# 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. 
# 
#######################################################################

data_lik1_a
_database_code_depnum_ccdc_archive 'CCDC 1963600'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_vrf_PLAT029_lik1_a              
;
PROBLEM: Diffrn_measured_fraction_theta_full value Low . 0.946 Why?
RESPONSE: The quality of the crystals were not good. We tried several times for better completeness, but we could not obtain higher than 0.946.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H23 N3 O2'
_chemical_formula_sum            'C16 H23 N3 O2'
_chemical_formula_weight         289.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3955(5)
_cell_length_b                   9.6559(7)
_cell_length_c                   22.6536(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.448(2)
_cell_angle_gamma                90
_cell_volume                     1607.47(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3803
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.90

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13917
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.779
_diffrn_reflns_theta_max         27.130
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             3376
_reflns_number_gt                2534
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0744P)²+1.0354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3376
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57226(19) 0.51754(13) 0.57020(6) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.4981(2) 0.72473(15) 0.67949(6) 0.0350(4) Uani 1 1 d . . . . .
N1 N 0.2877(2) 0.73353(15) 0.48085(6) 0.0184(3) Uani 1 1 d . . . . .
H1N H 0.322141 0.645356 0.475673 0.022 Uiso 1 1 d R U . . .
N2 N 0.3364(2) 0.79544(15) 0.53305(6) 0.0171(3) Uani 1 1 d . . . . .
N3 N 0.2781(2) 0.48724(15) 0.58771(7) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.2101(3) 0.81453(17) 0.43294(7) 0.0165(4) Uani 1 1 d . . . . .
C2 C 0.1469(3) 0.94750(18) 0.44171(8) 0.0200(4) Uani 1 1 d . . . . .
H2A H 0.159365 0.987101 0.480345 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0652(3) 1.02203(18) 0.39352(8) 0.0221(4) Uani 1 1 d . . . . .
H3A H 0.023969 1.113524 0.399661 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0421(3) 0.96664(18) 0.33647(8) 0.0199(4) Uani 1 1 d . . . . .
C5 C 0.1055(3) 0.83280(19) 0.32886(8) 0.0206(4) Uani 1 1 d . . . . .
H5A H 0.091121 0.792524 0.290355 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1890(3) 0.75706(18) 0.37623(7) 0.0188(4) Uani 1 1 d . . . . .
H6A H 0.231871 0.666048 0.370016 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3969(3) 0.72093(17) 0.57847(7) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.4526(3) 0.79349(18) 0.63515(8) 0.0210(4) Uani 1 1 d . . . . .
C9 C 0.4490(3) 0.94881(19) 0.63627(9) 0.0254(4) Uani 1 1 d . . . . .
H9A H 0.408865 0.983829 0.596344 0.038 Uiso 1 1 calc R U . . .
H9B H 0.364568 0.980167 0.663869 0.038 Uiso 1 1 calc R U . . .
H9C H 0.571339 0.983896 0.649340 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4225(3) 0.56502(18) 0.57831(7) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.0975(3) 0.5435(2) 0.59372(9) 0.0269(5) Uani 1 1 d . . . . .
H11A H 0.004721 0.482488 0.572165 0.032 Uiso 1 1 calc R U . . .
H11B H 0.086789 0.635821 0.574672 0.032 Uiso 1 1 calc R U . . .
C12 C 0.0570(3) 0.5572(2) 0.65771(10) 0.0358(5) Uani 1 1 d . . . . .
H12A H -0.065496 0.595252 0.658566 0.054 Uiso 1 1 calc R U . . .
H12B H 0.064145 0.465821 0.676673 0.054 Uiso 1 1 calc R U . . .
H12C H 0.146295 0.619308 0.679182 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2982(3) 0.33593(18) 0.59056(8) 0.0242(4) Uani 1 1 d . . . . .
H13A H 0.221815 0.298746 0.620081 0.029 Uiso 1 1 calc R U . . .
H13B H 0.426507 0.312739 0.604218 0.029 Uiso 1 1 calc R U . . .
C14 C 0.2439(3) 0.2672(2) 0.53106(9) 0.0300(5) Uani 1 1 d . . . . .
H14A H 0.259589 0.166696 0.535133 0.045 Uiso 1 1 calc R U . . .
H14B H 0.116228 0.288153 0.517726 0.045 Uiso 1 1 calc R U . . .
H14C H 0.320916 0.302146 0.501863 0.045 Uiso 1 1 calc R U . . .
C15 C -0.0460(3) 1.0483(2) 0.28415(8) 0.0272(5) Uani 1 1 d . . . . .
H15A H -0.122738 1.121966 0.298749 0.033 Uiso 1 1 calc R U . . .
H15B H -0.126259 0.986079 0.258222 0.033 Uiso 1 1 calc R U . . .
C16 C 0.0916(4) 1.1137(3) 0.24794(10) 0.0420(6) Uani 1 1 d . . . . .
H16A H 0.027653 1.165319 0.214651 0.063 Uiso 1 1 calc R U . . .
H16B H 0.169838 1.177060 0.273137 0.063 Uiso 1 1 calc R U . . .
H16C H 0.166315 1.041139 0.232601 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.231(2) . ?
O2 C8 1.220(2) . ?
N1 N2 1.3377(19) . ?
N1 C1 1.407(2) . ?
N1 H1N 0.9001 . ?
N2 C7 1.294(2) . ?
N3 C10 1.342(2) . ?
N3 C11 1.462(3) . ?
N3 C13 1.469(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.388(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(3) . ?
C4 C15 1.509(3) . ?
C5 C6 1.385(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.480(2) . ?
C7 C10 1.517(2) . ?
C8 C9 1.500(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.516(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.515(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 118.65(14) . . ?
N2 N1 H1N 119.1 . . ?
C1 N1 H1N 121.5 . . ?
C7 N2 N1 119.29(14) . . ?
C10 N3 C11 123.97(15) . . ?
C10 N3 C13 118.99(16) . . ?
C11 N3 C13 117.02(15) . . ?
C2 C1 C6 119.75(16) . . ?
C2 C1 N1 121.23(15) . . ?
C6 C1 N1 118.95(15) . . ?
C3 C2 C1 119.38(16) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 121.91(16) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 C5 117.64(17) . . ?
C3 C4 C15 121.73(16) . . ?
C5 C4 C15 120.63(16) . . ?
C6 C5 C4 121.42(16) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C1 119.89(16) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
N2 C7 C8 117.68(15) . . ?
N2 C7 C10 125.60(15) . . ?
C8 C7 C10 116.68(15) . . ?
O2 C8 C7 118.76(16) . . ?
O2 C8 C9 122.27(17) . . ?
C7 C8 C9 118.96(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 N3 124.10(17) . . ?
O1 C10 C7 118.99(17) . . ?
N3 C10 C7 116.91(17) . . ?
N3 C11 C12 113.65(17) . . ?
N3 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N3 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 112.40(16) . . ?
N3 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 C16 112.73(19) . . ?
C4 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C4 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C1 N1 N2 C7 175.53(16) . . . . ?
N2 N1 C1 C2 -14.4(3) . . . . ?
N2 N1 C1 C6 168.67(16) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
N1 C1 C2 C3 -177.68(18) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 C15 -179.73(18) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C15 C4 C5 C6 179.07(18) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C5 177.10(17) . . . . ?
N1 N2 C7 C8 178.88(16) . . . . ?
N1 N2 C7 C10 1.3(3) . . . . ?
N2 C7 C8 O2 175.00(19) . . . . ?
C10 C7 C8 O2 -7.2(3) . . . . ?
N2 C7 C8 C9 -4.3(3) . . . . ?
C10 C7 C8 C9 173.55(18) . . . . ?
C11 N3 C10 O1 -176.11(17) . . . . ?
C13 N3 C10 O1 2.0(3) . . . . ?
C11 N3 C10 C7 4.5(2) . . . . ?
C13 N3 C10 C7 -177.36(15) . . . . ?
N2 C7 C10 O1 93.5(2) . . . . ?
C8 C7 C10 O1 -84.2(2) . . . . ?
N2 C7 C10 N3 -87.1(2) . . . . ?
C8 C7 C10 N3 95.3(2) . . . . ?
C10 N3 C11 C12 -99.4(2) . . . . ?
C13 N3 C11 C12 82.4(2) . . . . ?
C10 N3 C13 C14 -93.9(2) . . . . ?
C11 N3 C13 C14 84.3(2) . . . . ?
C3 C4 C15 C16 98.8(2) . . . . ?
C5 C4 C15 C16 -80.4(2) . . . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_LIK4
_database_code_depnum_ccdc_archive 'CCDC 1963601'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N3 O2'
_chemical_formula_sum            'C14 H19 N3 O2'
_chemical_formula_weight         261.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4907(6)
_cell_length_b                   9.7684(8)
_cell_length_c                   10.3754(10)
_cell_angle_alpha                88.424(3)
_cell_angle_beta                 75.466(3)
_cell_angle_gamma                86.310(3)
_cell_volume                     733.32(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4672
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.67

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10401
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.895
_diffrn_reflns_theta_max         25.691
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2745
_reflns_number_gt                2128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²+0.1064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2745
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38268(15) 0.48470(10) 0.65307(11) 0.0651(3) Uani 1 1 d . . . . .
N1 N 0.70585(16) 0.25742(11) 0.47868(11) 0.0493(3) Uani 1 1 d . . . . .
H1N H 0.675993 0.344232 0.457014 0.059 Uiso 1 1 d R U . . .
C1 C 0.81022(18) 0.17279(14) 0.37625(13) 0.0459(3) Uani 1 1 d . . . . .
N2 N 0.62107(15) 0.19827(11) 0.59324(10) 0.0442(3) Uani 1 1 d . . . . .
O2 O 0.3520(2) 0.26572(15) 0.90929(13) 0.1045(6) Uani 1 1 d . . . . .
C2 C 0.8435(2) 0.03501(16) 0.39770(15) 0.0652(4) Uani 1 1 d . . . . .
H2A H 0.793616 -0.004439 0.480470 0.078 Uiso 1 1 calc R U . . .
N3 N 0.63988(17) 0.49393(12) 0.72927(13) 0.0578(3) Uani 1 1 d . . . . .
C3 C 0.9511(3) -0.0445(2) 0.29606(19) 0.0840(6) Uani 1 1 d . . . . .
H3A H 0.971991 -0.137836 0.310855 0.101 Uiso 1 1 calc R U . . .
C4 C 1.0273(2) 0.0111(2) 0.17458(18) 0.0802(6) Uani 1 1 d . . . . .
H4A H 1.099852 -0.043566 0.106927 0.096 Uiso 1 1 calc R U . . .
C5 C 0.9958(2) 0.1489(2) 0.15297(16) 0.0721(5) Uani 1 1 d . . . . .
H5A H 1.048530 0.187792 0.070439 0.087 Uiso 1 1 calc R U . . .
C6 C 0.8866(2) 0.23035(17) 0.25269(14) 0.0581(4) Uani 1 1 d . . . . .
H6A H 0.864537 0.323322 0.236986 0.070 Uiso 1 1 calc R U . . .
C7 C 0.53262(18) 0.27275(13) 0.69237(13) 0.0458(3) Uani 1 1 d . . . . .
C8 C 0.4406(2) 0.19990(16) 0.81498(14) 0.0589(4) Uani 1 1 d . . . . .
C9 C 0.4624(2) 0.04675(17) 0.81975(17) 0.0687(5) Uani 1 1 d . . . . .
H9A H 0.383640 0.013392 0.900782 0.103 Uiso 1 1 calc R U . . .
H9B H 0.588609 0.018785 0.816619 0.103 Uiso 1 1 calc R U . . .
H9C H 0.428830 0.009740 0.744928 0.103 Uiso 1 1 calc R U . . .
C10 C 0.51259(19) 0.42726(13) 0.69045(13) 0.0482(3) Uani 1 1 d . . . . .
C11 C 0.6273(3) 0.64408(15) 0.72984(19) 0.0714(5) Uani 1 1 d . . . . .
H11A H 0.673461 0.675370 0.802645 0.086 Uiso 1 1 calc R U . . .
H11B H 0.498627 0.676471 0.745304 0.086 Uiso 1 1 calc R U . . .
C12 C 0.7347(3) 0.7051(2) 0.6018(2) 0.0969(7) Uani 1 1 d . . . . .
H12A H 0.726608 0.803255 0.608404 0.145 Uiso 1 1 calc R U . . .
H12B H 0.684411 0.679297 0.530144 0.145 Uiso 1 1 calc R U . . .
H12C H 0.861703 0.671838 0.585002 0.145 Uiso 1 1 calc R U . . .
C13 C 0.8018(3) 0.42602(19) 0.7635(2) 0.0823(6) Uani 1 1 d . . . . .
H13A H 0.909879 0.474904 0.720175 0.099 Uiso 1 1 calc R U . . .
H13B H 0.819637 0.333616 0.728702 0.099 Uiso 1 1 calc R U . . .
C14 C 0.7880(5) 0.4186(3) 0.9084(3) 0.1331(11) Uani 1 1 d . . . . .
H14A H 0.902901 0.381264 0.923304 0.200 Uiso 1 1 calc R U . . .
H14B H 0.690715 0.360845 0.950777 0.200 Uiso 1 1 calc R U . . .
H14C H 0.761397 0.509044 0.944992 0.200 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.2327(16) . ?
N1 N2 1.3343(15) . ?
N1 C1 1.4044(16) . ?
N1 H1N 0.9000 . ?
C1 C2 1.375(2) . ?
C1 C6 1.386(2) . ?
N2 C7 1.2896(16) . ?
O2 C8 1.2106(19) . ?
C2 C3 1.380(2) . ?
C2 H2A 0.9300 . ?
N3 C10 1.3352(18) . ?
N3 C13 1.462(2) . ?
N3 C11 1.4638(18) . ?
C3 C4 1.360(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.4740(19) . ?
C7 C10 1.5072(18) . ?
C8 C9 1.495(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.499(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.481(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 118.18(11) . . ?
N2 N1 H1N 122.3 . . ?
C1 N1 H1N 117.6 . . ?
C2 C1 C6 119.45(13) . . ?
C2 C1 N1 121.24(13) . . ?
C6 C1 N1 119.27(13) . . ?
C7 N2 N1 120.13(11) . . ?
C1 C2 C3 119.80(16) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C10 N3 C13 123.74(13) . . ?
C10 N3 C11 119.49(13) . . ?
C13 N3 C11 116.63(13) . . ?
C4 C3 C2 121.19(18) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 119.25(15) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C6 120.62(16) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 119.68(16) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
N2 C7 C8 116.94(12) . . ?
N2 C7 C10 124.91(12) . . ?
C8 C7 C10 118.13(11) . . ?
O2 C8 C7 119.14(14) . . ?
O2 C8 C9 121.98(14) . . ?
C7 C8 C9 118.88(13) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 N3 123.86(13) . . ?
O1 C10 C7 119.11(12) . . ?
N3 C10 C7 117.03(12) . . ?
N3 C11 C12 112.56(16) . . ?
N3 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 113.85(19) . . ?
N3 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N3 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N2 N1 C1 C2 -7.8(2) . . . . ?
N2 N1 C1 C6 174.59(11) . . . . ?
C1 N1 N2 C7 176.05(11) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
N1 C1 C2 C3 -178.08(15) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
N1 C1 C6 C5 177.34(13) . . . . ?
N1 N2 C7 C8 179.26(11) . . . . ?
N1 N2 C7 C10 1.0(2) . . . . ?
N2 C7 C8 O2 -178.08(15) . . . . ?
C10 C7 C8 O2 0.3(2) . . . . ?
N2 C7 C8 C9 2.9(2) . . . . ?
C10 C7 C8 C9 -178.68(13) . . . . ?
C13 N3 C10 O1 -174.97(15) . . . . ?
C11 N3 C10 O1 0.6(2) . . . . ?
C13 N3 C10 C7 4.6(2) . . . . ?
C11 N3 C10 C7 -179.83(13) . . . . ?
N2 C7 C10 O1 88.16(18) . . . . ?
C8 C7 C10 O1 -90.09(16) . . . . ?
N2 C7 C10 N3 -91.40(17) . . . . ?
C8 C7 C10 N3 90.34(16) . . . . ?
C10 N3 C11 C12 -92.09(19) . . . . ?
C13 N3 C11 C12 83.8(2) . . . . ?
C10 N3 C13 C14 -104.7(2) . . . . ?
C11 N3 C13 C14 79.5(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
N1 H1N O1 0.90 2.08 2.9504(15) 161.3 2_666 yes

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_LIK3
_database_code_depnum_ccdc_archive 'CCDC 1963602'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-12-10 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N3 O4.08'
_chemical_formula_sum            'C15 H19 N3 O4.08'
_chemical_formula_weight         306.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5227(3)
_cell_length_b                   15.5942(6)
_cell_length_c                   13.0925(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.426(2)
_cell_angle_gamma                90
_cell_volume                     1531.31(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5545
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.91

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             650
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13476
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.716
_diffrn_reflns_theta_max         27.960
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3662
_reflns_number_gt                2981
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0853P)²+0.4758P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3662
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.98660(16) 0.33735(7) -0.20308(8) 0.0469(3) Uani 1 1 d . . . . .
O2 O 0.73005(14) 0.21927(6) -0.05723(7) 0.0362(2) Uani 1 1 d . . . . .
O3 O 0.40786(15) 0.71188(6) 0.32811(8) 0.0382(3) Uani 1 1 d . . . . .
O4 O 0.43321(17) 0.61103(7) 0.44867(8) 0.0457(3) Uani 1 1 d . . . . .
H4O H 0.387(3) 0.6521(16) 0.4844(18) 0.071(7) Uiso 1 1 d . . . . .
O5 O 0.6717(18) 0.3510(6) 0.2994(8) 0.031(4) Uani 0.079(4) 1 d . . P A 1
H5 H 0.777145 0.356048 0.324821 0.046 Uiso 0.079(4) 1 calc R U P A 1
N1 N 0.71227(14) 0.38821(7) 0.09249(8) 0.0266(2) Uani 1 1 d . . . . .
H1N H 0.712544 0.332868 0.112034 0.032 Uiso 1 1 d R U . . .
N2 N 0.77804(13) 0.41309(7) 0.00544(8) 0.0249(2) Uani 1 1 d . . . . .
N3 N 1.01451(16) 0.23230(7) 0.01373(9) 0.0311(3) Uani 1 1 d . . . . .
C1 C 0.64717(15) 0.45114(8) 0.15622(9) 0.0242(2) Uani 1 1 d . . . . .
C2 C 0.61845(16) 0.53531(8) 0.12201(9) 0.0262(3) Uani 1 1 d . . . . .
H2A H 0.640862 0.550645 0.053965 0.031 Uiso 1 1 calc R U . . .
C3 C 0.55713(16) 0.59623(8) 0.18785(10) 0.0269(3) Uani 1 1 d . . . . .
H3A H 0.537465 0.653431 0.164680 0.032 Uiso 1 1 calc R U . . .
C4 C 0.52422(15) 0.57431(8) 0.28744(9) 0.0256(3) Uani 1 1 d . . . . .
C5 C 0.55400(17) 0.49010(8) 0.32108(9) 0.0286(3) Uani 1 1 d . . . . .
H5A H 0.532396 0.474966 0.389312 0.034 Uiso 1 1 calc R U . . .
C6 C 0.61463(16) 0.42851(8) 0.25602(9) 0.0279(3) Uani 1 1 d . . . . .
H6A H 0.633902 0.371295 0.279218 0.033 Uiso 0.921(4) 1 calc R U P A 2
C7 C 0.85216(16) 0.35798(8) -0.05129(9) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.91837(17) 0.38869(8) -0.14853(9) 0.0293(3) Uani 1 1 d . . . . .
C9 C 0.89998(19) 0.48143(9) -0.17449(11) 0.0341(3) Uani 1 1 d . . . . .
H9A H 0.951189 0.492428 -0.239828 0.051 Uiso 1 1 calc R U . . .
H9B H 0.963172 0.515699 -0.120446 0.051 Uiso 1 1 calc R U . . .
H9C H 0.773484 0.497165 -0.180287 0.051 Uiso 1 1 calc R U . . .
C10 C 0.86351(17) 0.26306(8) -0.03079(9) 0.0268(3) Uani 1 1 d . . . . .
C11 C 1.16954(18) 0.28593(9) 0.04556(12) 0.0367(3) Uani 1 1 d . . . . .
H11A H 1.157077 0.342195 0.010723 0.044 Uiso 1 1 calc R U . . .
H11B H 1.278890 0.258159 0.023964 0.044 Uiso 1 1 calc R U . . .
C12 C 1.1886(2) 0.29980(10) 0.16010(13) 0.0432(4) Uani 1 1 d . . . . .
H12A H 1.293662 0.335429 0.178144 0.065 Uiso 1 1 calc R U . . .
H12B H 1.202559 0.244285 0.194886 0.065 Uiso 1 1 calc R U . . .
H12C H 1.081934 0.328671 0.181571 0.065 Uiso 1 1 calc R U . . .
C13 C 1.0378(2) 0.13946(9) 0.02836(12) 0.0397(3) Uani 1 1 d . . . . .
H13A H 0.922159 0.113204 0.041976 0.048 Uiso 1 1 calc R U . . .
H13B H 1.122870 0.128739 0.088521 0.048 Uiso 1 1 calc R U . . .
C14 C 1.1068(3) 0.09855(11) -0.06530(16) 0.0569(5) Uani 1 1 d . . . . .
H14A H 1.133649 0.038005 -0.051222 0.085 Uiso 1 1 calc R U . . .
H14B H 1.215398 0.128139 -0.082558 0.085 Uiso 1 1 calc R U . . .
H14C H 1.016022 0.102928 -0.122925 0.085 Uiso 1 1 calc R U . . .
C15 C 0.44998(16) 0.63974(8) 0.35508(9) 0.0275(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
O1 C8 1.2130(17) . ?
O2 C10 1.2411(16) . ?
O3 C15 1.2139(16) . ?
O4 C15 1.3198(16) . ?
O4 H4O 0.88(2) . ?
O5 C6 1.389(10) . ?
O5 H5 0.8400 . ?
N1 N2 1.3347(14) . ?
N1 C1 1.4008(15) . ?
N1 H1N 0.9001 . ?
N2 C7 1.2904(16) . ?
N3 C10 1.3258(17) . ?
N3 C13 1.4692(17) . ?
N3 C11 1.4691(18) . ?
C1 C6 1.3932(17) . ?
C1 C2 1.3983(17) . ?
C2 C3 1.3855(17) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3887(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3977(18) . ?
C4 C15 1.4877(17) . ?
C5 C6 1.3842(18) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.4819(16) . ?
C7 C10 1.5056(17) . ?
C8 C9 1.4895(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.511(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.509(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C15 O4 H4O 108.5(15) . . ?
C6 O5 H5 109.5 . . ?
N2 N1 C1 118.34(10) . . ?
N2 N1 H1N 121.9 . . ?
C1 N1 H1N 119.7 . . ?
C7 N2 N1 120.20(10) . . ?
C10 N3 C13 120.22(12) . . ?
C10 N3 C11 123.59(11) . . ?
C13 N3 C11 116.10(12) . . ?
C6 C1 C2 120.28(11) . . ?
C6 C1 N1 118.42(11) . . ?
C2 C1 N1 121.29(11) . . ?
C3 C2 C1 119.67(11) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 120.49(12) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 119.43(11) . . ?
C3 C4 C15 119.49(11) . . ?
C5 C4 C15 121.01(11) . . ?
C6 C5 C4 120.69(11) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 O5 117.3(4) . . ?
C5 C6 C1 119.44(12) . . ?
O5 C6 C1 122.2(4) . . ?
C5 C6 H6A 120.3 . . ?
C1 C6 H6A 120.3 . . ?
N2 C7 C8 117.90(11) . . ?
N2 C7 C10 124.98(11) . . ?
C8 C7 C10 116.92(10) . . ?
O1 C8 C7 118.56(12) . . ?
O1 C8 C9 122.86(12) . . ?
C7 C8 C9 118.58(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N3 124.80(12) . . ?
O2 C10 C7 117.23(12) . . ?
N3 C10 C7 117.96(11) . . ?
N3 C11 C12 112.06(12) . . ?
N3 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 110.83(12) . . ?
N3 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 122.88(12) . . ?
O3 C15 C4 124.34(12) . . ?
O4 C15 C4 112.78(11) . . ?

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
C1 N1 N2 C7 174.47(11) . . . . ?
N2 N1 C1 C6 -166.32(11) . . . . ?
N2 N1 C1 C2 12.39(17) . . . . ?
C6 C1 C2 C3 -0.09(18) . . . . ?
N1 C1 C2 C3 -178.78(11) . . . . ?
C1 C2 C3 C4 0.06(18) . . . . ?
C2 C3 C4 C5 0.20(18) . . . . ?
C2 C3 C4 C15 -177.00(11) . . . . ?
C3 C4 C5 C6 -0.43(18) . . . . ?
C15 C4 C5 C6 176.73(11) . . . . ?
C4 C5 C6 O5 168.6(6) . . . . ?
C4 C5 C6 C1 0.39(19) . . . . ?
C2 C1 C6 C5 -0.14(18) . . . . ?
N1 C1 C6 C5 178.59(11) . . . . ?
C2 C1 C6 O5 -167.8(7) . . . . ?
N1 C1 C6 O5 11.0(7) . . . . ?
N1 N2 C7 C8 178.33(10) . . . . ?
N1 N2 C7 C10 3.63(18) . . . . ?
N2 C7 C8 O1 -179.22(12) . . . . ?
C10 C7 C8 O1 -4.08(18) . . . . ?
N2 C7 C8 C9 1.42(17) . . . . ?
C10 C7 C8 C9 176.55(12) . . . . ?
C13 N3 C10 O2 4.53(19) . . . . ?
C11 N3 C10 O2 -179.07(12) . . . . ?
C13 N3 C10 C7 -175.31(11) . . . . ?
C11 N3 C10 C7 1.09(18) . . . . ?
N2 C7 C10 O2 81.19(16) . . . . ?
C8 C7 C10 O2 -93.57(13) . . . . ?
N2 C7 C10 N3 -98.96(15) . . . . ?
C8 C7 C10 N3 86.28(14) . . . . ?
C10 N3 C11 C12 104.19(14) . . . . ?
C13 N3 C11 C12 -79.28(15) . . . . ?
C10 N3 C13 C14 86.69(17) . . . . ?
C11 N3 C13 C14 -89.97(17) . . . . ?
C3 C4 C15 O3 3.22(19) . . . . ?
C5 C4 C15 O3 -173.94(13) . . . . ?
C3 C4 C15 O4 -177.14(11) . . . . ?
C5 C4 C15 O4 5.71(17) . . . . ?

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
O4 H4O O2 0.88(2) 1.71(2) 2.5782(14) 170(2) 2_655 yes
N1 H1N O3 0.90 2.26 3.0988(14) 155.1 2_645 yes
C9 H9B N2 0.98 2.61 3.5558(18) 161.0 3_765 yes
C12 H12B O1 0.98 2.53 3.242(2) 129.8 4_566 yes

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_lik2
_database_code_depnum_ccdc_archive 'CCDC 1963603'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N4 O2'
_chemical_formula_sum            'C15 H18 N4 O2'
_chemical_formula_weight         286.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.6003(4)
_cell_length_b                   19.5864(12)
_cell_length_c                   10.5405(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.758(2)
_cell_angle_gamma                90
_cell_volume                     1565.71(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      25.62

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24894
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.198
_diffrn_reflns_theta_max         25.724
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5928
_reflns_number_gt                4939
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+0.0871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5928
_refine_ls_number_parameters     385
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2064(3) 0.43179(11) 0.63567(18) 0.0661(5) Uani 1 1 d . . . . .
N1 N 0.4679(3) 0.48908(11) 0.4278(2) 0.0516(5) Uani 1 1 d . . . . .
H1N H 0.438873 0.508283 0.501172 0.062 Uiso 1 1 d R U . . .
C1 C 0.5081(3) 0.53123(13) 0.3274(2) 0.0473(5) Uani 1 1 d . . . . .
O2 O 0.3066(4) 0.27010(12) 0.5294(2) 0.0836(7) Uani 1 1 d . . . . .
N2 N 0.4445(3) 0.42261(11) 0.4044(2) 0.0494(5) Uani 1 1 d . . . . .
C2 C 0.5229(4) 0.50585(15) 0.2056(3) 0.0645(7) Uani 1 1 d . . . . .
H2A H 0.504041 0.459711 0.188831 0.077 Uiso 1 1 calc R U . . .
O3 O 0.3448(3) 0.57588(12) 0.61979(18) 0.0657(5) Uani 1 1 d . . . . .
N3 N 0.4637(3) 0.39022(11) 0.72027(19) 0.0522(5) Uani 1 1 d . . . . .
C3 C 0.5652(5) 0.54896(16) 0.1104(3) 0.0699(8) Uani 1 1 d . . . . .
H3A H 0.575009 0.531651 0.029042 0.084 Uiso 1 1 calc R U . . .
O4 O 0.2036(4) 0.73113(12) 0.4954(2) 0.0805(7) Uani 1 1 d . . . . .
N4 N 0.6888(6) 0.69482(18) -0.0487(3) 0.1080(12) Uani 1 1 d . . . . .
C4 C 0.5939(4) 0.61796(15) 0.1325(3) 0.0578(6) Uani 1 1 d . . . . .
N5 N 0.0388(3) 0.50662(11) 0.4338(2) 0.0505(5) Uani 1 1 d . . . . .
H5N H 0.076293 0.490293 0.510697 0.061 Uiso 1 1 d R U . . .
C5 C 0.5773(4) 0.64334(14) 0.2543(3) 0.0583(7) Uani 1 1 d . . . . .
H5A H 0.595144 0.689573 0.270598 0.070 Uiso 1 1 calc R U . . .
N6 N 0.0531(3) 0.57203(11) 0.39869(19) 0.0492(5) Uani 1 1 d . . . . .
C6 C 0.5347(4) 0.60059(14) 0.3506(3) 0.0555(6) Uani 1 1 d . . . . .
H6A H 0.523614 0.617980 0.431779 0.067 Uiso 1 1 calc R U . . .
N7 N 0.1105(3) 0.62183(11) 0.70896(19) 0.0526(5) Uani 1 1 d . . . . .
C7 C 0.3962(3) 0.38132(14) 0.4917(2) 0.0488(6) Uani 1 1 d . . . . .
N8 N -0.2072(6) 0.27253(17) -0.0125(3) 0.1071(13) Uani 1 1 d . . . . .
C8 C 0.3671(4) 0.30911(15) 0.4539(3) 0.0597(7) Uani 1 1 d . . . . .
C9 C 0.4134(5) 0.28704(18) 0.3247(3) 0.0788(9) Uani 1 1 d . . . . .
H9A H 0.412311 0.238091 0.320103 0.118 Uiso 1 1 calc R U . . .
H9B H 0.528844 0.303583 0.308883 0.118 Uiso 1 1 calc R U . . .
H9C H 0.328838 0.305261 0.261993 0.118 Uiso 1 1 calc R U . . .
C10 C 0.3489(3) 0.40268(13) 0.6227(2) 0.0484(6) Uani 1 1 d . . . . .
C11 C 0.6318(4) 0.35508(15) 0.7082(3) 0.0582(7) Uani 1 1 d . . . . .
H11A H 0.627993 0.331231 0.627378 0.070 Uiso 1 1 calc R U . . .
H11B H 0.647987 0.321299 0.775208 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7851(5) 0.4027(2) 0.7157(4) 0.0870(10) Uani 1 1 d . . . . .
H12A H 0.891972 0.377257 0.708795 0.130 Uiso 1 1 calc R U . . .
H12B H 0.789888 0.426331 0.795676 0.130 Uiso 1 1 calc R U . . .
H12C H 0.772091 0.435204 0.647578 0.130 Uiso 1 1 calc R U . . .
C13 C 0.4197(4) 0.41027(18) 0.8481(3) 0.0680(8) Uani 1 1 d . . . . .
H13A H 0.353552 0.452633 0.842628 0.082 Uiso 1 1 calc R U . . .
H13B H 0.528035 0.418726 0.899539 0.082 Uiso 1 1 calc R U . . .
C14 C 0.3155(7) 0.3584(3) 0.9117(4) 0.1127(15) Uani 1 1 d . . . . .
H14A H 0.288366 0.374787 0.993936 0.169 Uiso 1 1 calc R U . . .
H14B H 0.382478 0.316913 0.921120 0.169 Uiso 1 1 calc R U . . .
H14C H 0.208052 0.349682 0.861282 0.169 Uiso 1 1 calc R U . . .
C15 C 0.6448(5) 0.66135(17) 0.0314(3) 0.0743(9) Uani 1 1 d . . . . .
C16 C -0.0103(3) 0.45882(12) 0.3401(2) 0.0450(5) Uani 1 1 d . . . . .
C17 C -0.0183(4) 0.47585(14) 0.2117(3) 0.0624(7) Uani 1 1 d . . . . .
H17A H 0.008640 0.519943 0.186609 0.075 Uiso 1 1 calc R U . . .
C18 C -0.0663(5) 0.42709(16) 0.1222(3) 0.0694(8) Uani 1 1 d . . . . .
H18A H -0.070794 0.438354 0.036365 0.083 Uiso 1 1 calc R U . . .
C19 C -0.1078(4) 0.36161(14) 0.1583(2) 0.0568(6) Uani 1 1 d . . . . .
C20 C -0.0980(4) 0.34449(14) 0.2861(3) 0.0553(6) Uani 1 1 d . . . . .
H20A H -0.125149 0.300364 0.310917 0.066 Uiso 1 1 calc R U . . .
C21 C -0.0484(4) 0.39248(14) 0.3760(2) 0.0537(6) Uani 1 1 d . . . . .
H21A H -0.040143 0.380580 0.461572 0.064 Uiso 1 1 calc R U . . .
C22 C 0.1159(3) 0.61753(13) 0.4781(2) 0.0486(6) Uani 1 1 d . . . . .
C23 C 0.1306(4) 0.68775(15) 0.4284(3) 0.0590(7) Uani 1 1 d . . . . .
C24 C 0.0567(6) 0.70343(19) 0.2975(3) 0.0825(10) Uani 1 1 d . . . . .
H24A H 0.018849 0.750179 0.293323 0.124 Uiso 1 1 calc R U . . .
H24B H -0.041965 0.674060 0.276339 0.124 Uiso 1 1 calc R U . . .
H24C H 0.145702 0.696178 0.238319 0.124 Uiso 1 1 calc R U . . .
C25 C 0.1971(3) 0.60337(13) 0.6098(2) 0.0485(6) Uani 1 1 d . . . . .
C26 C -0.0676(4) 0.65124(14) 0.6954(3) 0.0594(7) Uani 1 1 d . . . . .
H26A H -0.075096 0.681367 0.622253 0.071 Uiso 1 1 calc R U . . .
H26B H -0.086220 0.678697 0.769981 0.071 Uiso 1 1 calc R U . . .
C27 C -0.2115(4) 0.59954(19) 0.6798(4) 0.0800(9) Uani 1 1 d . . . . .
H27A H -0.323496 0.622352 0.671457 0.120 Uiso 1 1 calc R U . . .
H27B H -0.207569 0.570220 0.752955 0.120 Uiso 1 1 calc R U . . .
H27C H -0.196165 0.572783 0.605068 0.120 Uiso 1 1 calc R U . . .
C28 C 0.1968(5) 0.61484(18) 0.8372(3) 0.0700(8) Uani 1 1 d . . . . .
H28A H 0.201211 0.659292 0.877900 0.084 Uiso 1 1 calc R U . . .
H28B H 0.317230 0.599655 0.830088 0.084 Uiso 1 1 calc R U . . .
C29 C 0.1062(6) 0.5660(3) 0.9194(4) 0.1128(16) Uani 1 1 d . . . . .
H29A H 0.173775 0.561001 0.999035 0.169 Uiso 1 1 calc R U . . .
H29B H 0.095376 0.522512 0.877758 0.169 Uiso 1 1 calc R U . . .
H29C H -0.008979 0.583142 0.934388 0.169 Uiso 1 1 calc R U . . .
C30 C -0.1612(5) 0.31150(16) 0.0633(3) 0.0748(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
O1 C10 1.239(3) . ?
N1 N2 1.335(3) . ?
N1 C1 1.392(3) . ?
N1 H1N 0.9000 . ?
C1 C2 1.389(4) . ?
C1 C6 1.393(4) . ?
O2 C8 1.215(4) . ?
N2 C7 1.296(3) . ?
C2 C3 1.365(4) . ?
C2 H2A 0.9300 . ?
O3 C25 1.243(3) . ?
N3 C10 1.327(3) . ?
N3 C13 1.463(4) . ?
N3 C11 1.464(3) . ?
C3 C4 1.386(4) . ?
C3 H3A 0.9300 . ?
O4 C23 1.215(4) . ?
N4 C15 1.137(4) . ?
C4 C5 1.391(4) . ?
C4 C15 1.436(4) . ?
N5 N6 1.340(3) . ?
N5 C16 1.394(3) . ?
N5 H5N 0.9001 . ?
C5 C6 1.370(4) . ?
C5 H5A 0.9300 . ?
N6 C22 1.292(3) . ?
C6 H6A 0.9300 . ?
N7 C25 1.321(3) . ?
N7 C28 1.470(4) . ?
N7 C26 1.470(4) . ?
C7 C8 1.482(4) . ?
C7 C10 1.509(4) . ?
N8 C30 1.142(4) . ?
C8 C9 1.493(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.490(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.476(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C21 1.389(4) . ?
C16 C17 1.391(4) . ?
C17 C18 1.375(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.380(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.386(4) . ?
C19 C30 1.441(4) . ?
C20 C21 1.370(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 C23 1.479(4) . ?
C22 C25 1.507(3) . ?
C23 C24 1.487(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 C27 1.492(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.489(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 118.1(2) . . ?
N2 N1 H1N 121.9 . . ?
C1 N1 H1N 118.9 . . ?
C2 C1 N1 121.7(2) . . ?
C2 C1 C6 119.5(2) . . ?
N1 C1 C6 118.8(2) . . ?
C7 N2 N1 121.2(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C10 N3 C13 119.1(2) . . ?
C10 N3 C11 123.5(2) . . ?
C13 N3 C11 117.4(2) . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C15 120.0(3) . . ?
C5 C4 C15 121.3(3) . . ?
N6 N5 C16 117.97(19) . . ?
N6 N5 H5N 124.2 . . ?
C16 N5 H5N 117.0 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C22 N6 N5 120.9(2) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6A 119.8 . . ?
C1 C6 H6A 119.8 . . ?
C25 N7 C28 119.1(2) . . ?
C25 N7 C26 122.3(2) . . ?
C28 N7 C26 118.6(2) . . ?
N2 C7 C8 116.7(2) . . ?
N2 C7 C10 124.9(2) . . ?
C8 C7 C10 118.0(2) . . ?
O2 C8 C7 118.7(3) . . ?
O2 C8 C9 122.5(3) . . ?
C7 C8 C9 118.8(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 N3 122.3(2) . . ?
O1 C10 C7 119.4(2) . . ?
N3 C10 C7 118.3(2) . . ?
N3 C11 C12 112.6(3) . . ?
N3 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 113.3(3) . . ?
N3 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
N3 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 C4 178.3(4) . . ?
C21 C16 C17 119.5(2) . . ?
C21 C16 N5 119.1(2) . . ?
C17 C16 N5 121.4(2) . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 C30 120.0(3) . . ?
C20 C19 C30 120.4(3) . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C20 C21 C16 120.4(2) . . ?
C20 C21 H21A 119.8 . . ?
C16 C21 H21A 119.8 . . ?
N6 C22 C23 116.4(2) . . ?
N6 C22 C25 125.5(2) . . ?
C23 C22 C25 117.5(2) . . ?
O4 C23 C22 119.1(3) . . ?
O4 C23 C24 121.7(3) . . ?
C22 C23 C24 119.2(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 N7 123.0(2) . . ?
O3 C25 C22 118.1(2) . . ?
N7 C25 C22 118.9(2) . . ?
N7 C26 C27 114.1(2) . . ?
N7 C26 H26A 108.7 . . ?
C27 C26 H26A 108.7 . . ?
N7 C26 H26B 108.7 . . ?
C27 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N7 C28 C29 113.5(3) . . ?
N7 C28 H28A 108.9 . . ?
C29 C28 H28A 108.9 . . ?
N7 C28 H28B 108.9 . . ?
C29 C28 H28B 108.9 . . ?
H28A C28 H28B 107.7 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N8 C30 C19 178.4(4) . . ?

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
N2 N1 C1 C2 0.4(4) . . . . ?
N2 N1 C1 C6 -179.3(2) . . . . ?
C1 N1 N2 C7 -175.7(2) . . . . ?
N1 C1 C2 C3 -179.0(3) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C2 C3 C4 C15 177.6(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C15 C4 C5 C6 -177.6(3) . . . . ?
C16 N5 N6 C22 -172.6(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
N1 C1 C6 C5 178.9(3) . . . . ?
N1 N2 C7 C8 177.6(2) . . . . ?
N1 N2 C7 C10 4.6(4) . . . . ?
N2 C7 C8 O2 -173.5(3) . . . . ?
C10 C7 C8 O2 0.0(4) . . . . ?
N2 C7 C8 C9 6.6(4) . . . . ?
C10 C7 C8 C9 -179.9(3) . . . . ?
C13 N3 C10 O1 1.2(4) . . . . ?
C11 N3 C10 O1 179.1(2) . . . . ?
C13 N3 C10 C7 -179.7(2) . . . . ?
C11 N3 C10 C7 -1.8(4) . . . . ?
N2 C7 C10 O1 73.8(3) . . . . ?
C8 C7 C10 O1 -99.1(3) . . . . ?
N2 C7 C10 N3 -105.3(3) . . . . ?
C8 C7 C10 N3 81.7(3) . . . . ?
C10 N3 C11 C12 104.0(3) . . . . ?
C13 N3 C11 C12 -78.1(3) . . . . ?
C10 N3 C13 C14 85.8(4) . . . . ?
C11 N3 C13 C14 -92.2(4) . . . . ?
N6 N5 C16 C21 -171.7(2) . . . . ?
N6 N5 C16 C17 9.6(3) . . . . ?
C21 C16 C17 C18 0.9(4) . . . . ?
N5 C16 C17 C18 179.6(3) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 C20 -1.2(5) . . . . ?
C17 C18 C19 C30 178.8(3) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C30 C19 C20 C21 -179.5(3) . . . . ?
C19 C20 C21 C16 1.0(4) . . . . ?
C17 C16 C21 C20 -1.7(4) . . . . ?
N5 C16 C21 C20 179.6(2) . . . . ?
N5 N6 C22 C23 178.3(2) . . . . ?
N5 N6 C22 C25 7.2(4) . . . . ?
N6 C22 C23 O4 -173.3(3) . . . . ?
C25 C22 C23 O4 -1.4(4) . . . . ?
N6 C22 C23 C24 6.4(4) . . . . ?
C25 C22 C23 C24 178.3(3) . . . . ?
C28 N7 C25 O3 5.0(4) . . . . ?
C26 N7 C25 O3 -177.0(3) . . . . ?
C28 N7 C25 C22 -173.6(3) . . . . ?
C26 N7 C25 C22 4.4(4) . . . . ?
N6 C22 C25 O3 71.8(3) . . . . ?
C23 C22 C25 O3 -99.3(3) . . . . ?
N6 C22 C25 N7 -109.6(3) . . . . ?
C23 C22 C25 N7 79.3(3) . . . . ?
C25 N7 C26 C27 83.2(3) . . . . ?
C28 N7 C26 C27 -98.8(3) . . . . ?
C25 N7 C28 C29 -117.0(3) . . . . ?
C26 N7 C28 C29 64.9(4) . . . . ?

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 H1N O3 0.90 1.99 2.847(3) 159.7 . yes
N5 H5N O1 0.90 1.96 2.819(3) 158.0 . yes

_refine_diff_density_max         0.113
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_010119_LIK6
_database_code_depnum_ccdc_archive 'CCDC 1963604'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 Cl N3 O2'
_chemical_formula_sum            'C12 H14 Cl N3 O2'
_chemical_formula_weight         267.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.998(2)
_cell_length_b                   7.5198(9)
_cell_length_c                   18.740(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.185(3)
_cell_angle_gamma                90
_cell_volume                     2516.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6003
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.24

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.302
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16901
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.479
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6111
_reflns_number_gt                4693
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+2.1058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6111
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.57944(3) 0.16424(8) 0.02550(3) 0.02639(14) Uani 1 1 d . . . . .
Cl2 Cl 0.02693(3) 0.30297(8) 1.06805(3) 0.02692(14) Uani 1 1 d . . . . .
O1 O 0.28045(8) 0.5960(2) 0.30778(8) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.12001(8) 0.7411(2) 0.17421(8) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.34116(9) 0.4294(2) 0.18826(8) 0.0158(3) Uani 1 1 d . . . . .
H1N H 0.346711 0.415390 0.236322 0.019 Uiso 1 1 d R U . . .
N2 N 0.28177(9) 0.5088(2) 0.15394(9) 0.0155(3) Uani 1 1 d . . . . .
N3 N 0.16774(9) 0.4579(2) 0.29185(9) 0.0180(4) Uani 1 1 d . . . . .
N4 N 0.19070(9) 0.0241(2) 0.83799(8) 0.0168(3) Uani 1 1 d . . . . .
H4N H 0.240494 0.042137 0.842218 0.020 Uiso 1 1 d R U . . .
N5 N 0.15300(9) -0.0519(2) 0.78074(8) 0.0154(3) Uani 1 1 d . . . . .
N6 N 0.28880(9) 0.0167(2) 0.66324(9) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.39806(10) 0.3711(3) 0.14890(10) 0.0149(4) Uani 1 1 d . . . . .
C2 C 0.46356(11) 0.3003(3) 0.18564(10) 0.0162(4) Uani 1 1 d . . . . .
H2A H 0.469637 0.294923 0.236684 0.019 Uiso 1 1 calc R U . . .
C3 C 0.51996(11) 0.2375(3) 0.14806(11) 0.0177(4) Uani 1 1 d . . . . .
H3A H 0.564473 0.188532 0.173032 0.021 Uiso 1 1 calc R U . . .
C4 C 0.51045(11) 0.2472(3) 0.07385(11) 0.0188(4) Uani 1 1 d . . . . .
C5 C 0.44582(12) 0.3187(3) 0.03664(11) 0.0230(5) Uani 1 1 d . . . . .
H5A H 0.440068 0.324472 -0.014397 0.028 Uiso 1 1 calc R U . . .
C6 C 0.38981(11) 0.3814(3) 0.07425(11) 0.0210(4) Uani 1 1 d . . . . .
H6A H 0.345660 0.431513 0.049056 0.025 Uiso 1 1 calc R U . . .
C7 C 0.22618(10) 0.5583(3) 0.18721(10) 0.0147(4) Uani 1 1 d . . . . .
C8 C 0.22620(11) 0.5383(3) 0.26793(10) 0.0167(4) Uani 1 1 d . . . . .
C9 C 0.16384(13) 0.4453(3) 0.36912(11) 0.0233(5) Uani 1 1 d . . . . .
H9A H 0.205289 0.512533 0.395231 0.035 Uiso 1 1 calc R U . . .
H9B H 0.167506 0.320288 0.383942 0.035 Uiso 1 1 calc R U . . .
H9C H 0.116114 0.494552 0.379985 0.035 Uiso 1 1 calc R U . . .
C10 C 0.10613(11) 0.3763(3) 0.24546(11) 0.0213(4) Uani 1 1 d . . . . .
H10A H 0.120492 0.360563 0.197114 0.032 Uiso 1 1 calc R U . . .
H10B H 0.061897 0.453102 0.242957 0.032 Uiso 1 1 calc R U . . .
H10C H 0.094529 0.260175 0.265113 0.032 Uiso 1 1 calc R U . . .
C11 C 0.16773(11) 0.6647(3) 0.14446(10) 0.0158(4) Uani 1 1 d . . . . .
C12 C 0.16800(11) 0.6807(3) 0.06434(10) 0.0202(4) Uani 1 1 d . . . . .
H12A H 0.164844 0.806470 0.050527 0.030 Uiso 1 1 calc R U . . .
H12B H 0.124949 0.616543 0.039470 0.030 Uiso 1 1 calc R U . . .
H12C H 0.214397 0.629685 0.050920 0.030 Uiso 1 1 calc R U . . .
C13 C 0.15110(11) 0.0828(3) 0.89339(10) 0.0159(4) Uani 1 1 d . . . . .
C14 C 0.19081(11) 0.1353(3) 0.95868(10) 0.0179(4) Uani 1 1 d . . . . .
H14A H 0.243877 0.126601 0.965803 0.021 Uiso 1 1 calc R U . . .
C15 C 0.15289(11) 0.2002(3) 1.01320(11) 0.0192(4) Uani 1 1 d . . . . .
H15A H 0.179654 0.235956 1.057809 0.023 Uiso 1 1 calc R U . . .
C16 C 0.07552(11) 0.2122(3) 1.00183(11) 0.0194(4) Uani 1 1 d . . . . .
C17 C 0.03526(11) 0.1563(3) 0.93804(11) 0.0213(4) Uani 1 1 d . . . . .
H17A H -0.017870 0.162737 0.931560 0.026 Uiso 1 1 calc R U . . .
C18 C 0.07318(11) 0.0908(3) 0.88372(11) 0.0187(4) Uani 1 1 d . . . . .
H18A H 0.046019 0.051303 0.839844 0.022 Uiso 1 1 calc R U . . .
C19 C 0.18588(10) -0.0936(3) 0.72499(10) 0.0149(4) Uani 1 1 d . . . . .
C20 C 0.26813(11) -0.0635(3) 0.72152(10) 0.0167(4) Uani 1 1 d . . . . .
C21 C 0.36798(11) 0.0306(3) 0.65417(12) 0.0234(5) Uani 1 1 d . . . . .
H21A H 0.397932 -0.035671 0.692604 0.035 Uiso 1 1 calc R U . . .
H21B H 0.383072 0.155869 0.656400 0.035 Uiso 1 1 calc R U . . .
H21C H 0.376086 -0.019135 0.607427 0.035 Uiso 1 1 calc R U . . .
C22 C 0.23659(12) 0.0937(3) 0.60605(11) 0.0236(5) Uani 1 1 d . . . . .
H22A H 0.188183 0.113569 0.623568 0.035 Uiso 1 1 calc R U . . .
H22B H 0.230006 0.012238 0.564944 0.035 Uiso 1 1 calc R U . . .
H22C H 0.256389 0.207376 0.591118 0.035 Uiso 1 1 calc R U . . .
C23 C 0.14041(11) -0.1994(3) 0.66890(10) 0.0168(4) Uani 1 1 d . . . . .
O3 O 0.31312(8) -0.1129(2) 0.77296(8) 0.0255(3) Uani 1 1 d . . . . .
O4 O 0.17012(8) -0.2658(2) 0.62003(8) 0.0222(3) Uani 1 1 d . . . . .
C24 C 0.05817(11) -0.2240(3) 0.67289(11) 0.0213(4) Uani 1 1 d . . . . .
H24A H 0.041840 -0.338223 0.651170 0.032 Uiso 1 1 calc R U . . .
H24B H 0.030110 -0.127369 0.646772 0.032 Uiso 1 1 calc R U . . .
H24C H 0.048936 -0.222320 0.723323 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7415(19) . ?
Cl2 C16 1.744(2) . ?
O1 C8 1.232(2) . ?
O2 C11 1.224(2) . ?
N1 N2 1.319(2) . ?
N1 C1 1.405(2) . ?
N1 H1N 0.8999 . ?
N2 C7 1.298(2) . ?
N3 C8 1.338(2) . ?
N3 C10 1.456(3) . ?
N3 C9 1.462(2) . ?
N4 N5 1.325(2) . ?
N4 C13 1.402(2) . ?
N4 H4N 0.9000 . ?
N5 C19 1.302(2) . ?
N6 C20 1.340(3) . ?
N6 C22 1.455(3) . ?
N6 C21 1.460(2) . ?
C1 C6 1.390(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.388(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(3) . ?
C5 C6 1.383(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C11 1.475(3) . ?
C7 C8 1.520(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.507(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.393(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.386(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.384(3) . ?
C17 C18 1.385(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C23 1.481(3) . ?
C19 C20 1.507(3) . ?
C20 O3 1.236(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O4 1.223(2) . ?
C23 C24 1.503(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 118.97(16) . . ?
N2 N1 H1N 121.5 . . ?
C1 N1 H1N 119.5 . . ?
C7 N2 N1 121.46(16) . . ?
C8 N3 C10 124.21(17) . . ?
C8 N3 C9 119.89(18) . . ?
C10 N3 C9 115.88(17) . . ?
N5 N4 C13 118.61(16) . . ?
N5 N4 H4N 122.7 . . ?
C13 N4 H4N 118.7 . . ?
C19 N5 N4 121.03(16) . . ?
C20 N6 C22 124.05(17) . . ?
C20 N6 C21 120.11(18) . . ?
C22 N6 C21 115.84(17) . . ?
C6 C1 C2 119.68(18) . . ?
C6 C1 N1 121.19(18) . . ?
C2 C1 N1 119.13(17) . . ?
C3 C2 C1 120.40(18) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 119.09(18) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C3 C4 C5 121.11(18) . . ?
C3 C4 Cl1 119.88(16) . . ?
C5 C4 Cl1 118.99(16) . . ?
C6 C5 C4 119.64(19) . . ?
C6 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
C5 C6 C1 120.06(19) . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
N2 C7 C11 115.78(17) . . ?
N2 C7 C8 123.04(17) . . ?
C11 C7 C8 120.36(16) . . ?
O1 C8 N3 123.55(18) . . ?
O1 C8 C7 118.04(17) . . ?
N3 C8 C7 118.41(17) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C7 120.03(17) . . ?
O2 C11 C12 120.39(18) . . ?
C7 C11 C12 119.57(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.94(18) . . ?
C18 C13 N4 120.94(18) . . ?
C14 C13 N4 119.12(17) . . ?
C15 C14 C13 120.05(18) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C16 C15 C14 119.19(19) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C17 C16 C15 121.38(18) . . ?
C17 C16 Cl2 118.60(16) . . ?
C15 C16 Cl2 120.01(16) . . ?
C16 C17 C18 119.36(19) . . ?
C16 C17 H17A 120.3 . . ?
C18 C17 H17A 120.3 . . ?
C17 C18 C13 120.03(19) . . ?
C17 C18 H18A 120.0 . . ?
C13 C18 H18A 120.0 . . ?
N5 C19 C23 115.64(17) . . ?
N5 C19 C20 123.10(17) . . ?
C23 C19 C20 120.59(16) . . ?
O3 C20 N6 123.31(18) . . ?
O3 C20 C19 118.19(17) . . ?
N6 C20 C19 118.50(17) . . ?
N6 C21 H21A 109.5 . . ?
N6 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N6 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 H22A 109.5 . . ?
N6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 C19 119.76(18) . . ?
O4 C23 C24 120.83(18) . . ?
C19 C23 C24 119.42(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C7 177.02(18) . . . . ?
C13 N4 N5 C19 173.54(18) . . . . ?
N2 N1 C1 C6 -5.7(3) . . . . ?
N2 N1 C1 C2 174.88(18) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
N1 C1 C2 C3 178.38(18) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 Cl1 -178.42(16) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
Cl1 C4 C5 C6 178.55(18) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
N1 C1 C6 C5 -178.3(2) . . . . ?
N1 N2 C7 C11 172.80(17) . . . . ?
N1 N2 C7 C8 3.1(3) . . . . ?
C10 N3 C8 O1 -174.8(2) . . . . ?
C9 N3 C8 O1 4.0(3) . . . . ?
C10 N3 C8 C7 4.7(3) . . . . ?
C9 N3 C8 C7 -176.53(18) . . . . ?
N2 C7 C8 O1 51.2(3) . . . . ?
C11 C7 C8 O1 -118.1(2) . . . . ?
N2 C7 C8 N3 -128.3(2) . . . . ?
C11 C7 C8 N3 62.5(3) . . . . ?
N2 C7 C11 O2 -168.07(19) . . . . ?
C8 C7 C11 O2 1.9(3) . . . . ?
N2 C7 C11 C12 10.9(3) . . . . ?
C8 C7 C11 C12 -179.11(18) . . . . ?
N5 N4 C13 C18 -11.3(3) . . . . ?
N5 N4 C13 C14 169.38(18) . . . . ?
C18 C13 C14 C15 -1.8(3) . . . . ?
N4 C13 C14 C15 177.52(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C17 1.8(3) . . . . ?
C14 C15 C16 Cl2 -177.05(16) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
Cl2 C16 C17 C18 177.32(17) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 2.1(3) . . . . ?
N4 C13 C18 C17 -177.24(19) . . . . ?
N4 N5 C19 C23 171.97(17) . . . . ?
N4 N5 C19 C20 1.4(3) . . . . ?
C22 N6 C20 O3 -172.7(2) . . . . ?
C21 N6 C20 O3 7.3(3) . . . . ?
C22 N6 C20 C19 6.8(3) . . . . ?
C21 N6 C20 C19 -173.21(18) . . . . ?
N5 C19 C20 O3 48.2(3) . . . . ?
C23 C19 C20 O3 -122.0(2) . . . . ?
N5 C19 C20 N6 -131.3(2) . . . . ?
C23 C19 C20 N6 58.6(3) . . . . ?
N5 C19 C23 O4 -169.48(19) . . . . ?
C20 C19 C23 O4 1.4(3) . . . . ?
N5 C19 C23 C24 10.4(3) . . . . ?
C20 C19 C23 C24 -178.70(18) . . . . ?

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 H1N O1 0.90 2.34 2.897(2) 120.3 . yes
N1 H1N O2 0.90 2.15 2.947(2) 146.7 2_545 yes
N4 H4N O3 0.90 2.28 2.841(2) 120.6 . yes
N4 H4N O4 0.90 2.21 2.983(2) 143.5 2_556 yes
C2 H2A O2 0.95 2.50 3.217(2) 132.7 2_545 yes
C3 H3A O3 0.95 2.38 3.314(2) 169.3 3_656 yes
C10 H10A Cl2 0.98 2.80 3.494(2) 128.1 1_554 yes
C14 H14A O4 0.95 2.50 3.149(2) 125.4 2_556 yes
C21 H21B N5 0.98 2.61 3.407(3) 138.1 2_556 yes

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.065

