# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
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data_nvp_ba_a
_database_code_depnum_ccdc_archive 'CCDC 2012053'
loop_
_audit_author_name
_audit_author_address
'Lourdes Infantes'
;Instituto Quimica Fisica Rocasolano, CSIC
Spain
;
_audit_update_record             
;
2020-06-24 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2018-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled Feb 23 2017 12:17:46 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N4 O, C7 H6 O2'
_chemical_formula_sum            'C22 H20 N4 O3'
_chemical_formula_weight         388.42
_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 0.0033 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'

_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        P2(1)/c
_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                   9.934(2)
_cell_length_b                   8.360(2)
_cell_length_c                   23.571(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.977(8)
_cell_angle_gamma                90
_cell_volume                     1954.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    4106
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      24.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.745162
_exptl_absorpt_correction_T_min  0.577417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16929
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.069
_diffrn_reflns_theta_max         25.069
_diffrn_reflns_theta_min         2.585
_diffrn_ambient_temperature      299.8
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1957
_reflns_number_total             3441
_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, 2016)'
_computing_data_collection       'Bruker Apex3, 2019'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0116(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.039
_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)+(0.0371P)²+1.0895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1396
_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 C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O1B)
Uanis(C1A) = Uanis(C1B)
Uanis(N1A) = Uanis(N1B)
Uanis(C12A) = Uanis(C12B)
3. Same fragment restrains
{O1A, N1A, C1A, C12A} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1B, N1B, C1B, C12B}
4. Others
 Sof(O1B)=Sof(N1B)=Sof(H1B)=Sof(C1B)=Sof(C12B)=Sof(H12D)=Sof(H12E)=Sof(H12F)=
 Sof(H10)=1-FVAR(1)
 Sof(O1A)=Sof(N1A)=Sof(H1A)=Sof(C1A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=
 Sof(H3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
5.c Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1B(H1B), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
5.d Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
5.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1A O 0.4262(3) 0.1689(3) 0.47973(12) 0.0483(8) Uani 0.720(3) 1 d D . P A 1
N1A N 0.4427(4) -0.0308(9) 0.4169(2) 0.0326(14) Uani 0.720(3) 1 d D . P A 1
H1A H 0.458219 -0.094549 0.445095 0.039 Uiso 0.720(3) 1 calc R . P A 1
C1A C 0.4074(11) 0.1210(7) 0.4302(4) 0.0366(17) Uani 0.720(3) 1 d D . P A 1
C12A C 0.6831(4) -0.2114(6) 0.3935(2) 0.0606(13) Uani 0.720(3) 1 d D . P A 1
H12A H 0.649310 -0.264641 0.425956 0.091 Uiso 0.720(3) 1 calc GR . P A 1
H12B H 0.717940 -0.108363 0.404727 0.091 Uiso 0.720(3) 1 calc GR . P A 1
H12C H 0.753726 -0.274294 0.378438 0.091 Uiso 0.720(3) 1 calc GR . P A 1
O1B O 0.5315(7) -0.1276(8) 0.4522(3) 0.0483(8) Uani 0.280(3) 1 d D . P A 2
N1B N 0.404(2) 0.084(2) 0.4294(10) 0.0326(14) Uani 0.280(3) 1 d D . P A 2
H1B H 0.388315 0.097231 0.464704 0.039 Uiso 0.280(3) 1 calc R . P A 2
C1B C 0.474(2) -0.048(3) 0.4172(10) 0.0366(17) Uani 0.280(3) 1 d D . P A 2
C12B C 0.4548(11) 0.4214(15) 0.4535(5) 0.0606(13) Uani 0.280(3) 1 d D . P A 2
H12D H 0.405894 0.391868 0.485952 0.091 Uiso 0.280(3) 1 calc GR . P A 2
H12E H 0.475240 0.533596 0.455149 0.091 Uiso 0.280(3) 1 calc GR . P A 2
H12F H 0.537179 0.361302 0.453431 0.091 Uiso 0.280(3) 1 calc GR . P A 2
O2 O 0.3442(3) -0.2895(4) 0.13341(11) 0.1071(12) Uani 1 1 d . . . . .
O3 O 0.1877(2) -0.1382(3) 0.16841(10) 0.0702(7) Uani 1 1 d . . . . .
H3A H 0.237188 -0.146580 0.197196 0.105 Uiso 1 1 calc GR . . . .
N2 N 0.2374(2) 0.0075(3) 0.33073(9) 0.0349(6) Uani 1 1 d . . . . .
N3 N 0.1970(2) 0.2751(3) 0.30698(10) 0.0470(7) Uani 1 1 d . . . . .
N4 N 0.3549(2) -0.1551(3) 0.26848(10) 0.0425(6) Uani 1 1 d . . . . .
C2 C 0.3453(3) 0.2202(3) 0.38759(12) 0.0376(7) Uani 1 1 d . . . . .
C3 C 0.3644(3) 0.3834(4) 0.39618(15) 0.0534(9) Uani 1 1 d . . . . .
H3 H 0.420168 0.420371 0.426274 0.064 Uiso 0.720(3) 1 calc R . P A 1
C4 C 0.2996(3) 0.4890(4) 0.35958(16) 0.0617(10) Uani 1 1 d . . . . .
H4 H 0.311724 0.598725 0.364001 0.074 Uiso 1 1 calc R . . . .
C5 C 0.2173(4) 0.4303(4) 0.31676(15) 0.0589(10) Uani 1 1 d . . . . .
H5 H 0.172281 0.503041 0.292729 0.071 Uiso 1 1 calc R . . . .
C6 C 0.2621(3) 0.1720(3) 0.34185(11) 0.0355(7) Uani 1 1 d . . . . .
C7 C 0.3522(3) -0.0841(3) 0.31957(12) 0.0344(7) Uani 1 1 d . . . . .
C8 C 0.4626(3) -0.2445(4) 0.25803(14) 0.0546(9) Uani 1 1 d . . . . .
H8 H 0.464291 -0.296454 0.223177 0.066 Uiso 1 1 calc R . . . .
C9 C 0.5706(3) -0.2635(4) 0.29613(14) 0.0554(9) Uani 1 1 d . . . . .
H9 H 0.644010 -0.325329 0.286724 0.066 Uiso 1 1 calc R . . . .
C10 C 0.5693(3) -0.1905(4) 0.34827(13) 0.0465(8) Uani 1 1 d . . . . .
H10 H 0.641364 -0.201832 0.374761 0.056 Uiso 0.280(3) 1 calc R . P A 2
C11 C 0.4576(3) -0.0991(3) 0.36045(12) 0.0368(7) Uani 1 1 d . . . . .
C13 C 0.1141(3) -0.0294(3) 0.29755(12) 0.0413(8) Uani 1 1 d . . . . .
H13 H 0.108786 0.003740 0.257614 0.050 Uiso 1 1 calc R . . . .
C14 C 0.0432(3) -0.1790(4) 0.31224(14) 0.0536(9) Uani 1 1 d . . . . .
H14A H 0.084303 -0.245811 0.341998 0.064 Uiso 1 1 calc R . . . .
H14B H -0.004700 -0.236749 0.281728 0.064 Uiso 1 1 calc R . . . .
C15 C -0.0113(3) -0.0204(4) 0.32887(14) 0.0521(9) Uani 1 1 d . . . . .
H15A H -0.092218 0.018009 0.308455 0.062 Uiso 1 1 calc R . . . .
H15B H -0.003227 0.008949 0.368716 0.062 Uiso 1 1 calc R . . . .
C16 C 0.1537(3) -0.2259(4) 0.07417(13) 0.0478(8) Uani 1 1 d . . . . .
C17 C 0.2052(4) -0.2981(5) 0.02726(15) 0.0718(11) Uani 1 1 d . . . . .
H17 H 0.292946 -0.337284 0.029498 0.086 Uiso 1 1 calc R . . . .
C18 C 0.1289(4) -0.3128(5) -0.02234(16) 0.0844(13) Uani 1 1 d . . . . .
H18 H 0.165332 -0.359448 -0.053925 0.101 Uiso 1 1 calc R . . . .
C19 C 0.0002(4) -0.2592(6) -0.02539(17) 0.0898(14) Uani 1 1 d . . . . .
H19 H -0.052059 -0.270309 -0.059048 0.108 Uiso 1 1 calc R . . . .
C20 C -0.0532(4) -0.1894(6) 0.02027(18) 0.0927(15) Uani 1 1 d . . . . .
H20 H -0.141948 -0.153523 0.017910 0.111 Uiso 1 1 calc R . . . .
C21 C 0.0243(3) -0.1714(5) 0.07041(15) 0.0670(11) Uani 1 1 d . . . . .
H21 H -0.011957 -0.122115 0.101517 0.080 Uiso 1 1 calc R . . . .
C22 C 0.2382(4) -0.2192(4) 0.12730(14) 0.0569(9) 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
O1A C1A 1.239(10) . ?
N1A H1A 0.8600 . ?
N1A C1A 1.357(6) . ?
N1A C11 1.462(7) . ?
C1A C2 1.419(9) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C12A C10 1.524(5) . ?
O1B C1B 1.185(18) . ?
N1B H1B 0.8600 . ?
N1B C1B 1.344(15) . ?
N1B C2 1.594(19) . ?
C1B C11 1.41(3) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C12B C3 1.615(11) . ?
O2 C22 1.208(4) . ?
O3 H3A 0.8200 . ?
O3 C22 1.304(4) . ?
N2 C6 1.420(3) . ?
N2 C7 1.410(3) . ?
N2 C13 1.451(3) . ?
N3 C5 1.331(4) . ?
N3 C6 1.335(3) . ?
N4 C7 1.344(3) . ?
N4 C8 1.338(4) . ?
C2 C3 1.391(4) . ?
C2 C6 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(4) . ?
C5 H5 0.9300 . ?
C7 C11 1.391(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.485(4) . ?
C13 C15 1.482(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.493(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.381(5) . ?
C16 C21 1.362(4) . ?
C16 C22 1.472(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.365(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.354(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.356(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(5) . ?
C21 H21 0.9300 . ?

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
C1A N1A H1A 116.0 . . ?
C1A N1A C11 128.0(6) . . ?
C11 N1A H1A 116.0 . . ?
O1A C1A N1A 119.5(7) . . ?
O1A C1A C2 121.1(6) . . ?
N1A C1A C2 119.4(7) . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C10 C12A H12A 109.5 . . ?
C10 C12A H12B 109.5 . . ?
C10 C12A H12C 109.5 . . ?
C1B N1B H1B 115.5 . . ?
C1B N1B C2 129(2) . . ?
C2 N1B H1B 115.5 . . ?
O1B C1B N1B 123(2) . . ?
O1B C1B C11 121(2) . . ?
N1B C1B C11 114.8(19) . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C3 C12B H12D 109.5 . . ?
C3 C12B H12E 109.5 . . ?
C3 C12B H12F 109.5 . . ?
C22 O3 H3A 109.5 . . ?
C6 N2 C13 116.0(2) . . ?
C7 N2 C6 115.3(2) . . ?
C7 N2 C13 116.9(2) . . ?
C5 N3 C6 117.3(3) . . ?
C8 N4 C7 117.7(2) . . ?
C3 C2 C1A 114.8(4) . . ?
C3 C2 N1B 124.5(8) . . ?
C6 C2 C1A 127.0(4) . . ?
C6 C2 N1B 117.3(8) . . ?
C6 C2 C3 118.0(3) . . ?
C2 C3 C12B 112.3(5) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C12B 128.5(5) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
N3 C5 C4 124.2(3) . . ?
N3 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N3 C6 N2 116.0(2) . . ?
N3 C6 C2 122.9(3) . . ?
C2 C6 N2 121.1(2) . . ?
N4 C7 N2 117.5(2) . . ?
N4 C7 C11 122.1(3) . . ?
C11 C7 N2 120.4(3) . . ?
N4 C8 H8 118.3 . . ?
N4 C8 C9 123.3(3) . . ?
C9 C8 H8 118.3 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C12A 122.3(3) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.3(3) . . ?
C11 C10 C12A 119.3(3) . . ?
C11 C10 H10 120.8 . . ?
C7 C11 N1A 119.1(3) . . ?
C7 C11 C1B 132.5(9) . . ?
C10 C11 N1A 121.5(3) . . ?
C10 C11 C1B 108.1(9) . . ?
C10 C11 C7 119.1(3) . . ?
N2 C13 H13 117.3 . . ?
N2 C13 C14 116.8(2) . . ?
N2 C13 C15 115.3(2) . . ?
C14 C13 H13 117.3 . . ?
C15 C13 H13 117.3 . . ?
C15 C13 C14 60.4(2) . . ?
C13 C14 H14A 117.8 . . ?
C13 C14 H14B 117.8 . . ?
C13 C14 C15 59.7(2) . . ?
H14A C14 H14B 114.9 . . ?
C15 C14 H14A 117.8 . . ?
C15 C14 H14B 117.8 . . ?
C13 C15 C14 59.9(2) . . ?
C13 C15 H15A 117.8 . . ?
C13 C15 H15B 117.8 . . ?
C14 C15 H15A 117.8 . . ?
C14 C15 H15B 117.8 . . ?
H15A C15 H15B 114.9 . . ?
C17 C16 C22 118.6(3) . . ?
C21 C16 C17 118.8(3) . . ?
C21 C16 C22 122.5(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(4) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.0(3) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
O2 C22 O3 122.0(3) . . ?
O2 C22 C16 122.6(3) . . ?
O3 C22 C16 115.3(3) . . ?

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
O1A C1A C2 C3 28.4(10) . . . . ?
O1A C1A C2 C6 -146.8(6) . . . . ?
N1A C1A C2 C3 -153.8(7) . . . . ?
N1A C1A C2 C6 31.0(12) . . . . ?
C1A N1A C11 C7 -52.7(10) . . . . ?
C1A N1A C11 C10 133.0(7) . . . . ?
C1A C2 C3 C4 -175.1(6) . . . . ?
C1A C2 C6 N2 -4.5(7) . . . . ?
C1A C2 C6 N3 173.0(6) . . . . ?
C12A C10 C11 N1A -3.9(6) . . . . ?
C12A C10 C11 C7 -178.2(3) . . . . ?
O1B C1B C11 C7 142.8(14) . . . . ?
O1B C1B C11 C10 -32(2) . . . . ?
N1B C1B C11 C7 -28(3) . . . . ?
N1B C1B C11 C10 156.8(19) . . . . ?
N1B C2 C3 C12B 0.7(13) . . . . ?
N1B C2 C3 C4 -174.6(12) . . . . ?
N1B C2 C6 N2 -4.0(12) . . . . ?
N1B C2 C6 N3 173.5(11) . . . . ?
C1B N1B C2 C3 -130(2) . . . . ?
C1B N1B C2 C6 55(3) . . . . ?
C12B C3 C4 C5 -173.4(6) . . . . ?
N2 C7 C11 N1A 5.4(5) . . . . ?
N2 C7 C11 C1B 5.5(15) . . . . ?
N2 C7 C11 C10 179.9(3) . . . . ?
N2 C13 C14 C15 105.4(3) . . . . ?
N2 C13 C15 C14 -107.7(3) . . . . ?
N4 C7 C11 N1A -174.5(4) . . . . ?
N4 C7 C11 C1B -174.4(15) . . . . ?
N4 C7 C11 C10 -0.1(4) . . . . ?
N4 C8 C9 C10 1.2(5) . . . . ?
C2 N1B C1B O1B 167.1(16) . . . . ?
C2 N1B C1B C11 -22(4) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C2 C6 N2 -179.6(3) . . . . ?
C3 C2 C6 N3 -2.0(4) . . . . ?
C3 C4 C5 N3 -1.5(6) . . . . ?
C5 N3 C6 N2 179.4(3) . . . . ?
C5 N3 C6 C2 1.7(4) . . . . ?
C6 N2 C7 N4 -118.7(3) . . . . ?
C6 N2 C7 C11 61.4(3) . . . . ?
C6 N2 C13 C14 -144.8(3) . . . . ?
C6 N2 C13 C15 -76.7(3) . . . . ?
C6 N3 C5 C4 0.1(5) . . . . ?
C6 C2 C3 C12B 175.9(5) . . . . ?
C6 C2 C3 C4 0.6(5) . . . . ?
C7 N2 C6 N3 121.1(3) . . . . ?
C7 N2 C6 C2 -61.2(3) . . . . ?
C7 N2 C13 C14 74.0(3) . . . . ?
C7 N2 C13 C15 142.1(3) . . . . ?
C7 N4 C8 C9 -1.7(5) . . . . ?
C8 N4 C7 N2 -178.8(3) . . . . ?
C8 N4 C7 C11 1.1(4) . . . . ?
C8 C9 C10 C12A 177.6(4) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 N1A 173.9(4) . . . . ?
C9 C10 C11 C1B 175.2(12) . . . . ?
C9 C10 C11 C7 -0.4(4) . . . . ?
C11 N1A C1A O1A -165.1(5) . . . . ?
C11 N1A C1A C2 17.1(14) . . . . ?
C13 N2 C6 N3 -20.8(4) . . . . ?
C13 N2 C6 C2 156.9(3) . . . . ?
C13 N2 C7 N4 22.8(4) . . . . ?
C13 N2 C7 C11 -157.1(3) . . . . ?
C16 C17 C18 C19 -1.5(7) . . . . ?
C17 C16 C21 C20 0.2(6) . . . . ?
C17 C16 C22 O2 -8.5(6) . . . . ?
C17 C16 C22 O3 174.7(3) . . . . ?
C17 C18 C19 C20 0.7(7) . . . . ?
C18 C19 C20 C21 0.4(8) . . . . ?
C19 C20 C21 C16 -0.9(7) . . . . ?
C21 C16 C17 C18 1.0(6) . . . . ?
C21 C16 C22 O2 167.9(4) . . . . ?
C21 C16 C22 O3 -9.0(5) . . . . ?
C22 C16 C17 C18 177.5(4) . . . . ?
C22 C16 C21 C20 -176.1(4) . . . . ?

_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_3hbzc
_database_code_depnum_ccdc_archive 'CCDC 2012054'
loop_
_audit_author_name
_audit_author_address
'Lourdes Infantes'
;CSIC
Spain
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N4 O, 0.5(C7 H6 O3)'
_chemical_formula_sum            'C18.50 H17 N4 O2.50'
_chemical_formula_weight         335.36
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2706(14)
_cell_length_b                   9.5902(19)
_cell_length_c                   11.881(2)
_cell_angle_alpha                96.11(3)
_cell_angle_beta                 92.79(3)
_cell_angle_gamma                98.34(3)
_cell_volume                     813.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9639
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      66.54
_cell_measurement_theta_min      3.75
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1423 before and 0.0948 after correction.
The Ratio of minimum to maximum transmission is 0.7707.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25432
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        66.586
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_min         3.749
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1572
_reflns_number_total             2801
_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 SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ?'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS (Sheldrick 2008)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0130(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      1.014
_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)+(0.0864P)²+0.5292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.2086
_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 C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 O1A, O2A, O3A, C1A, C2A, C3A, C4A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Others
 Fixed Sof: O2A(0.5) O1A(0.5) H1A(0.5) O3A(0.5) H3A(0.5) C1A(0.5) C2A(0.5)
 H2A(0.5) C3A(0.5) C4A(0.5) H4A(0.5) C5A(0.5) H5A(0.5) C6A(0.5) H6A(0.5)
 C7A(0.5)
4.a Riding coordinates:
 O1A(H1A)
4.b Free rotating group:
 O2A(O1A)
4.c Ternary CH refined with riding coordinates:
 C13(H13)
4.d Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
4.e Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C2A(H2A), C4A(H4A),
 C5A(H5A), C6A(H6A)
4.f Fitted hexagon refined as free rotating group:
 C1A(C2A,C3A,C4A,C5A,C6A)
4.g Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
4.h Idealised tetrahedral OH refined as rotating group:
 O3A(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8118(4) 1.0367(3) 0.4212(2) 0.0861(9) Uani 1 1 d . . . . .
N1 N 0.8441(4) 0.8137(3) 0.4527(2) 0.0673(9) Uani 1 1 d . . . . .
H1 H 0.951393 0.847013 0.486201 0.081 Uiso 1 1 calc R . . . .
N2 N 0.6791(4) 0.4367(3) 0.3501(3) 0.0722(9) Uani 1 1 d . . . . .
N3 N 0.6835(4) 0.6397(3) 0.2530(2) 0.0645(8) Uani 1 1 d . . . . .
N4 N 0.4018(5) 0.6986(3) 0.1834(3) 0.0745(9) Uani 1 1 d . . . . .
C1 C 0.7520(5) 0.9071(4) 0.4055(3) 0.0670(10) Uani 1 1 d . . . . .
C2 C 0.5754(5) 0.8551(4) 0.3356(3) 0.0646(10) Uani 1 1 d . . . . .
C3 C 0.5493(5) 0.7327(4) 0.2581(3) 0.0641(10) Uani 1 1 d . . . . .
C4 C 0.7168(5) 0.5784(4) 0.3539(3) 0.0623(9) Uani 1 1 d . . . . .
C5 C 0.7840(5) 0.6664(4) 0.4533(3) 0.0607(9) Uani 1 1 d . . . . .
C6 C 0.8033(5) 0.6064(4) 0.5547(3) 0.0670(10) Uani 1 1 d . . . . .
C7 C 0.7607(5) 0.4597(5) 0.5483(4) 0.0770(11) Uani 1 1 d . . . . .
H7 H 0.769755 0.415098 0.613751 0.092 Uiso 1 1 calc R . . . .
C8 C 0.7054(5) 0.3802(4) 0.4465(4) 0.0777(11) Uani 1 1 d . . . . .
H8 H 0.685048 0.281920 0.444294 0.093 Uiso 1 1 calc R . . . .
C9 C 0.2720(6) 0.7835(5) 0.1895(4) 0.0836(12) Uani 1 1 d . . . . .
H9 H 0.169804 0.761117 0.137198 0.100 Uiso 1 1 calc R . . . .
C10 C 0.2769(6) 0.9012(5) 0.2667(4) 0.0864(12) Uani 1 1 d . . . . .
H10 H 0.178311 0.953042 0.270298 0.104 Uiso 1 1 calc R . . . .
C11 C 0.4365(6) 0.9394(4) 0.3395(3) 0.0779(11) Uani 1 1 d . . . . .
H11 H 0.449562 1.021323 0.390473 0.093 Uiso 1 1 calc R . . . .
C12 C 0.8662(6) 0.6949(5) 0.6651(3) 0.0858(13) Uani 1 1 d . . . . .
H12A H 0.987598 0.747379 0.659282 0.129 Uiso 1 1 calc GR . . . .
H12B H 0.871422 0.634477 0.724235 0.129 Uiso 1 1 calc GR . . . .
H12C H 0.779856 0.759734 0.682581 0.129 Uiso 1 1 calc GR . . . .
C13 C 0.6826(6) 0.5484(4) 0.1472(3) 0.0795(12) Uani 1 1 d . . . . .
H13 H 0.571296 0.478160 0.125243 0.095 Uiso 1 1 calc R . . . .
C14 C 0.7806(6) 0.6156(5) 0.0548(3) 0.0919(14) Uani 1 1 d . . . . .
H14A H 0.837070 0.714245 0.070473 0.110 Uiso 1 1 calc R . . . .
H14B H 0.729843 0.586805 -0.022588 0.110 Uiso 1 1 calc R . . . .
C15 C 0.8643(6) 0.5093(5) 0.1156(4) 0.0869(13) Uani 1 1 d . . . . .
H15A H 0.864690 0.416086 0.074893 0.104 Uiso 1 1 calc R . . . .
H15B H 0.971864 0.543462 0.167908 0.104 Uiso 1 1 calc R . . . .
O2A O 0.7602(12) 0.1386(8) 0.1409(9) 0.103(4) Uani 0.5 1 d . U P A -1
O1A O 0.4981(11) 0.2277(12) 0.1880(14) 0.082(4) Uani 0.5 1 d G U P A -1
H1A H 0.565495 0.275863 0.239440 0.123 Uiso 0.5 1 d R . P A -1
O3A O 0.520(3) -0.231(2) -0.187(2) 0.174(9) Uani 0.5 1 d . U P A -1
H3A H 0.436486 -0.283828 -0.225085 0.260 Uiso 0.5 1 calc GR . P A -1
C1A C 0.4694(12) 0.051(2) 0.0482(14) 0.064(4) Uani 0.5 1 d . U P A -1
C2A C 0.5496(14) -0.047(3) -0.0202(19) 0.085(5) Uani 0.5 1 d G U P A -1
H2A H 0.675933 -0.052259 -0.009199 0.102 Uiso 0.5 1 calc R . P A -1
C3A C 0.441(2) -0.138(2) -0.1050(15) 0.103(8) Uani 0.5 1 d G U P A -1
C4A C 0.2524(19) -0.1306(11) -0.1214(9) 0.126(9) Uani 0.5 1 d G U P A -1
H4A H 0.179841 -0.191356 -0.178121 0.152 Uiso 0.5 1 calc R . P A -1
C5A C 0.1721(11) -0.0323(8) -0.0530(7) 0.102(3) Uani 0.5 1 d G U P A -1
H5A H 0.045851 -0.027249 -0.064023 0.122 Uiso 0.5 1 calc R . P A -1
C6A C 0.2806(11) 0.0586(9) 0.0318(7) 0.086(2) Uani 0.5 1 d G U P A -1
H6A H 0.226900 0.124355 0.077488 0.103 Uiso 0.5 1 calc R . P A -1
C7A C 0.593(2) 0.1419(17) 0.1331(17) 0.071(4) Uani 0.5 1 d . U P A -1


_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 1.247(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.345(4) . ?
N1 C5 1.418(4) . ?
N2 C4 1.343(4) . ?
N2 C8 1.334(5) . ?
N3 C3 1.413(5) . ?
N3 C4 1.415(4) . ?
N3 C13 1.453(4) . ?
N4 C3 1.338(4) . ?
N4 C9 1.333(5) . ?
C1 C2 1.486(5) . ?
C2 C3 1.396(5) . ?
C2 C11 1.381(5) . ?
C4 C5 1.399(5) . ?
C5 C6 1.399(5) . ?
C6 C7 1.389(5) . ?
C6 C12 1.497(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.372(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(5) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9800 . ?
C13 C14 1.491(6) . ?
C13 C15 1.480(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.492(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O2A C7A 1.219(14) . ?
O1A H1A 0.8198 . ?
O1A C7A 1.294(14) . ?
O3A H3A 0.8200 . ?
O3A C3A 1.444(18) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C1A C7A 1.443(15) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C4A H4A 0.9300 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9300 . ?
C5A C6A 1.3900 . ?
C6A H6A 0.9300 . ?

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
C1 N1 H1 116.4 . . ?
C1 N1 C5 127.2(3) . . ?
C5 N1 H1 116.4 . . ?
C8 N2 C4 117.5(3) . . ?
C3 N3 C4 115.4(3) . . ?
C3 N3 C13 116.3(3) . . ?
C4 N3 C13 116.4(3) . . ?
C9 N4 C3 116.9(3) . . ?
O1 C1 N1 120.7(3) . . ?
O1 C1 C2 119.8(3) . . ?
N1 C1 C2 119.5(3) . . ?
C3 C2 C1 123.4(3) . . ?
C11 C2 C1 118.2(3) . . ?
C11 C2 C3 118.1(3) . . ?
N4 C3 N3 116.4(3) . . ?
N4 C3 C2 122.9(4) . . ?
C2 C3 N3 120.7(3) . . ?
N2 C4 N3 118.0(3) . . ?
N2 C4 C5 122.6(3) . . ?
C5 C4 N3 119.5(3) . . ?
C4 C5 N1 121.6(3) . . ?
C6 C5 N1 119.0(3) . . ?
C6 C5 C4 119.3(3) . . ?
C5 C6 C12 122.0(3) . . ?
C7 C6 C5 116.7(3) . . ?
C7 C6 C12 121.3(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.8 . . ?
N2 C8 C7 123.3(4) . . ?
N2 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
N4 C9 H9 117.3 . . ?
N4 C9 C10 125.3(4) . . ?
C10 C9 H9 117.3 . . ?
C9 C10 H10 121.6 . . ?
C9 C10 C11 116.9(4) . . ?
C11 C10 H10 121.6 . . ?
C2 C11 C10 119.7(4) . . ?
C2 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13 117.4 . . ?
N3 C13 C14 115.4(3) . . ?
N3 C13 C15 116.4(3) . . ?
C14 C13 H13 117.4 . . ?
C15 C13 H13 117.4 . . ?
C15 C13 C14 60.3(3) . . ?
C13 C14 H14A 117.8 . . ?
C13 C14 H14B 117.8 . . ?
C13 C14 C15 59.5(3) . . ?
H14A C14 H14B 115.0 . . ?
C15 C14 H14A 117.8 . . ?
C15 C14 H14B 117.8 . . ?
C13 C15 C14 60.2(3) . . ?
C13 C15 H15A 117.7 . . ?
C13 C15 H15B 117.7 . . ?
C14 C15 H15A 117.7 . . ?
C14 C15 H15B 117.7 . . ?
H15A C15 H15B 114.9 . . ?
C7A O1A H1A 109.1 . . ?
C3A O3A H3A 109.5 . . ?
C2A C1A C6A 120.0 . . ?
C2A C1A C7A 116.1(10) . . ?
C6A C1A C7A 123.9(10) . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A O3A 122.4(13) . . ?
C2A C3A C4A 120.0 . . ?
C4A C3A O3A 117.2(13) . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
O2A C7A O1A 129.1(14) . . ?
O2A C7A C1A 122.3(10) . . ?
O1A C7A C1A 108.4(14) . . ?

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 O1 0.86 2.10 2.950(4) 168.7 2_776 yes
O1A H1A N2 0.82 1.97 2.761(12) 161.8 . yes
O3A H3A N2 0.82 2.03 2.80(2) 156.8 2_655 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
O1 C1 C2 C3 139.7(4) . . . . ?
O1 C1 C2 C11 -33.9(5) . . . . ?
N1 C1 C2 C3 -41.3(5) . . . . ?
N1 C1 C2 C11 145.1(4) . . . . ?
N1 C5 C6 C7 -173.4(3) . . . . ?
N1 C5 C6 C12 6.7(5) . . . . ?
N2 C4 C5 N1 172.2(3) . . . . ?
N2 C4 C5 C6 -3.7(5) . . . . ?
N3 C4 C5 N1 -8.8(5) . . . . ?
N3 C4 C5 C6 175.2(3) . . . . ?
N3 C13 C14 C15 107.2(4) . . . . ?
N3 C13 C15 C14 -105.6(4) . . . . ?
N4 C9 C10 C11 4.4(7) . . . . ?
C1 N1 C5 C4 49.8(5) . . . . ?
C1 N1 C5 C6 -134.2(4) . . . . ?
C1 C2 C3 N3 8.7(5) . . . . ?
C1 C2 C3 N4 -169.4(3) . . . . ?
C1 C2 C11 C10 173.6(4) . . . . ?
C3 N3 C4 N2 118.1(3) . . . . ?
C3 N3 C4 C5 -60.9(4) . . . . ?
C3 N3 C13 C14 81.3(4) . . . . ?
C3 N3 C13 C15 149.2(4) . . . . ?
C3 N4 C9 C10 -0.8(6) . . . . ?
C3 C2 C11 C10 -0.4(6) . . . . ?
C4 N2 C8 C7 2.8(6) . . . . ?
C4 N3 C3 N4 -121.1(3) . . . . ?
C4 N3 C3 C2 60.7(4) . . . . ?
C4 N3 C13 C14 -137.6(4) . . . . ?
C4 N3 C13 C15 -69.8(4) . . . . ?
C4 C5 C6 C7 2.6(5) . . . . ?
C4 C5 C6 C12 -177.2(3) . . . . ?
C5 N1 C1 O1 172.4(3) . . . . ?
C5 N1 C1 C2 -6.5(6) . . . . ?
C5 C6 C7 C8 0.9(5) . . . . ?
C6 C7 C8 N2 -3.8(6) . . . . ?
C8 N2 C4 N3 -177.9(3) . . . . ?
C8 N2 C4 C5 1.0(5) . . . . ?
C9 N4 C3 N3 178.2(3) . . . . ?
C9 N4 C3 C2 -3.6(5) . . . . ?
C9 C10 C11 C2 -3.6(6) . . . . ?
C11 C2 C3 N3 -177.7(3) . . . . ?
C11 C2 C3 N4 4.2(6) . . . . ?
C12 C6 C7 C8 -179.3(4) . . . . ?
C13 N3 C3 N4 20.4(5) . . . . ?
C13 N3 C3 C2 -157.8(3) . . . . ?
C13 N3 C4 N2 -23.4(5) . . . . ?
C13 N3 C4 C5 157.6(3) . . . . ?
O3A C3A C4A C5A -173(2) . . . . ?
C1A C2A C3A O3A 173(2) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C2A C1A C7A O2A 3.9(17) . . . . ?
C2A C1A C7A O1A 179.2(10) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C6A C1A C7A O2A -175.4(18) . . . . ?
C6A C1A C7A O1A -0.1(16) . . . . ?
C7A C1A C2A C3A -179.3(13) . . . . ?
C7A C1A C6A C5A 179.3(14) . . . . ?

####################################################################### 
# 
# 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_gts
_database_code_depnum_ccdc_archive 'CCDC 2012055'
loop_
_audit_author_name
_audit_author_address
'Lourdes Infantes'
;CSIC
Spain
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N4 O, 0.5(C7 H6 O4)'
_chemical_formula_sum            'C18.50 H17 N4 O3'
_chemical_formula_weight         343.36
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1010(3)
_cell_length_b                   9.4938(4)
_cell_length_c                   12.0005(5)
_cell_angle_alpha                95.619(2)
_cell_angle_beta                 92.881(2)
_cell_angle_gamma                99.035(2)
_cell_volume                     793.37(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    120.04
_cell_measurement_theta_max      66.70
_cell_measurement_theta_min      5.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  0.752818
_exptl_absorpt_correction_T_min  0.616168
_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 39114 reflections, Rint = 0.0741
 (23184 with I > 3sig(I), Rint = 0.0608)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.097
_diffrn_reflns_Laue_measured_fraction_max 0.105
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2503
_diffrn_reflns_point_group_measured_fraction_full 0.097
_diffrn_reflns_point_group_measured_fraction_max 0.105
_diffrn_reflns_theta_full        66.821
_diffrn_reflns_theta_max         66.821
_diffrn_reflns_theta_min         4.744
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.097
_diffrn_measured_fraction_theta_max 0.105
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1681
_reflns_number_total             2503
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.1395
_refine_ls_R_factor_gt           0.0863
_refine_ls_restrained_S_all      1.064
_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)+(0.1045P)²+1.1123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2485
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.40(14)
 0.60(14)
2. 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 C(H,H,H) groups, All O(H) groups
3. Restrained distances
 O2A-C7A
 1.23 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C2A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C5A)
\\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of 0.001 and
sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 O1A, O2A, O3A, O4A, C1A, C2A, C3A, C4A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.01
6. Others
 Fixed Sof: O1A(0.5) H1A(0.5) O2A(0.5) O3A(0.5) H3A(0.5) O4A(0.5) H4A(0.5)
 C1A(0.5) C2A(0.5) C3A(0.5) H3AA(0.5) C4A(0.5) H4AA(0.5) C5A(0.5) C6A(0.5)
 H6A(0.5) C7A(0.5)
7.a Riding coordinates:
 O1A(H1A), O3A(H3A), O4A(H4A)
7.b Ternary CH refined with riding coordinates:
 C13(H13)
7.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
7.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C3A(H3AA), C4A(H4AA),
 C6A(H6A)
7.e Fitted hexagon refined as free rotating group:
 C1A(C2A,C3A,C4A,C5A,C6A)
7.f Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.193(10) -0.038(7) 0.577(6) 0.04(2) Uani 1 1 d . . . . .
N1 N 0.158(12) 0.187(9) 0.548(7) 0.04(2) Uani 1 1 d . . . . .
H1 H 0.045714 0.151957 0.513118 0.043 Uiso 1 1 calc R . . . .
N2 N 0.325(12) 0.568(9) 0.650(8) 0.04(2) Uani 1 1 d . . . . .
N3 N 0.317(12) 0.363(9) 0.747(7) 0.04(2) Uani 1 1 d . . . . .
N4 N 0.602(13) 0.302(10) 0.821(7) 0.04(2) Uani 1 1 d . . . . .
C1 C 0.251(14) 0.094(11) 0.594(9) 0.04(2) Uani 1 1 d . . . . .
C2 C 0.430(15) 0.148(11) 0.666(9) 0.04(3) Uani 1 1 d . . . . .
C3 C 0.454(15) 0.268(12) 0.744(9) 0.04(3) Uani 1 1 d . . . . .
C4 C 0.286(14) 0.425(11) 0.647(9) 0.04(2) Uani 1 1 d . . . . .
C5 C 0.220(14) 0.338(11) 0.547(9) 0.03(2) Uani 1 1 d . . . . .
C6 C 0.203(14) 0.399(11) 0.447(9) 0.04(2) Uani 1 1 d . . . . .
C7 C 0.243(14) 0.548(11) 0.453(9) 0.04(3) Uani 1 1 d . . . . .
H7 H 0.230501 0.594329 0.387101 0.047 Uiso 1 1 calc R . . . .
C8 C 0.300(15) 0.627(12) 0.555(10) 0.04(3) Uani 1 1 d . . . . .
H8 H 0.323176 0.728679 0.557438 0.051 Uiso 1 1 calc R . . . .
C9 C 0.735(16) 0.218(13) 0.817(10) 0.05(3) Uani 1 1 d . . . . .
H9 H 0.838697 0.240009 0.872218 0.054 Uiso 1 1 calc R . . . .
C10 C 0.735(16) 0.101(13) 0.739(10) 0.05(3) Uani 1 1 d . . . . .
H10 H 0.838255 0.048680 0.736748 0.058 Uiso 1 1 calc R . . . .
C11 C 0.574(15) 0.063(12) 0.663(9) 0.04(3) Uani 1 1 d . . . . .
H11 H 0.563375 -0.019551 0.610747 0.050 Uiso 1 1 calc R . . . .
C12 C 0.146(16) 0.308(12) 0.337(9) 0.04(3) Uani 1 1 d . . . . .
H12A H 0.014488 0.257038 0.338646 0.066 Uiso 1 1 calc GR . . . .
H12B H 0.232277 0.237432 0.325379 0.066 Uiso 1 1 calc GR . . . .
H12C H 0.152582 0.368618 0.275616 0.066 Uiso 1 1 calc GR . . . .
C13 C 0.320(16) 0.456(13) 0.850(9) 0.05(3) Uani 1 1 d . . . . .
H13 H 0.437554 0.529601 0.869387 0.057 Uiso 1 1 calc R . . . .
C14 C 0.222(17) 0.392(15) 0.944(10) 0.06(3) Uani 1 1 d . . . . .
H14A H 0.278204 0.424967 1.021379 0.067 Uiso 1 1 calc R . . . .
H14B H 0.161996 0.290082 0.931744 0.067 Uiso 1 1 calc R . . . .
C15 C 0.135(16) 0.497(13) 0.881(9) 0.05(3) Uani 1 1 d . . . . .
H15A H 0.020489 0.459818 0.829790 0.057 Uiso 1 1 calc R . . . .
H15B H 0.136672 0.594674 0.919406 0.057 Uiso 1 1 calc R . . . .
O1A O 0.49(2) 0.768(15) 0.818(12) 0.04(4) Uani 0.5 1 d . U P A -1
H1A H 0.429842 0.699284 0.775276 0.067 Uiso 0.5 1 d R . P A -1
O2A O 0.21(2) 0.835(17) 0.828(14) 0.05(4) Uani 0.5 1 d D U P A -1
O3A O 0.15(2) 1.038(17) 0.969(13) 0.05(4) Uani 0.5 1 d . U P A -1
H3A H 0.136981 0.991736 0.904880 0.073 Uiso 0.5 1 d R . P A -1
O4A O 0.90(2) 1.080(19) 1.131(14) 0.06(4) Uani 0.5 1 d . U P A -1
H4A H 0.973770 1.066350 1.079613 0.088 Uiso 0.5 1 d R . P A -1
C1A C 0.46(2) 0.957(18) 0.955(13) 0.04(3) Uani 0.5 1 d . U P A -1
C2A C 0.342(17) 1.046(17) 1.005(13) 0.04(3) Uani 0.5 1 d G U P A -1
C3A C 0.414(19) 1.145(16) 1.096(12) 0.04(3) Uani 0.5 1 d G U P A -1
H3AA H 0.335175 1.206488 1.129833 0.049 Uiso 0.5 1 calc R . P A -1
C4A C 0.60(2) 1.155(18) 1.136(13) 0.04(4) Uani 0.5 1 d G U P A -1
H4AA H 0.652934 1.222440 1.198552 0.050 Uiso 0.5 1 calc R . P A -1
C5A C 0.719(17) 1.065(17) 1.086(13) 0.04(3) Uani 0.5 1 d G U P A -1
C6A C 0.65(2) 0.966(16) 0.995(13) 0.04(3) Uani 0.5 1 d G U P A -1
H6A H 0.725439 0.904756 0.961211 0.049 Uiso 0.5 1 calc R . P A -1
C7A C 0.37(3) 0.85(3) 0.86(2) 0.04(5) Uani 0.5 1 d D U P A -1


_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 1.25(12) . ?
N1 H1 0.8800 . ?
N1 C1 1.33(13) . ?
N1 C5 1.43(13) . ?
N2 C4 1.34(13) . ?
N2 C8 1.34(14) . ?
N3 C3 1.42(13) . ?
N3 C4 1.41(13) . ?
N3 C13 1.44(13) . ?
N4 C3 1.34(14) . ?
N4 C9 1.33(14) . ?
C1 C2 1.49(15) . ?
C2 C3 1.39(15) . ?
C2 C11 1.40(14) . ?
C4 C5 1.40(15) . ?
C5 C6 1.39(14) . ?
C6 C7 1.39(14) . ?
C6 C12 1.51(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.38(16) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.38(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.40(15) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.49(17) . ?
C13 C15 1.49(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.50(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O1A H1A 0.8371 . ?
O1A C7A 1.3(3) . ?
O2A C7A 1.22(18) . ?
O3A H3A 0.8402 . ?
O3A C2A 1.37(18) . ?
O4A H4A 0.8455 . ?
O4A C5A 1.35(19) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900(19) . ?
C1A C7A 1.5(2) . ?
C2A C3A 1.3900(19) . ?
C3A H3AA 0.9500 . ?
C3A C4A 1.390(2) . ?
C4A H4AA 0.9500 . ?
C4A C5A 1.3900 . ?
C5A C6A 1.3900(17) . ?
C6A H6A 0.9500 . ?

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
C1 N1 H1 116.3 . . ?
C1 N1 C5 127(8) . . ?
C5 N1 H1 116.3 . . ?
C8 N2 C4 119(9) . . ?
C3 N3 C13 116(9) . . ?
C4 N3 C3 116(8) . . ?
C4 N3 C13 116(9) . . ?
C9 N4 C3 117(10) . . ?
O1 C1 N1 121(9) . . ?
O1 C1 C2 120(9) . . ?
N1 C1 C2 119(9) . . ?
C3 C2 C1 124(10) . . ?
C3 C2 C11 118(10) . . ?
C11 C2 C1 118(10) . . ?
N4 C3 N3 116(10) . . ?
N4 C3 C2 123(10) . . ?
C2 C3 N3 120(9) . . ?
N2 C4 N3 118(9) . . ?
N2 C4 C5 121(10) . . ?
C5 C4 N3 120(9) . . ?
C4 C5 N1 121(9) . . ?
C6 C5 N1 119(9) . . ?
C6 C5 C4 120(9) . . ?
C5 C6 C12 121(9) . . ?
C7 C6 C5 117(10) . . ?
C7 C6 C12 122(10) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 120(10) . . ?
C8 C7 H7 120.1 . . ?
N2 C8 C7 123(10) . . ?
N2 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
N4 C9 H9 117.3 . . ?
N4 C9 C10 125(10) . . ?
C10 C9 H9 117.3 . . ?
C9 C10 H10 121.7 . . ?
C9 C10 C11 117(10) . . ?
C11 C10 H10 121.7 . . ?
C2 C11 H11 120.2 . . ?
C10 C11 C2 120(10) . . ?
C10 C11 H11 120.2 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13 117.0 . . ?
N3 C13 C14 116(10) . . ?
N3 C13 C15 117(9) . . ?
C14 C13 H13 117.0 . . ?
C15 C13 H13 117.0 . . ?
C15 C13 C14 60(8) . . ?
C13 C14 H14A 117.8 . . ?
C13 C14 H14B 117.8 . . ?
C13 C14 C15 60(8) . . ?
H14A C14 H14B 114.9 . . ?
C15 C14 H14A 117.8 . . ?
C15 C14 H14B 117.8 . . ?
C13 C15 C14 60(8) . . ?
C13 C15 H15A 117.8 . . ?
C13 C15 H15B 117.8 . . ?
C14 C15 H15A 117.8 . . ?
C14 C15 H15B 117.8 . . ?
H15A C15 H15B 114.9 . . ?
C7A O1A H1A 110.1 . . ?
C2A O3A H3A 107.3 . . ?
C5A O4A H4A 109.0 . . ?
C2A C1A C6A 120.00(11) . . ?
C2A C1A C7A 119(10) . . ?
C6A C1A C7A 121(10) . . ?
C1A C2A O3A 122(10) . . ?
C1A C2A C3A 120.00(14) . . ?
C3A C2A O3A 118(10) . . ?
C2A C3A H3AA 120.0 . . ?
C2A C3A C4A 120.00(9) . . ?
C4A C3A H3AA 120.0 . . ?
C3A C4A H4AA 120.0 . . ?
C5A C4A C3A 120.00(15) . . ?
C5A C4A H4AA 120.0 . . ?
O4A C5A C4A 116(10) . . ?
O4A C5A C6A 124(10) . . ?
C4A C5A C6A 120.00(16) . . ?
C1A C6A H6A 120.0 . . ?
C5A C6A C1A 120.00(7) . . ?
C5A C6A H6A 120.0 . . ?
O1A C7A C1A 115(10) . . ?
O2A C7A O1A 123(10) . . ?
O2A C7A C1A 122(10) . . ?

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
O1A H1A N2 0.84 1.90 2.72(16) 164.9 . yes
O3A H3A O2A 0.84 1.82 2.5(2) 140.6 . 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
O1 C1 C2 C3 -139(11) . . . . ?
O1 C1 C2 C11 33(14) . . . . ?
N1 C1 C2 C3 42(15) . . . . ?
N1 C1 C2 C11 -146(10) . . . . ?
N1 C5 C6 C7 172(9) . . . . ?
N1 C5 C6 C12 -8(14) . . . . ?
N2 C4 C5 N1 -173(9) . . . . ?
N2 C4 C5 C6 3(15) . . . . ?
N3 C4 C5 N1 9(14) . . . . ?
N3 C4 C5 C6 -175(9) . . . . ?
N3 C13 C14 C15 -107(11) . . . . ?
N3 C13 C15 C14 107(12) . . . . ?
N4 C9 C10 C11 -4(17) . . . . ?
C1 N1 C5 C4 -50(15) . . . . ?
C1 N1 C5 C6 133(11) . . . . ?
C1 C2 C3 N3 -12(16) . . . . ?
C1 C2 C3 N4 168(10) . . . . ?
C1 C2 C11 C10 -172(10) . . . . ?
C3 N3 C4 N2 -118(10) . . . . ?
C3 N3 C4 C5 60(12) . . . . ?
C3 N3 C13 C14 -80(12) . . . . ?
C3 N3 C13 C15 -149(10) . . . . ?
C3 N4 C9 C10 1(16) . . . . ?
C3 C2 C11 C10 0(15) . . . . ?
C4 N2 C8 C7 -3(15) . . . . ?
C4 N3 C3 N4 122(10) . . . . ?
C4 N3 C3 C2 -58(13) . . . . ?
C4 N3 C13 C14 139(10) . . . . ?
C4 N3 C13 C15 71(13) . . . . ?
C4 C5 C6 C7 -4(14) . . . . ?
C4 C5 C6 C12 176(9) . . . . ?
C5 N1 C1 O1 -171(10) . . . . ?
C5 N1 C1 C2 8(16) . . . . ?
C5 C6 C7 C8 2(15) . . . . ?
C6 C7 C8 N2 2(16) . . . . ?
C8 N2 C4 N3 178(9) . . . . ?
C8 N2 C4 C5 0(14) . . . . ?
C9 N4 C3 N3 -177(9) . . . . ?
C9 N4 C3 C2 3(15) . . . . ?
C9 C10 C11 C2 4(16) . . . . ?
C11 C2 C3 N3 177(9) . . . . ?
C11 C2 C3 N4 -4(16) . . . . ?
C12 C6 C7 C8 -178(9) . . . . ?
C13 N3 C3 N4 -18(13) . . . . ?
C13 N3 C3 C2 162(10) . . . . ?
C13 N3 C4 N2 22(13) . . . . ?
C13 N3 C4 C5 -160(9) . . . . ?
O3A C2A C3A C4A 179(15) . . . . ?
O4A C5A C6A C1A 179(17) . . . . ?
C1A C2A C3A C4A 0.00(7) . . . . ?
C2A C1A C6A C5A 0.00(6) . . . . ?
C2A C1A C7A O1A -179(14) . . . . ?
C2A C1A C7A O2A -4(36) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A O4A -180(16) . . . . ?
C3A C4A C5A C6A 0.00(7) . . . . ?
C4A C5A C6A C1A 0.00(6) . . . . ?
C6A C1A C2A O3A -178(15) . . . . ?
C6A C1A C2A C3A 0.00(7) . . . . ?
C6A C1A C7A O1A 0(32) . . . . ?
C6A C1A C7A O2A 175(17) . . . . ?
C7A C1A C2A O3A 0(21) . . . . ?
C7A C1A C2A C3A 179(23) . . . . ?
C7A C1A C6A C5A -179(24) . . . . ?

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.40(14)
2 0.60(14)

