . . ?
O18 C18 C17 124.60(10) . . ?
O18 C18 O19 122.43(11) . . ?
O19 C18 C17 112.90(10) . . ?
C18 O19 H19 109.5 . . ?
H1WA O1W H1WB 104.5 . . ?

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
_geom_hbond_publ_flag
C16 H16A O18 0.99 2.44 3.1282(14) 125.9 . yes
O19 H19 N7 0.84 1.83 2.6645(13) 171.6 1_565 yes
O1W H1WA N3 0.87 1.92 2.7738(13) 165.1 3_666 yes
O1W H1WB O18 0.87 1.98 2.8372(12) 168.6 1_545 yes
N9 H9 O1W 0.949(18) 1.786(18) 2.7276(13) 171.3(16) 4_565 yes

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
N1 C2 N3 C4 0.09(17) . . . . ?
N1 C6 N6 C10 5.36(17) . . . . ?
C2 N1 C6 C5 1.02(15) . . . . ?
C2 N1 C6 N6 -178.32(10) . . . . ?
C2 N3 C4 C5 -2.01(16) . . . . ?
C2 N3 C4 N9 177.00(11) . . . . ?
N3 C4 C5 C6 3.34(17) . . . . ?
N3 C4 C5 N7 179.72(10) . . . . ?
N3 C4 N9 C8 -179.48(11) . . . . ?
C4 C5 C6 N1 -2.64(15) . . . . ?
C4 C5 C6 N6 176.69(10) . . . . ?
C4 C5 N7 C8 -0.53(12) . . . . ?
C5 C4 N9 C8 -0.32(12) . . . . ?
C5 C6 N6 C10 -173.95(10) . . . . ?
C5 N7 C8 N9 0.33(13) . . . . ?
C6 N1 C2 N3 0.32(18) . . . . ?
C6 C5 N7 C8 175.09(12) . . . . ?
C6 N6 C10 C11 -118.25(12) . . . . ?
N7 C5 C6 N1 -177.99(11) . . . . ?
N7 C5 C6 N6 1.34(19) . . . . ?
N7 C8 N9 C4 -0.01(14) . . . . ?
N9 C4 C5 C6 -175.85(10) . . . . ?
N9 C4 C5 N7 0.53(12) . . . . ?
N6 C10 C11 C12 -63.22(12) . . . . ?
N6 C10 C11 C16 179.31(9) . . . . ?
N6 C10 C11 C17 55.79(13) . . . . ?
C10 C11 C12 C13 -171.27(9) . . . . ?
C10 C11 C16 C15 172.24(10) . . . . ?
C10 C11 C17 C18 52.38(13) . . . . ?
C11 C12 C13 C14 55.46(13) . . . . ?
C11 C17 C18 O18 40.44(16) . . . . ?
C11 C17 C18 O19 -142.60(10) . . . . ?
C12 C11 C16 C15 53.88(13) . . . . ?
C12 C11 C17 C18 172.13(9) . . . . ?
C12 C13 C14 C15 -53.49(14) . . . . ?
C13 C14 C15 C16 53.15(14) . . . . ?
C14 C15 C16 C11 -54.81(13) . . . . ?
C16 C11 C12 C13 -54.24(12) . . . . ?
C16 C11 C17 C18 -67.79(13) . . . . ?
C17 C11 C12 C13 68.85(12) . . . . ?
C17 C11 C16 C15 -66.30(12) . . . . ?

_olex2_exptl_crystal_mounting_method 
'cryoloop, covered with Parabar 10320 (formally known as Paratone)'
_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2004250'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2020-05-16 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_date             2019-04-04T14:55:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C11 H15 N5 O2'
_chemical_formula_sum            'C11 H15 N5 O2'
_chemical_formula_weight         249.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.159(4)
_cell_length_b                   9.126(4)
_cell_length_c                   9.472(4)
_cell_angle_alpha                102.47(4)
_cell_angle_beta                 91.989(9)
_cell_angle_gamma                98.392(9)
_cell_volume                     596.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2152
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS - Bruker/Siemens area detector absorption and other corrections -
;
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.981

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.116647
_diffrn_orient_matrix_ub_12      0.033745
_diffrn_orient_matrix_ub_13      0.01344
_diffrn_orient_matrix_ub_21      0.079339
_diffrn_orient_matrix_ub_22      0.065543
_diffrn_orient_matrix_ub_23      0.037271
_diffrn_orient_matrix_ub_31      0.011467
_diffrn_orient_matrix_ub_32      0.045902
_diffrn_orient_matrix_ub_33      -0.056732
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_number            2418
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             2418
_reflns_number_gt                1858
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V6.28A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2017/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0687P)²+0.1609P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2418
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0288(2) 0.7684(2) 1.03015(18) 0.0365(4) Uani 1 1 d . . . . .
C2 C -0.1681(3) 0.8289(2) 1.1010(2) 0.0383(5) Uani 1 1 d . . . . .
H2 H -0.173607 0.821164 1.197114 0.046 Uiso 1 1 calc R U . . .
N3 N -0.2996(2) 0.8985(2) 1.05238(18) 0.0357(4) Uani 1 1 d . . . . .
C4 C -0.2824(3) 0.9026(2) 0.9124(2) 0.0301(4) Uani 1 1 d . . . . .
C5 C -0.1466(3) 0.8461(2) 0.8263(2) 0.0311(5) Uani 1 1 d . . . . .
C6 C -0.0133(3) 0.7769(2) 0.8909(2) 0.0322(5) Uani 1 1 d . . . . .
N6 N 0.1246(2) 0.7178(2) 0.81766(19) 0.0397(5) Uani 1 1 d . . . . .
H6 H 0.133127 0.726881 0.729526 0.06 Uiso 1 1 calc R U . . .
N7 N -0.1759(2) 0.8674(2) 0.68751(18) 0.0370(4) Uani 1 1 d . . . . .
C8 C -0.3261(3) 0.9344(2) 0.6934(2) 0.0375(5) Uani 1 1 d . . . . .
H8 H -0.379632 0.962138 0.614086 0.045 Uiso 1 1 calc R U . . .
N9 N -0.3957(2) 0.9595(2) 0.82554(18) 0.0357(4) Uani 1 1 d . . . . .
H9 H -0.500(3) 1.0060(13) 0.8521(8) 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2612(3) 0.6392(2) 0.8763(2) 0.0363(5) Uani 1 1 d . . . . .
H10A H 0.196366 0.563376 0.922839 0.044 Uiso 1 1 calc R U . . .
H10B H 0.348624 0.711034 0.947985 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3676(3) 0.5641(3) 0.7532(2) 0.0409(5) Uani 1 1 d . . . . .
H11A H 0.423319 0.641001 0.704055 0.049 Uiso 1 1 calc R U . . .
H11B H 0.277602 0.4914 0.684157 0.049 Uiso 1 1 calc R U . . .
C12 C 0.5229(3) 0.4825(2) 0.7965(2) 0.0365(5) Uani 1 1 d . . . . .
H12A H 0.61919 0.555172 0.859882 0.044 Uiso 1 1 calc R U . . .
H12B H 0.470455 0.40798 0.849479 0.044 Uiso 1 1 calc R U . . .
C13 C 0.6115(4) 0.4041(3) 0.6642(3) 0.0554(7) Uani 1 1 d . . . . .
H13A H 0.517189 0.323144 0.608514 0.066 Uiso 1 1 calc R U . . .
H13B H 0.64405 0.476722 0.60443 0.066 Uiso 1 1 calc R U . . .
C14 C 0.7841(3) 0.3380(3) 0.6929(2) 0.0439(6) Uani 1 1 d . . . . .
H14A H 0.75589 0.271603 0.75927 0.053 Uiso 1 1 calc R U . . .
H14B H 0.883804 0.419634 0.739756 0.053 Uiso 1 1 calc R U . . .
C15 C 0.8540(3) 0.2498(3) 0.5581(2) 0.0380(5) Uani 1 1 d . . . . .
O15 O 0.7512(2) 0.1817(2) 0.45348(17) 0.0534(5) Uani 1 1 d . . . . .
O16 O 1.0369(2) 0.2516(2) 0.56383(18) 0.0587(5) Uani 1 1 d . . . . .
H16 H 1.067945 0.209496 0.484585 0.088 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.340(3) . ?
N1 C6 1.345(3) . ?
C2 N3 1.332(2) . ?
C2 H2 0.93 . ?
N3 C4 1.344(3) . ?
C4 N9 1.365(3) . ?
C4 C5 1.377(3) . ?
C5 N7 1.383(3) . ?
C5 C6 1.410(3) . ?
C6 N6 1.337(2) . ?
N6 C10 1.455(2) . ?
N6 H6 0.86 . ?
N7 C8 1.310(2) . ?
C8 N9 1.349(3) . ?
C8 H8 0.93 . ?
N9 H9 0.93(3) . ?
C10 C11 1.510(3) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C12 1.517(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.512(3) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.493(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 C15 1.499(3) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 O15 1.208(3) . ?
C15 O16 1.307(3) . ?
O16 H16 0.82 . ?

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 118.25(17) . . ?
N3 C2 N1 128.76(19) . . ?
N3 C2 H2 115.6 . . ?
N1 C2 H2 115.6 . . ?
C2 N3 C4 111.55(16) . . ?
N3 C4 N9 127.90(16) . . ?
N3 C4 C5 126.16(17) . . ?
N9 C4 C5 105.92(17) . . ?
C4 C5 N7 109.98(17) . . ?
C4 C5 C6 116.93(18) . . ?
N7 C5 C6 133.07(17) . . ?
N6 C6 N1 119.55(18) . . ?
N6 C6 C5 122.11(18) . . ?
N1 C6 C5 118.33(17) . . ?
C6 N6 C10 124.71(17) . . ?
C6 N6 H6 117.6 . . ?
C10 N6 H6 117.6 . . ?
C8 N7 C5 104.17(16) . . ?
N7 C8 N9 113.50(19) . . ?
N7 C8 H8 123.2 . . ?
N9 C8 H8 123.2 . . ?
C8 N9 C4 106.43(16) . . ?
C8 N9 H9 126.8 . . ?
C4 N9 H9 126.8 . . ?
N6 C10 C11 108.39(16) . . ?
N6 C10 H10A 110 . . ?
C11 C10 H10A 110 . . ?
N6 C10 H10B 110 . . ?
C11 C10 H10B 110 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 C12 115.34(17) . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 110.67(17) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 115.89(19) . . ?
C14 C13 H13A 108.3 . . ?
C12 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 C15 113.04(18) . . ?
C13 C14 H14A 109 . . ?
C15 C14 H14A 109 . . ?
C13 C14 H14B 109 . . ?
C15 C14 H14B 109 . . ?
H14A C14 H14B 107.8 . . ?
O15 C15 O16 122.59(19) . . ?
O15 C15 C14 123.43(19) . . ?
O16 C15 C14 113.98(19) . . ?
C15 O16 H16 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
C6 N1 C2 N3 0.3(3) . . . . ?
N1 C2 N3 C4 0.9(3) . . . . ?
C2 N3 C4 N9 177.36(19) . . . . ?
C2 N3 C4 C5 -1.1(3) . . . . ?
N3 C4 C5 N7 178.59(19) . . . . ?
N9 C4 C5 N7 -0.2(2) . . . . ?
N3 C4 C5 C6 0.2(3) . . . . ?
N9 C4 C5 C6 -178.51(17) . . . . ?
C2 N1 C6 N6 179.84(18) . . . . ?
C2 N1 C6 C5 -1.3(3) . . . . ?
C4 C5 C6 N6 179.87(18) . . . . ?
N7 C5 C6 N6 2.0(4) . . . . ?
C4 C5 C6 N1 1.0(3) . . . . ?
N7 C5 C6 N1 -176.9(2) . . . . ?
N1 C6 N6 C10 1.6(3) . . . . ?
C5 C6 N6 C10 -177.22(19) . . . . ?
C4 C5 N7 C8 -0.2(2) . . . . ?
C6 C5 N7 C8 177.8(2) . . . . ?
C5 N7 C8 N9 0.5(2) . . . . ?
N7 C8 N9 C4 -0.6(2) . . . . ?
N3 C4 N9 C8 -178.3(2) . . . . ?
C5 C4 N9 C8 0.4(2) . . . . ?
C6 N6 C10 C11 169.22(19) . . . . ?
N6 C10 C11 C12 177.33(18) . . . . ?
C10 C11 C12 C13 176.6(2) . . . . ?
C11 C12 C13 C14 171.7(2) . . . . ?
C12 C13 C14 C15 174.7(2) . . . . ?
C13 C14 C15 O15 -30.9(3) . . . . ?
C13 C14 C15 O16 149.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6 O15 0.86 2.22 3.028(3) 157 2_666 yes
N9 H9 N3 0.93 1.94 2.851(2) 168 2_477 yes
C11 H11B O16 0.97 2.6 3.532(3) 162 1_455 yes
O16 H16 N7 0.82 1.87 2.683(2) 171 2_666 yes



# END of CIF


